bluuebunny/crossref_metadata_2025 huggingface dataset:
ChemInform Abstract: SYNTHESIS OF 12‐ AND 13‐HYDROXYSTEARIC ACIDS FROM 1,5,9‐CYCLODODECATRIENE
Authors: ZAKHARKIN L. I. , GUSEVA V. V. , CHURILOVA I. M. , MASKAEV A. K. , KOBILINSKAYA I. F. , TANCHUK YU. V.
Published: April 2016

Eine Grignard‐Reaktion des aus Cyclododecatrien‐( l ,5,9) zugänglichen Cyanaldehyds (I) mit Hexyl‐MgCl liefert bei nachfolgender alkalischer Hydrolyse des Hydroxynitrils (II) 12‐Hydroxy‐stearinsäure (III); auch das aus dem Cyclotrien erhaltene Oxim (IV) läßt sich über eine Grignard‐Reaktion in (III) überführen.
ChemInform Abstract: SYNTHESIS OF RACEMIC TRANS‐6‐HYDROXY‐5‐METHYL‐2‐HEPTENE‐3,6‐DICARBOXYLIC ACID (INTEGERRINECIC ACID)
Authors: PASTEWKA U. , WIEDENFELD H. , ROEDER E. +
Published: April 2016

Ausgehend von Ethylmalonsäureester (I) wird die im Titel genannte Verbindung (V) in einer mehrstufigen Reaktionsfolge hergestellt.
ChemInform Abstract: SYNTHESIS OF AMINO ACIDS AND RELATED COMPOUNDS. PART XXII. SYNTHESES AND ANTIMICROBIAL ACTIVITIES OF α‐ISOCYANOACRYLIC ACID DERIVATIVES
Authors: SUZUKI M. , NUNAMI K. , MATSUMOTO K. , YONEDA N. , KASUGA O. , YOSHIDA H. , YAMAGUCHI T.
Published: April 2016

Zur Untersuchung ihrer antimikrobiellen Aktivität werden eine Reihe von α‐Isocyanoacrylsäurederivaten (IV) aus den entsprechenden Carbonylverbindungen (I) und Isocyanoessigsäurederivaten (II) über die α‐Formylaminoverbindungen (III) hergestellt.
ChemInform Abstract: OXIDATION PRODUCTS OF ARACHIDONIC ACID. II. THE SYNTHESIS OF METHYL 8R,9S,11R‐TRIHYDROXY‐5Z,12E,14Z‐EICOSATRIENOATE
Authors: JUST G. , LUTHE C.
Published: April 2016

Ausgehend von dem Glucosediacetonid (Ia) wird nach angegebenem Schema stereospezifisch der Tite1ester(VIIIc) synthetisiert; Schlüsselverbindungen der Synthese sind die Anhydrodesoxyglucofuranose (II) und das Dodecanoat (VIIb) ‐ ein wichtiges Zwischenprodukt in der Synthese von Oxidationsprodukten der Arachidonsäure.
ChemInform Abstract: PREPARATION AND DIELS‐ALDER REACTIONS OF SOME FUNCTIONALIZED ISOPRENES
Authors: MANDAI T. , YOKOYAMA H. , MIKI T. , FUKUDA H. , KOBATA H. , KAWADA M. , OTERA J.
Published: April 2016

Auf dem im Formelschema angegebenen Weg wird das Sulfoxid (V) synthetisiert, das bei der Thermolyse nicht den monomeren α‐Methylen‐buten‐säureester sondern die durch Dimerisierung entstandenen Cyclohexendicarbonsäureester (VI) liefert.
ChemInform Abstract: CYCLOADDITION OF ALLYL CATIONS. 23. SYNTHESIS OF NORBORNENE DERIVATIVES FROM CYCLOPENTADIENE AND ALLYL ALCOHOLS IN AN ACIDIC TWO‐PHASE SYSTEM
Authors: ERNST H. , HOFFMANN H. M. R.
Published: April 2016

Das aus dem Dimethylpentenol (I) in einem Zweiphasensystem aus wäßriger p‐Toluolsulfonsäure und Pentan erzeugte Anion liefert mit Cyclopentadien (II) die Alkohole (III) und (IV) (besteht mindestens aus drei monocyclischen Isomeren), die Bicyclodiene (V) und (VI) sowie zwei allylsubstituierte Cyclopentadiene.
ChemInform Abstract: SYNTHESIS OF ADAMANTANE DERIVATIVES. 49. SUBSTITUTION REACTION OF 1‐ADAMANTYL L CHLORIDE WITH SOME TRIMETHYLSILYLATED UNSATURATED COMPOUNDS
Authors: SASAKI T. , USUKI A. , OHNO M.
Published: April 2016

1‐Adamantylchlorid (I) reagiert mit Allyltrimethylsilan (II) in Gegenwart von TiCl4 zum Allyladamantan (III).
ChemInform Abstract: SYNTHESIS OF SOME AROMATIC DIISOCYANIDES WITH TRICHLOROMETHYL CHLOROFORMATE
Authors: EFRATY A. , FEINSTEIN I. , WACKERLE L. , GOLDMAN A.
Published: April 2016

Aus den aromatischen Bis‐formylaminen (I) erhält man mit Chlorkohlensäuretrichlormethylester (II) in Gegenwart von Triethylamin die Isonitrile (III).
ChemInform Abstract: PREPARATION OF β‐HYDROXY‐α‐PHENYLTHIO ESTERS VIA CONDENSATION OF ALDEHYDES WITH α‐PHENYLTHIOESTER ENOLATE ANIONS
Authors: HOYE T. R. , KURTH M. J.
Published: April 2016

Phenyl‐ bzw. Methylthioessigester (I) reagieren über die Li‐enolate mit den Aldehyden (II) zu den Addukten (III), die mit dem 2‐Fluor‐1‐ethyl‐pyridiniumsalz (IV) zu (V) verethert und weiter zu den Olefinen (VI) eliminiert werden.
ChemInform Abstract: PREPARATION AND IR‐SPECTROSCOPIC STUDY OF CHARGE TRANSFER COMPLEXES OF NAPHTHALENE DERIVATIVES WITH SOME TRI‐ AND DI‐NITROBENZENES
Authors: HINDAWEY A. M. , ISSA Y. M. , MARGHALANI Y. A. , ISSA R. M.
Published: April 2016

Aus den Verschiebungen der Bandenlagen bei der Komplexierung bzw. aus der Abhängigkeit der Bandenlagen von der funktionellen Gruppe wird für die aus den Naphthalin‐Donatoren und Di‐ und Trinitrobenzol‐Akzeptoren gebildeten, verschieden farbigen 1:1‐CT‐Komplexen (I) der Bindungstyp ermittelt.
ChemInform Abstract: EFFECT OF ELECTROPHILIC AGENTS ON POLYFLUOROAROMATIC COMPOUNDS. XVI. REACTION N OF POLYFLUORINATED NAPHTHALENES AND DIHYDRONAPHTHALENES WITH PENTAFLUOROBENZENE IN AN ANTIMONY PENTAFLUORIDE MEDIUM
Authors: SELIVANOV B. A. , POZDNYAKOVICH YU. V. , CHUIKOVA T. V. , OSINA O. I. , SHTEINGARTS V. D.
Published: April 2016

Die Polyfluornaphthaline (I) reagieren mit äquimolaren Mengen von Pentafluorbenzol in SbF5 unter Bildung von Gemischen der Substitutionsprodukte (II) mit den substituierten Chinonen (III); im Falle (a) entsteht außerdem 1,5‐Bis‐(pentafluorphenyl)‐hexafluornaphthalin (Ausb. 15%).
ChemInform Abstract: TRICYCLO(4.2.2.01,6)DECANE‐TRICYCLO(4.2.2.01,5)DECANE INTERCONVERSIONS. (4.2.2)PROPELLANE REARRANGEMENTS AND A NONPHOTOCHEMICAL PROPELLANE SYNTHESIS
Authors: EATON P. E. , JOBE P. G. , NYI K.
Published: April 2016

Behandlung des Propellanketons (I) mit verschiedenen Säuren (keine näheren Angaben) liefert die Umlagerungsprodukte (II).
ChemInform Abstract: PROMOTED DIMERIZATION OF α‐METHYLSTYRENE BY 3,5‐DIMETHOXY SUBSTITUENTS
Authors: SCHMITT B. , BIRR C.
Published: April 2016

Bei der Abspaltung der Schutzgruppe aus Peptiden (I) mit Trifluoressigsäure erhält man das Dimerisierungsprodukt des Dimethoxy‐a‐methylstyrols (II).
ChemInform Abstract: SYNTHESIS AND REACTIONS OF 2‐LITHIO‐3‐CHLOROBICYCLO(2.2.1)HEPT‐2‐ENE. GENERATION OF THE TRIMER OF BICYCLO(2.2.1)HEPT‐2‐YNE
Authors: GASSMAN P. G. , GENNICK I.
Published: April 2016

Das Chlorbicyclohepten (I) reagiert mit 1 Äquiv.
ChemInform Abstract: INTRAMOLECULAR CYCLIZATION OF EPOXY ALCOHOLS. IV. STERIC EFFECT IN REGIOSELECTIVE CYCLIZATION OF 3,4‐EPOXY ALCOHOLS TO OXETANES
Authors: MASAMUNE T. , SATO S. , ABIKO A. , ONO M. , MURAI A.
Published: April 2016

Eine Reihe von Epoxyalkoholen wie (I), (IV), (VII) (Darstellung beschrieben), die für die Oxetanbildung [→(II), (V), (VIII)] durch intramolekulare Cyclisierung kritische Strukturmerkmale aufweisen, R4 werden mit Base unter wäßrigen (a)) und unter wasserfreien Bedingungen (b)) behandelt; desgleichen werden zum Vergleich Reaktionen der Epoxide (XI) durchgeführt.
ChemInform Abstract: 3‐(PHENYLSELENO)‐2‐PROPENAL AS A VERSATILE UNIT FOR OXETANE RING FORMATION
Authors: SHIMIZU M. , KUWAJIMA I.
Published: April 2016

Aus den Alkoholen (I) werden oxidativ die Aldehyde (II) hergestellt und mit Grignard‐ oder Li‐Verbindungen zu den Addukten (III) umgesetzt.
ChemInform Abstract: UNUSUAL CYCLIZATION OF 1,2‐DIBENZOYLCYCLOHEXA‐1,4‐DIENE DURING CATALYTIC HYDROGENATION
Authors: SINHA A. , LAHIRI S.
Published: April 2016

Bei der katalytischen Hydrierung der Dibenzoyl‐cyclohexadiene (I) entstehen die kondensierten Furane (IIa) bzw. (IIIa) und (IIIb).
ChemInform Abstract: REDUCTIVE METALATION OF 1,3‐DIPHENYLISOBENZOFURAN. STEREOSELECTIVE FORMATION OF CIS PRODUCTS
Authors: SMITH J. G. , MCCALL R. B.
Published: April 2016

1,3‐Diphenylisobenzofuran (I) liefert ein Dianion (II), aus dem die Reaktionsprodukte (IIIa)‐(IIId) durch Behandlung mit Säuren, Kohlendioxid, anschließende Veresterung oder Methylierung erhalten werden.
ChemInform Abstract: α‐HETEROSUBSTITUTED PHOSPHONATE CARBANIONS. 11. BENZOINS VIA AN ACYL ANION EQUIVALENT. NOVEL ONE‐POT PREPARATION OF BENZO(B)FURANS VIA BENZOINS USING HYDRIODIC ACID
Authors: KOENIGKRAMER R. E. , ZIMMER H.
Published: April 2016

Triethylphosphit (I), Benzaldehyd (II) und Trimethylchlorsilan (III) reagieren zu dem Kondensat (IV), das zu (V) metalliert wird.
ChemInform Abstract: ANALOGS OF PROPRANOLOL. SYNTHESIS OF 3‐ALKYLAMINO‐1‐(3‐BENZO(B)THIENYLOXY)‐2‐PROPANOLS
Authors: CONDE S. , CORRAL C. , LISSAVETZKY J.
Published: April 2016

3‐Hydroxy‐benzothiophen‐2‐carbonsäureester (Ia) liefert den Glycidylester (Ib), der mit verschiedenen Aminen zu den Reaktionsprodukten (II) führt.
ChemInform Abstract: REARRANGEMENT OF α‐ACETYLENIC ALCOHOLS SUBSTITUTED WITH Δ1‐PYRROLINE
Authors: DANNHARDT G. , OBERGRUSBERGER R.
Published: April 2016

Durch 1,2‐Addition der Pyrroline (I) an die Propargylaldehyde (II) entstehen die Acetylenalkohole (III), deren thermische Umlagerung in Abhängigkeit von den Substituenten untersucht wird.
ChemInform Abstract: PREVENTION OF AMES TEST MUTAGENICITY BY CHEMICAL MODIFICATION IN A SERIES OF MONOAMINE OXIDASE INHIBITORS
Authors: HARFENIST M.
Published: April 2016

Die Verbindung (I) inhibiert in vitro und in vivo Monoaminooxidase und zeigt im Ames‐Test mutagene Wirkung.
ChemInform Abstract: SYNTHETIC CONTROL BY INTERNAL HYDROGEN BONDING. THE INTRAMOLECULAR DIELS‐ALDER REACTION OF NITROFURAN AND α,β‐UNSATURATED CARBOXAMIDES
Authors: MUKAIYAMA T. , TAKEBAYASHI T.
Published: April 2016

Die Methacrylamide (I) gehen durch intramolekulare Diels‐Alder‐Reaktion in die Polycyclen (II) über.
ChemInform Abstract: THIAPEN CHEMISTRY: SYNTHESIS OF HIGHER HOMOLOGS OF TETRATHIAFULVALENE
Authors: SCHUMAKER R. R. , ENGLER E. M.
Published: April 2016

Erhitzen von Thiapendion (I) mit den Dithiolen (II) liefert die Produkte (III)‐(VI); durch Wahl bestimmter Reaktionsbedingungen ist die selektive Darstellung von (III) bzw. (IV) möglich [→(IIIa) bzw. (IVb), (IVc)].
ChemInform Abstract: CYCLIZATION OF DINITROPHENYL TERT‐BUTYL TRITHIOCARBONATES. A NOVEL SYNTHESIS OF NITRO‐1,3‐BENZODITHIOLE‐2‐THIONES
Authors: RASHEED K. , WARKENTIN J. D.
Published: April 2016

Aus den 2,6‐Dinitro‐chlorbenzolen (I) entstehen mit tert.‐Butyltrithiokohlensäure‐natrium (II) über die Trithiocarbonate (III) die Cyclisierungsprodukte (IV) mit 1,3‐Benzodithiol‐2‐thion‐Struktur.
ChemInform Abstract: A NEW REARRANGEMENT OF SPIRO‐3H‐PYRAZOLES
Authors: MATAKA S. , TAKAHASHI K. , OHSHIMA T. , TASHIRO M.
Published: April 2016

Die Diazoverbindungen (I) reagieren mit Acetylendicarbonsäuredimethylester (II) im Sinne einer 1,3‐dipolaren Cycloaddition zu den Spiropyrazolen (III), die bei der Thermolyse entweder Stickstoff abspalten und in Spirocyclopropene (IV) übergehen oder zu den Pyrazolen (V) und (VI) isomerisieren.
ChemInform Abstract: AN EASILY INTRODUCED AND REMOVED PROTECTING GROUP FOR IMIDAZOLE NITROGEN: A CONVENIENT ROUTE TO 2‐SUBSTITUTED IMIDAZOLES
Authors: CURTIS N. J. , BROWN R. S.
Published: April 2016

Imidazole (I) werden mit Orthoamei‐ sensäureester in die 1‐Diethoxymethyl‐imidazole (II) umgewandelt und dann zu den 2‐Lithio‐imidazolen (III) bei niederer Temperatur metalliert.
ChemInform Abstract: PREPARATION AND STEREOCHEMISTRY OF 4‐ARYL‐3‐BUTENYLAMINES. A NOVEL SYNTHESIS OF AN OXAZOLO(2,3‐A)ISOINDOLE
Authors: OLSEN D. K. , TORIAN B. E. , MORGAN C. D. , BRAUN L. L.
Published: April 2016

Aus den Benzaldehyden (I) und dem P‐Ylid (II) entstehen die Olefine (III), die nach Spaltung der Schutzgruppe zu den entsprechenden ungesättigten Aminen (IV) führen.
ChemInform Abstract: BENZO‐Γ‐PYRONES. PART VIII. REACTION OF CHALCONE DIBROMIDES AND β‐DIKETONES WITH HYDROXYLAMINE
Authors: MAIB P. , BASINSKI W. , JERZMANOWSKA Z.
Published: April 2016

Die isomeren Chalkondibromide (I) bzw. (IV) cyclisieren mit HO‐NH2·H2O zu einem Gemisch aus den isomeren Isoxazolen (II) und (III); die Reaktion verläuft analog mit dem Dibromchalkon (V), das die Isoxazole (VI) und (VII) gibt.
ChemInform Abstract: SYNTHESIS AND STRUCTURE OF COMPOUNDS PRODUCED WITH ACYLATION OF 6‐PHENYLAMINO‐5,11‐NAPHTHACENEQUINONE
Authors: GERASIMENKO YU. E. , POTELESHCHENKO N. T. , ROMANOV V. V.
Published: April 2016

Die bei H2SO4‐katalysierten Reaktionen der Titelverbindung (I) mit Essig‐ oder Benzoesäureanhydrid entstehenden N‐Acylierungsprodukte (II) gehen in unpolaren Medien in die . acylotropen Tautomeren (III) über (IR‐, VIS‐Spektrum).
ChemInform Abstract: SYNTHESIS OF SOME FUROCHROMENES WHICH ARE PHARMACOCHEMICAL ANALOGS OF XANTHYLETIN AND SESELIN
Authors: RENE L. , FAULQUES M. , ROYER R.
Published: April 2016

Aus den isomeren Hydroxy‐aldehyden (I) und (IV) erhält man durch Kondensation mit Chloressigsäureester (II) in basischem Milieu die kondensierten Carbonsäureester (IIIa) bzw. (IVa).
ChemInform Abstract: SYNTHESIS AND SPECTRAL DATA OF SOME HETEROCYCLIC COMPOUNDS. THE REACTION OF ARYLPROPIOLIC ESTERS WITH TETRALONES AND ACETYLCYCLOPROPANE
Authors: AL‐JOBOUR N. H. , SHANDALA M. Y.
Published: April 2016

Phenylpropiolsäureester (I) kondensiert mit den 1‐Tetralonen (II) zu den Naphthopyranonen (III), während die 2‐Tetralone (IV) die Michael‐Addukte (V) ergeben.
ChemInform Abstract: SYNTHESIS OF DIPYRIDYL SULFIDES FROM PYRIDYLPYRIDINIUM HALIDES
Authors: BODUSZEK B. , WIECZOREK J. S.
Published: April 2016

Die Pyridylpyridiniumsalze (II) bzw. (VII) kondensieren mit den Thiolpyridinen (III) bzw. (V) zu den neuartigen Dipyridylsulfiden (IV) bzw. (VI) bzw. (VIII).
ChemInform Abstract: HETEROCYCLIC β‐DIKETOENAMINES. 2. C‐ AND N‐SUBSTITUTED 2‐(4‐PYRIDYL)‐1,3‐INDANEDIONES
Authors: PLOQUIN J. , SPARFEL L. , LE BAUT G. , FLOC'H R.
Published: April 2016

Die 2‐Pyridyl‐1,3‐indandione (I) liefern die isomeren Formen (II), die in 4′‐Stellung zu (IV) substituiert werden können.
ChemInform Abstract: INTRAMOLECULAR ALKYLATIONS OF AROMATIC COMPOUNDS. PART 9. SYNTHESIS OF N‐METHYL‐8‐(3‐METHOXYBENZYL)‐1,2,3,5,6,7,8,8A‐OCTAHYDROQUINOLINE AND N‐METHYL‐9‐(3‐METHOXYBENZYL)‐1,2,3,6,7,8,9,9A‐OCTAHYDRO‐5H‐CYCLOHEPTA(B)PYRIDINE
Authors: DAMMERTZ W. , REIMANN E.
Published: April 2016

Die Kondensation der Alkenopyridine (I) mit 3‐Methoxybenzaldehyd (II) liefert die Benzylidenderivate (III), die nach katalytischer Hydrierung die Benzylverbindungen (IV) ergeben.
ChemInform Abstract: STUDIES ON TERTIARY AMINE OXIDES. LXVIII. REACTIONS OF AROMATIC N‐OXIDES WITH H 2‐SUBSTITUTED 2‐OXAZOLIN‐5‐ONES IN THE PRESENCE OF ACETIC ANHYDRIDE
Authors: YOUSIF M. M. , SAEKI S. , HAMANA M.
Published: April 2016

Aus den Chinolin‐N‐oxiden (I) entstehen mit den Oxazolinonen (II) die Kondensationsprodukte (III).
ChemInform Abstract: STUDIES ON TERTIARY AMINE OXIDES. LXIX. REACTIONS OF 2‐CHLOROMETHYLQUINOLINE DERIVATIVES WITH 2‐NITROPROPANE
Authors: NISHIKAWA M. , SAEKI S. , HAMANA M. , NODA H.
Published: April 2016

Bei der Reaktion von 2‐Chlormethylchinolin (I) und seinen N‐Oxiden mit dem Na‐Salz von 2‐Nitropropan (II) entstehen über eine O‐Alkylierung Aldehyde, wie für die Verbindung (I) im Formelschema gezeigt ist.
ChemInform Abstract: A VERSATILE NEW SYNTHESIS OF QUINOLINES AND RELATED FUSED PYRIDINES. PART IV. SIMPLE ONE‐POT ROUTE TO PYRIDO(2,3‐B)QUINOLIN‐2‐ONES FROM ANILIDES
Authors: METH‐COHN O. , TARNOWSKI B.
Published: April 2016

Bei der Herstellung von 2‐Chlor‐3‐formyl‐chinolinen (IV) aus Acetaniliden unter Vilsmeier‐ Bedingungen entstehen als Nebenprodukte die Pyridochinolinone (V).
ChemInform Abstract: SYNTHESIS OF 4‐AMINO‐1H‐PYRROLO(2,3‐B)PYRIDINE (1,7‐DIDEAZAADENINE) AND 1H‐PYRROLO(2,3‐B)PYRIDIN‐4‐OL (1,7‐DIDEAZAHYPOXANTHINE)
Authors: SCHNELLER S. W. , LUO J.‐K.
Published: April 2016

Bei der Nitrierung des lH‐Pyrrolo(2,3‐b)pyridin‐7‐oxids (Ia) erhält man die Nitroverbindungen (Ib) und (II); letztere entsteht auch aus dem Brom‐Derivat (III) unter Substitution.
ChemInform Abstract: DERIVATIVES OF 1,2,3,3‐TETRAMETHYL‐2‐AZABICYCLO(2.2.2)OCTAN‐5‐TRANS‐OL WITH ANTIARRHYTHMIC AND OTHER ACTIVITIES. V
Authors: LONGOBARDI M. , BONDAVALLI F. , SCHENONE P. , RANISE A. , GIORDANO L. , PERNA D. , GIASI M. , ROSATTI F. , MARMO E.
Published: April 2016

Das aus dem Alkohol (I) mit Phosgen erhaltene Chlor‐carbonat (II) reagiert mit sekundären Aminen zu Urethanen (III).
ChemInform Abstract: MEDICINAL CHEMICAL STUDIES ON ANTIPLASMIN DRUGS. VII. OXA ANALOGS OF 4‐AMINOMETHYLCYCLOHEXANECARBOXYLIC ACID
Authors: ISODA S. , YAMAGUCHI H. , SATOH Y. , HIRATA M.
Published: April 2016

Es werden Synthesewege für die Oxaanaloga (II), (IV) und (VII) der 4‐Aminomethylcyclohexancarbonsäure (VIII) angegeben.
ChemInform Abstract: PYRIDO(2,3‐D)PYRIMIDINE ANTIBACTERIAL AGENTS. IV. SYNTHESIS OF METABOLITES OF F PIROMIDIC ACID
Authors: MATSUMOTO J. , MINAMIDA A. , KIMURA Y. , MINAMI S.
Published: April 2016

Drei Metaboliten (IIIa), (V) und (VIII) des Baktericids Piromidsäure (I) werden zur Absicherung ihrer Strukturen synthetisiert, da festgestellt worden war, daß das Abbauprodukt (IIIa), das im Blut und Harn von Menschen, die das Baktericid (I) eingenommen hatten, gefunden wurde, stärkere antibakterielle Wirkung zeigt als die Stammverbindung.
ChemInform Abstract: PHOSGENIMINIUM SALTS. PART 28. ANNELATION OF 5 OR 6 MEMBERED HETEROCYCLES TO URACIL DERIVATIVES VIA PHOSGENIMINIUM SALT CONDENSATION
Authors: KOKEL B. , LESPAGNOL C. , VIEHE H. G.
Published: April 2016

Das Phosgeniminiumsalz (II) kondensiert mit den Barbitursäuren (I) bzw. (IV) zu den neuen Amidchloriden (III) bzw. (V), die mit den Nucleophilen (VI) zu den entsprechenden Amiden oder Amidinen (VII) reagieren.
ChemInform Abstract: ALKYLATION OF ENAMINES OF BIS(ETHYLTHIO)ACETALDEHYDE: SYNTHESIS OF NORPYRENOPHORIN
Authors: BATES G. S. , RAMASWAMY S.
Published: April 2016

Ausgehend von Glyoxal (I) erhält man die Enamine (IV), deren Kaliumsalze alkyliert und anschließend zu den Thioacetaldehyden (VI) hydrolysiert werden.
ChemInform Abstract: SYNTHESIS OF DIETHYL, DI‐N‐OCTYL, AND MONO‐ AND DICYCLOHEXANO MACROCYCLIC POLYETHER‐DIESTER LIGANDS
Authors: JOLLEY S. T. , BRADSHAW J. S.
Published: April 2016

Aus den Polyethylenglykolen (III) entstehen mit 1‐Butenoxid (II) bzw. 1‐Decenoxid (IV) die entsprechenden Addukte (I) bzw. (V).
ChemInform Abstract: HOMOLOGATION OF ORGANOBORANES VIA CARBONYLATION‐REDUCTION
Authors: BROWN H. C. , FORD T. M. , HUBBARD J. L.
Published: April 2016

Bei der Behandlung mit CO und nachfolgender Lithiumalanat‐Reduktion erhält man aus den substituierten Organoboranen (I) die homologen Verbindungen (II) unter Einschjebung einer Methylengruppe.
ChemInform Abstract: HYDROBORATION. 56. CONVENIENT AND REGIOSPECIFIC ROUTE TO FUNCTIONALIZED ORGANOSILANES THROUGH THE HYDROBORATION OF ALKENYLSILANES
Authors: SODERQUIST J. A. , BROWN H. C.
Published: April 2016

Trimethylvinylsilan (I) liefert bei der Hydroborierung nach anschließender Oxidation die beiden isomeren Alkohole (III) und (IV).
ChemInform Abstract: SILICIUMHALTIGE HETEROCYCLISCHE VERBINDUNGEN. 37. MITT. DIREKTE SYNTHESE DES 9,9,10,10‐TETRACHLOR‐9,10‐DISILA‐9,10‐DIHYDRO‐ANTHRACENS AUS O‐DICHLORBENZOL
Authors: CHERNYSHEV E. A. , KOMALENKOVA N. G. , SHAMISHIN L. N. , TURETSKAYA R. A. , LUZGANOVA M. A.
Published: April 2016

Leitet man o‐Dichlorbenzo1(I) über einen Silicium‐Kupfer‐Kontakt (Cu‐Anteil 15‐40%), der noch Aktivatoren enthält, dann entsteht hauptsächlich das Tetrachlor‐disila‐anthracen (II).
ChemInform Abstract: REACTION OF ALIPHATIC ALCOHOLS WITH SULFUR AND RED PHOSPHORUS
Authors: MAZITOVA F. N. , KHAIRULLIN V. K.
Published: April 2016

Reaktionen niederer, mittlerer und höherer Alkohole (Ia) und (Ib), (Ic) und (Id) bzw. (Ie)‐(If) mit Schwefel und rotem Phosphor werden untersucht.
ChemInform Abstract: REACTIONS OF 1,5‐DIKETONES. XXXVIII. 8A‐HYDROXYPERHYDROPHOSPHINOLINES MADE FROM SEMICYCLIC 1,5‐DIKETONES AND PHOSPHINE
Authors: VYSOTSKII V. I. , KALINOV S. M. , TILICHENKO M. N.
Published: April 2016

Die Ketone (I) reagieren mit aus Magnesiumphosphid gewonnenem Phosphorwasserstoff zu 8a‐2‐Phenyl‐perhydro‐ phosphinolin‐1‐onen (IIa) bzw. entsprechenden Diphenylderivaten (IIb), die als Stereoisomerengemische anfallen.
ChemInform Abstract: REACTION OF BIS(DIALKYLAMIDO)CHLOROPHOSPHITES WITH IODINE
Authors: GORBATENKO ZH. K. , MITEL'MAN I. E. , FESHCHENKO N. G.
Published: April 2016

Methyliodid reagiert mit dem Phosphit (Ia) zum Phosphonium‐iodid (II) das sich zum Derivat (III) hydrolysieren läßt. Tris‐(dimethylamido)‐phosphit (IV) setzt sich mit Iodchlorid (VI) zum entsprechenden Phosphonium‐iodid (VII) um, das sich auch als Nebenprodukt bei der Reaktion zwischen dem Phosphit (Ia) und Iodmethan bildet.
ChemInform Abstract: REACTION OF CHLORAL WITH PHOSPHORUS‐CONTAINING IMINO ESTERS AND AMIDINES
Authors: PETROV K. A. , TIKHONOVA N. A. , BARANOV N. N. , YAKOVLEVA E. V.
Published: April 2016

Die Iminoester (I) liefern mit Ammoniumchlorid über die Chlorhydrate (II) phosphorylierte Amidine (III).
ChemInform Abstract: NOVEL SYNTHETIC ASPECTS OF THE PHOSPHONATE‐PHOSPHATE‐REARRANGEMENT. II. SYNTHESIS OF ENOLPHOSPHATES FROM 1‐OXOALKANPHOSPHONATES AND SULFUR YLIDES
Authors: HAMMERSCHMIDT F. , ZBIRAL E.
Published: April 2016

Die Acylphosphonate (I) reagieren mit dem Sulfoxoniummethylid (II) unter Bildung der Enolphosphate (IIIa) und (IIIb) sowie der Phosphonophosphate (IVa) und (IVC).
ChemInform Abstract: SYNTHESIS OF MONO‐ AND BISPHOSPHONIUM SALTS CONTAINING PHENYL AND HETEROCYCLIC NUCLEI IN PHOSPHORUS
Authors: BUKACHUK O. M. , MEGERA I. V. , SHEVCHUK M. I.
Published: April 2016

Bei der Umsetzung der 5‐Brom‐2‐furancarbonsäure (I) mit Triphenylphosphin (II) bei höherer Temperatur tritt Decarboxylierung zum Phosphoniumsalz (III) ein.
ChemInform Abstract: CONDENSATION OF SPIROPHOSPHORANES CONTAINING PHOSPHORUS‐HYDROGEN BOND WITH DIETHYL AZODICARBOXYLATE
Authors: FAUDUET H. , BURGADA R.
Published: April 2016

Spirophosphorane vom Typ (I), die bei 20°C mit ihren reaktiven trikoordinierten Tautomeren im Gleichgewicht stehen, reagieren mit dem Azodicarboxylat (II) zu den sehr reaktiven und daher instabilen Hydrazinen (III), die mit Me‐OH(analog mit ande‐ I/i? ren Alkoholen) als Derivate (IV) abgefangen werden; (IIIb) wird auch mit Ethylenglykol als Derivat (V) abgefangen.
ChemInform Abstract: PHOSPHORYLATION OF STERICALLY HINDERED PHENOLS BY PHOSPHORUS(III) DERIVATIVES
Authors: NIFANT'EV E. E. , PREDVODITELEV D. A. , TUSEEV A. P. , GRACHEV M. K. , ZOLOTOV M. A.
Published: April 2016

Aus den Phenolen (I) und Phosphortrichlorid entstehen die Dichlorphosphite (II).
ChemInform Abstract: HYDROCHLORINATION OF DIALKYL ESTERS OF 1,2‐ALKADIENEPHOSPHONIC ACIDS
Authors: MIKHAILOVA T. S. , ZAKHAROV V. I. , IGNAT'EV V. M. , IONIN B. I. , PETROV A. A.
Published: April 2016

1,2‐Alkadien‐phosphonsäure‐ester (I) mit einem tertiären C‐Atom in 3‐Stellung cyclisieren leicht durch HCl‐Gas zu Oxaphosphol‐3‐enen (II).
ChemInform Abstract: SOME PROPERTIES OF 2‐DIALKYLAMINO‐4,5‐BENZO‐1,3,2‐OXAZAPHOSPHOLANES
Authors: PUDOVIK M. A. , MIKHAILOV YU. A. , MALYKH T. A. , AL'FONSOV V. A. , ZAMALETDINOVA G. U. , BUTYEVA E. S. , PUDOVIK A. N.
Published: April 2016

o‐Aminophenol (III) reagiert mit Hexa‐ethyl‐triamido‐phosphit (II) zur Spiroverbindung (I) und mit den Dialkylamido‐dichlor‐phosphiten (IV) zu den Oxazaphospholanen (V)..Folgereaktionen des 2‐Diethyl‐4,5‐benzo‐l ,3,2‐oxazaphospholans z.B. mit Schwefel, Acrylnitril (VII) und Diethylamino‐trimethylsilan (X) werden untersucht.
ChemInform Abstract: REDUCTION OF PHOSPHORINANONES WITH FOUR‐COORDINATE PHOSPHORUS CONTAINING SELENOPHOSPHORYL AND PHOSPHORYL GROUPS
Authors: BOSYAKOV YU. G. , LOGUNOV A. P. , KRASNOMOLOVA L. P. , AGASHKIN O. V. , BUTIN B. M.
Published: April 2016

Die Reduktion der Phosphorinanone (I) und (IV) mit verschiedenen Reduktionsmitteln unter verschiedenen Reaktionsbedingungen wird untersucht.
ChemInform Abstract: TITANIUM METALLACARBENE‐METALLACYCLOBUTANE REACTIONS: STEPWISE METATHESIS
Authors: HOWARD T. R. , LEE J. B. , GRUBBS R. H.
Published: April 2016

Die Reaktion des für Olefinmetathesen erforderlichen Katalysators (I) mit den Olefinen (II) in THF in Gegenwart von 4‐Vinylpyridin‐Styrol‐Copolymeren als Lewisbase liefert die thermisch stabilen Produkte (III).
ChemInform Abstract: TRANSITION‐METAL COMPLEXES OF PYRROLE PIGMENTS. 16. COBALT COMPLEXES OF 1,19‐DIMETHYLDEHYDROCORRINS AS VITAMIN B12 MODELS
Authors: MURAKAMI Y. , AOYAMA Y. , TOKUNAGA K.
Published: April 2016

Die Co‐Komplexe eines l,19‐Dimethyl‐AD‐didehydrocorrins und seines Tetradehydro‐Analogen (I) und‐(ID, die beide gegenüber der Grundverbindung Corrin zusätzliche Doppelbindungen an peripheren Stellen und einen weiteren angularen Methylsubstituenten haben, wurden vom Standpunkt der Vitamin‐Blz‐Chemie aus untersucht.
ChemInform Abstract: PLATINUM COMPLEXES OF DIAMINOCARBOXYLATES AND THEIR ETHYL ESTER DERIVATIVES: ANTITUMOR ACTIVITY AND INTERACTION WITH DEOXYRIBONUCLEIC ACID
Authors: INAGAKI K. , KIDANI Y. , SUZUKI K. , TASHIRO T.
Published: April 2016

Ziel der Arbeit ist es zu klären, ob eine Ladung in Platinkomplexverbindungen verhindert, daß diese Verbindungen eine Antitumorwirkung zeigen, da bisher nur bei neutralen Pt‐Komplexen eine solche Wirkung gefunden wurde.
ChemInform Abstract: A CATIONIC ETHYLENE(HYDRIDO)IRIDIUM(III) COMPLEX
Authors: OLGEMOELLER B. + , BECK W.
Published: April 2016

Durch Einwirkung von Ethylen auf eine Suspension des Hydrido‐tetrafluoroborato‐Ir‐Komplexes (I) in CH2Cl2 konnte durch Ligandenaustausch der Titelkomplex (II) als Tetrafluoroborat isoliert werden.
ChemInform Abstract: STUDIES ON THE CONSTITUENTS OF OPHIOPOGONIS TUBERS. VII. SYNTHETIC STUDIES OF F HOMOISOFLAVONOIDS. (3)
Authors: TADA A. , SAITOH T. , SHOJI J.
Published: April 2016

Einige Homoisoflavonoide (IV), die aus der Knolle von Ophiopogon Japonicus isoliert worden waren, werden durch Kondensation des Acetophe‐ nons (I) mit dem Aldehyd (II) und anschließende Hydrierung und Ringschlußreaktion synthetisiert.
ChemInform Abstract: TOTAL SYNTHESIS OF (.+‐.)‐ZOAPATANOL
Authors: CHEN R. , ROWAND D. A.
Published: April 2016

Die Synthese der (aus Montanoa tomentosa isolierten) Titelverbindung (VIII) erfolgt ausgehend vom Trienol (I) sukzessiv über die Stufen (II), (IIIa), (IIIb), (IIIc), (Va), (Vb) und (VI).
ChemInform Abstract: STEREOCHEMISTRY OF DIHYDROPINOL AND 1,8‐CINEOL DERIVATIVES. PART V. PYROLYSIS S OF PHENYLURETHANES FROM THE DIHYDROPINOL AND CINEOL SYSTEMS
Authors: STARZEMSKA H. , PIATKOWSKI K.
Published: April 2016

Aus (‐)‐1‐Hydroxy‐ cis‐dihydropinol, (i)‐1‐Hydroxy‐cis‐2,3‐pinol, 8‐Hydroxy‐l ,4‐cineo1, (+)‐endo‐2‐Hy‐ droxy‐1 ,8‐cineol bzw. (i)‐exo‐2‐Hydroxy‐l ,8‐cineol werden mit Phenylisocyanat die Urethane (‐)‐(I), (i)‐(IV), (VI), (+)‐(IX) bzw. (t)‐(X) dargestellt und der Pyrolyse bei 220‐270°C unterworfen: Gebildet werden unter cis‐Eliminierung die Produkte (+)‐(II) und (+)‐(III), (+)‐(V), (VII) und (VIII), (+)‐(II) und (+)‐(III) bzw. (i)‐(XI) und (XII).
ChemInform Abstract: INHIBITORS OF STEROL BIOSYNTHESIS. SYNTHESIS OF 9α‐FLUORO‐3β‐HYDROXY‐5α‐CHOLEST‐8(14)‐EN‐15‐ONE AND RELATED COMPOUNDS
Authors: PARISH E. J. , SCHROEPFER G. J. JUN.
Published: April 2016

Aus den Cholestenonen (I) enstehen mit Orthoester die Enolether (II).
ChemInform Abstract: NEW SYNTHESIS OF STEROIDAL TETRAHYDROOXAZIN‐2‐ONES
Authors: SCHNEIDER G. , HACKLER L. , DOMBI G.
Published: April 2016

Die Aminomethyl‐ und Benzylaminomethyl‐Steroide (Ia) und (Ib) werden zu den Tetrahydrooxazinonen (I I) in ausgezeichneten Ausbeuten cyclisiert.
ChemInform Abstract: THALLIUM IN ORGANIC SYNTHESIS. 59. ALKALOID SYNTHESIS VIA INTRAMOLECULAR NONPHENOLIC OXIDATIVE COUPLING. PREPARATION OF (.+‐.)‐OCOTEINE, (.+‐.)‐ACETOXYOCOXYLONINE, (.+‐.)‐3‐METHOXY‐N‐ACETYLNORNANTENINE, (.+‐.)‐NEOLITSINE, (.+‐.)‐KREYSIGINE, (.+‐.)‐O‐METHYLKREYSIGINE, AND (.+‐.)‐MULTIFLORAMINE
Authors: TAYLOR E. C. , ANDRADE J. G. , RALL G. J. H. , MCKILLOP A.
Published: April 2016

Reaktion der Modellverbindungen (I) mit dem T1‐Reagenz (II) liefert die verbrückten Diarylsysteme (III).
ChemInform Abstract: A STEREOSPECIFIC SYNTHESIS OF NAPELLINE
Authors: SETHI S. P. , ATWAL K. S. , MARINI‐BETTOLO R. M. , TSAI T. Y. R. , WIESNER K.
Published: April 2016

Ausgehend von dem Phenol‐Derivat (I) wird nach angegebenem Schema stereospezitisch das "Denudatin"‐System (IVg) aufgebaut, das sich beim Erhitzen in Eisessig in das Napellin‐System (VI) umlagert.
ChemInform Abstract: ANALGESIC NARCOTIC ANTAGONISTS. 3. PREPARATION OF 7β‐METHYLDIHYDROTHEBAINE‐φ
Authors: LELAND D. L. , POLAZZI J. O. , KOTICK M. P.
Published: April 2016

Thebain (I) reagiert mit Lithiumdimethylcuprat zum Addukt (II) neben geringen Anteilen des Stereoisomeren (III).
ChemInform Abstract: VITAMIN D (CALCIFEROL) AND ITS ANALOGS. 19. REARRANGEMENT OF VINYLALLENES TO 1‐HYDROXYLATED VITAMIN D MODEL SYSTEMS LACKING THE D RING AND SIDE CHAIN
Authors: CONDRAN P. JUN. , OKAMURA W. H.
Published: April 2016

Aus Cyclohexanon entsteht mit Acetylen das Alkinol (I), das in bekannter Weise zum Bromallen (IIa) umgesetzt wird.
ChemInform Abstract: VITAMIN D (CALCIFEROL) AND ITS ANALOGS. 20. SYNTHESIS OF 3‐DEOXY‐3,3‐DIMETHYL‐1‐HYDROXYVITAMIN D3 FROM VINYLALLENE INTERMEDIATES AND RELATED THERMAL AND CONFIGURATIONAL STUDIES
Authors: MOURINO A. , LEWICKA‐PIEKUT S. , NORMAN A. W. , OKAMURA W. H.
Published: April 2016

Methyldimedon (I) wird mit Triphenyldiiodphosphor in das Vinyliodid (II) übergeführt, zu (IIIa) reduziert und zu (IIIb) silyliert.
ChemInform Abstract: NEW PROSTACYCLIN ANALOGS
Authors: BARTMANN W. , BECK G. , KNOLLE J. , RUPP R. H.
Published: April 2016

Ausgehend von dem geschützten Lacton (I) wird über die angegebenen Zwischenprodukte die Schlüsselverbindung (VIa) dargestellt und mit dem Bromester (VII) zu (VIIIa) kondensiert, aus dem nach A) der Lactimether (VIIIb) gewonnen wird.
ChemInform Abstract: REACTION OF 3‐FORMYLRIFAMYCIN SV WITH FORMALIN IN COMBINATION WITH PRIMARY ALKYLAMINES
Authors: TSUKAMOTO G. , TAGUCHI M. , AIKAWA N.
Published: April 2016

3‐Formylrifamycin SV (I) reagiert mit Formalin (II) und primären Alkylaminen (III) zu den Dihydropyrimidoderivaten (IV).
ChemInform Abstract: GENERAL STRATEGY FOR GIBBERELLIN SYNTHESIS: TOTAL SYNTHESES OF (.+‐.)‐GIBBERELLIN A1 AND GIBBERELLIC ACID
Authors: LOMBARDO L. , MANDER L. N. , TURNER J. V.
Published: April 2016

Die Synthese von (i)‐Gibberellin A1 (IX) erfolgt ausgehend vom Diendion (Ia) sukzessiv über die Stufen (Ib), (Ic), (IIa), (IIb), (IIIa) [daneben die epimere Säure (IIIb)] (IIIc), (IVa), (IVb), (Va), (Vb), (VIa), (VIb), (VIIa) [daneben das Epimere (VIII)], (VIIb) und (VIIc); die Synthese von Gibberellsäure (X) weiterhin wird ausgehend von (VIII) in zahlreichen Schritten durchgeführt (z.T.
A superior method for cell block preparation for fine‐needle aspiration biopsies
Authors: Balassanian Ronald , Wool Geoffrey D. , Ono Jill C. , Olejnik‐Nave Jolanta , Mah Molinda M. , Sweeney Brenda J. , Liberman Hava , Ljung Britt‐Marie , Pitman Martha B.
Published: April 2016

BACKGROUND

Cell block (CB) techniques for fine‐needle aspiration biopsies (FNABs) vary. A direct comparison of CB techniques with statistical validation was performed to identify the best method.

METHODS

Three CB techniques were compared: 1) FNAB rinsed in saline and clotted with plasma and thrombin (SPT); 2) FNAB rinsed in formalin and clotted with HistoGel (HG); and 3) FNAB rinsed in formalin, centrifuged, and the pellet captured in a collodion bag (ColB). FNAB was performed on 35 random surgical specimens for smears and each CB technique. A randomized blinded review of hematoxylin and eosin‐stained CB slides was performed and each case was scored on a scale of 1 to 3 for cellularity, preservation, and architecture and the overall best CB was identified. Significance was determined by the Mann‐Whitney U test for nonparametric ordinal data.

RESULTS

The mean cellularity score was 1.71 for SPT (standard deviation [SD], 0.89), 1.68 for HG (SD, 0.67), and 3.0 for ColB (SD, 0). The mean preservation score was 1.31 for SPT (SD, 0.58), 1.54 for HG (SD, 0.70), and 2.91 for ColB (SD, 0.37). The mean architecture score was 1.45 for SPT (SD, 0.70), 1.43 for HG (SD, 0.60), and 2.71 for ColB (SD, 0.57). There was no statistical significance noted between SPT or HG when compared for each category. ColB was found to be superior to both SPT and HG when compared for each category (P<.05). The overall best CB was obtained with ColB in 33 of 35 cases (94%), with SPT proving superior in 1 of 35 cases (3%) and HG superior in 1 of 35 cases (3%).

CONCLUSIONS

ColB appears to be a superior technique for CB, yielding greater cellularity, preservation, and architecture in the majority of cases. Cancer Cytopathol 2016;124:508–18. © 2016 American Cancer Society.
Participate in a comprehensive effort to create department emergency plans
Authors: Hope Joan
Published: April 2016

Are you ready to respond to an emergency in your academic unit? Does your department's emergency plan leave you confident you can react effectively to an active shooter? How about a suspicious package? Will essential functions continue smoothly if a natural disaster such as a hurricane or flood occurs?
Binder‐Free Electrodes of CoAl Layered Double Hydroxide on Carbon Fibers for All‐Solid‐State Flexible Yarn Supercapacitors
Authors: Jagadale Ajay D. , Guan Guoqing , Li Xiumin , Du Xiao , Ma Xuli , Hao Xiaogang , Abudula Abuliti
Published: April 2016

Yarn supercapacitors have received much attention because of their noticeable role in advanced technologies, such as microrobots, wearable electronic textiles, and implantable medical devices. They can be prepared with different carbon‐based materials, but many devices suffer from low energy densities. Conformally loaded, Faradaically active CoAl‐based layered double hydroxides (CoAl LDH) are loaded onto carbon fiber (CF) yarns to prepare supercapacitors with enhanced capacitance and energy density, avoiding the need for binding agents. The effect of different CoAl LDH loading amounts on morphological, structural, and electrochemical properties is studied, and a loading amount of 2.3 mg cm−2 is found to achieve the maximum specific capacitance of 634.3 F g−1 at a current density of 1 Ag−1. Flexible all‐solid‐state supercapacitor based on CoAl LDH@CF yarns offers excellent areal capacitance (195 mF cm−2) and volumetric energy density (1.6 mWh cm−3) with 94 % cyclic stability after 4000 galvanostatic charge–discharge (GCD) cycles. The energy density and flexibility of this CoAl LDH@CFs yarn‐based all‐solid‐state supercapacitor offer great potential for energy management in flexible electronics.
Modified technique of functional vertical hemilaryngectomy for cancer invading 1 hemicricoid
Authors: Guinchard Anne‐Claude , Monnier Philippe , Jaquet Yves , Monnier Yan , Ikonomidis Christos
Published: April 2016

Background

Partial laryngectomy techniques are challenging, especially in young patients where function has to be preserved without compromising the oncologic outcome. We present a modified laryngectomy technique indicated for tumors invading one hemicricoid.

Methods

Vertical hemilaryngectomy with reconstruction of neo‐glottis by hemi trachea and placement of an endolaryngeal silicon prosthesis for a 21‐y old female patient presenting with a synovial sarcoma located on the left arytenoid area.

Results

The prosthesis was removed at 6 w with tracheotomy closure at 8w post‐op. Patient underwent adjuvant radiotherapy. Functional outcome showed good swallowing without aspiration. Voice was hoarse. At 5 years post‐op the patient is free of recurrence presenting only mild dyspnea upon effort.

Conclusion

Vertical hemilaryngectomy including a hemicricoid is feasible with single stage reconstruction by a hemi‐trachea of 4 to 5 rings intussuscepted into the thyroid cartilage. The functional outcome is good considering oncologic safety and avoidance of a permanent tracheostomy. © 2016 Wiley Periodicals, Inc. Head Neck 38: 1708–1716, 2016
Glutathione antioxidant pathway activity and reserve determine toxicity and specificity of the biliary toxin biliatresone in zebrafish
Authors: Zhao Xiao , Lorent Kristin , Wilkins Benjamin J. , Marchione Dylan M. , Gillespie Kevin , Waisbourd‐Zinman Orith , So Juhoon , Koo Kyung Ah , Shin Donghun , Porter John R. , Wells Rebecca G. , Blair Ian , Pack Michael
Published: April 2016

Biliatresone is an electrophilic isoflavone isolated from Dysphania species plants that has been causatively linked to naturally occurring outbreaks of a biliary atresia (BA)‐like disease in livestock. Biliatresone has selective toxicity for extrahepatic cholangiocytes (EHCs) in zebrafish larvae. To better understand its mechanism of toxicity, we performed transcriptional profiling of liver cells isolated from zebrafish larvae at the earliest stage of biliatresone‐mediated biliary injury, with subsequent comparison of biliary and hepatocyte gene expression profiles. Transcripts encoded by genes involved in redox stress response, particularly those involved in glutathione (GSH) metabolism, were among the most prominently up‐regulated in both cholangiocytes and hepatocytes of biliatresone‐treated larvae. Consistent with these findings, hepatic GSH was depleted at the onset of biliary injury, and in situ mapping of the hepatic GSH redox potential using a redox‐sensitive green fluorescent protein biosensor showed that it was significantly more oxidized in EHCs both before and after treatment with biliatresone. Pharmacological and genetic manipulation of GSH redox homeostasis confirmed the importance of GSH in modulating biliatresone‐induced injury given that GSH depletion sensitized both EHCs and the otherwise resistant intrahepatic cholangiocytes to the toxin, whereas replenishing GSH level by N‐acetylcysteine administration or activation of nuclear factor erythroid 2‐like 2 (Nrf2), a transcriptional regulator of GSH synthesis, inhibited EHC injury. Conclusion: These findings strongly support redox stress as a critical contributing factor in biliatresone‐induced cholangiocyte injury, and suggest that variations in intrinsic stress responses underlie the susceptibility profile. Insufficient antioxidant capacity of EHCs may be critical to early pathogenesis of human BA. (Hepatology 2016;64:894‐907)
Beware of your Cre‐Ation: lacZ expression impairs neuronal integrity and hippocampus‐dependent memory
Authors: Reichel J.M. , Bedenk B.T. , Gassen N.C. , Hafner K. , Bura S.A. , Almeida‐Correa S. , Genewsky A. , Dedic N. , Giesert F. , Agarwal A. , Nave K.‐A. , Rein T. , Czisch M. , Deussing J.M. , Wotjak C.T.
Published: April 2016

Expression of the lacZ‐sequence is a widely used reporter‐tool to assess the transgenic and/or transfection efficacy of a target gene in mice. Once activated, lacZ is permanently expressed. However, protein accumulation is one of the hallmarks of neurodegenerative diseases. Furthermore, the protein product of the bacterial lacZ gene is ß‐galactosidase, an analog to the mammalian senescence‐associated ß‐galactosidase, a molecular marker for aging. Therefore we studied the behavioral, structural and molecular consequences of lacZ expression in distinct neuronal sub‐populations. lacZ expression in cortical glutamatergic neurons resulted in severe impairments in hippocampus‐dependent memory accompanied by marked structural alterations throughout the CNS. In contrast, GFP expression or the expression of the ChR2/YFP fusion product in the same cell populations did not result in either cognitive or structural deficits. GABAergic lacZ expression caused significantly decreased hyper‐arousal and mild cognitive deficits. Attenuated structural and behavioral consequences of lacZ expression could also be induced in adulthood, and lacZ transfection in neuronal cell cultures significantly decreased their viability. Our findings provide a strong caveat against the use of lacZ reporter mice for phenotyping studies and point to a particular sensitivity of the hippocampus formation to detrimental consequences of lacZ expression. © 2016 Wiley Periodicals, Inc.
Nevus count associations with pigmentary phenotype, histopathological melanoma characteristics and survival from melanoma
Authors: Taylor Nicholas J. , Thomas Nancy E. , Anton‐Culver Hoda , Armstrong Bruce K. , Begg Colin B. , Busam Klaus J. , Cust Anne E. , Dwyer Terence , From Lynn , Gallagher Richard P. , Gruber Stephen B. , Nishri Diane E. , Orlow Irene , Rosso Stefano , Venn Alison J. , Zanetti Roberto , Berwick Marianne , Kanetsky Peter A. ,   on behalf of the GEM Study Group
Published: April 2016

Although nevus count is an established risk factor for melanoma, relationships between nevus number and patient and tumor characteristics have not been well studied and the influence of nevus count on melanoma‐specific survival is equivocal. Using data from the Genes, Environment and Melanoma (GEM) study, a large population‐based study of primary cutaneous melanoma, we evaluated associations between number of nevi and patient features, including sun‐sensitivity summarized in a phenotypic index, and tumor characteristics. We also assessed the association of nevus count with melanoma‐specific survival. Higher nevus counts were independently and positively associated with male gender and younger age at diagnosis, and they were inversely associated with lentigo maligna histology. We observed a borderline significant trend of poorer melanoma‐specific survival with increasing quartile of nevus count, but little or no association between number of nevi and pigmentary phenotypic characteristics or prognostic tumor features.
Biodistribution of polyacrylic acid‐coated iron oxide nanoparticles is associated with proinflammatory activation and liver toxicity
Authors: Couto Diana , Freitas Marisa , Costa Vera Marisa , Chisté Renan Campos , Almeida Agostinho , Lopez‐Quintela M. Arturo , Rivas José , Freitas Paulo , Silva Paula , Carvalho Félix , Fernandes Eduarda
Published: April 2016

Iron oxide nanoparticles (IONs) have physical and chemical properties that render them useful for several new biomedical applications. Still, so far, in vivo safety studies of IONs with coatings of biomedical interest are still scarce. The aim of this study, therefore, was to clarify the acute biological effects of polyacrylic acid (PAA)‐coated IONs, by determining their biodistribution and their potential proinflammatory and toxic effects in CD‐1 mice. The biodistribution of PAA‐coated IONs in several organs (liver, spleen, kidneys, brain, heart, testes and lungs), the plasma cytokines, chemokine and aminotransferases levels, white blood cell count, oxidative stress parameters, adenosine triphosphate and histologic features of liver, spleen and kidneys were evaluated 24 h after a single acute (8, 20 or 50 mg kg−1) intravenous administration of PAA‐coated IONs in magnetite form. The obtained results showed that these IONs accumulate mainly in the liver and spleen and, to a lesser extent, in the lungs. Although our data showed that PAA‐coated IONs do not cause severe organ damage, an inflammatory process was triggered in vivo, as evidenced by as evidenced by increased neutrophils and large lymphocytes in the differential blood count. Moreover, an accumulation of iron in macrophages of the liver and spleen was observed and hepatic lipid peroxidation was elicited, showing that the IONs are able to induce oxidative stress. The effects of these nanoparticles need to be further investigated regarding the mechanisms involved and the long‐term consequences of intravenous administration of PAA‐coated IONs. Copyright © 2016 John Wiley & Sons, Ltd.
Construction of a patterned hydrogel—fibrous mat bilayer structure to mimic choroid and Bruch's membrane layers of retina
Authors: Komez Aylin , Baran Erkan T. , Erdem Uzeyir , Hasirci Nesrin , Hasirci Vasif
Published: April 2016

Deterioration of retina and death of the retinal cells due to age, diabetes, or occlusion can cause retinal degeneration which leads to loss of vision. In this study, it is aimed to design a bilayered matrix to mimic the choroid and the Bruch's membrane of the retinal tissue. As choroid, a microchanneled network resembling a fractal tree design was fabricated by photolithography over photo‐cross‐linkable methacrylated hyaluronic acid hydrogel. Gelatin or collagen was immobilized into the microchannels to enhance adherence of Human Umbilical Vein Endothelial Cells (HUVEC). At late culture periods (2 weeks), formation of tubular structures due to proliferation of the attached cells was observed. As Bruch's membrane, an electrospun fibroin nanofiber mat was produced to grow retinal pigment epithelium (RPE) cells on. Cellular interactions between RPE and HUVEC in the microchannels were investigated in a coculture model in a noncontact mode. It was deduced that by combining the RPE layer on the highly permeable Bruch's membrane with the choroid layer populated by HUVECs, a retinal substitute which might have a potential for use in the treatment of retinal diseases is possible. © 2016 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 104A: 2166–2177, 2016.
Novel grooved substrata stimulate macrophage fusion, CCL2 and MMP‐9 secretion
Authors: Moon Haisle , Cremmel Clément V. M. , Kulpa Alina , Jaeger Nicolas A. F. , Kappelhoff Reinhild , Overall Christopher M. , Waterfield J. Douglas , Brunette Donald M.
Published: April 2016

Rough surface topographies on implants attract macrophages but the influence of topography on macrophage fusion to produce multinucleated giant cells (MGC) and foreign body giant cells (FBGC) is unclear. Two rough novel grooved substrata, G1 and G2, fabricated by anisotropic etching of Silicon <110> crystals without the use of photolithographic patterning, and a control smooth surface (Pol) were produced and replicated in epoxy. The surfaces were compared for their effects on RAW264.7 macrophage morphology, gene expression, cyto/chemokine secretion, and fusion for one and five days. Macrophages on grooved surfaces exhibited an elongated morphology similar to M2 macrophages and increased cell alignment with surface directionality, roughness and cell culture time. Up‐regulated expression of macrophage chemoattractants at gene and protein level was observed on both grooved surfaces relative to Pol. Grooved surfaces showed time‐dependent increase in soluble mediators involved in cell fusion, CCL2 and MMP‐9, and an increased proportion of multinucleated cells at Day 5. Collectively, this study demonstrated that a rough surface with surface directionality produced changes in macrophage shape and macrophage attractant chemokines and soluble mediators involved in cell fusion. Thesein vitroresults suggest a possible explanation for the observed accumulation of macrophages and MGCs on rough surfaced implantsin vivo. © 2016 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 104A: 2243–2254, 2016.
Performance analysis of exponential‐fed perfusion cultures for pDNA vaccines production
Authors: García‐Rendón Aurora , Munguía‐Soto Rodolfo , Montesinos‐Cisneros Rosa M. , Guzman Roberto , Tejeda‐Mansir Armando
Published: April 2016

BACKGROUND

The clinical application of plasmid DNA (pDNA) vaccines is progressing and it is essential to develop industrial bioprocesses to economically manufacture these macromolecules. In order to contribute to achieving this goal, in this work an exponential‐fed perfusion (EFP) culture for the production of pVAX1‐NH36 hosted in Escherichia coli DH5α for application as specific vaccine was investigated using a theoretical–experimental approach.

RESULTS

An experimental plasmid productivity of 3.0 mg L−1 h−1 was obtained, which represent a 1.5‐fold increase in this performance criteria. A mathematical model to investigate the system performance was built and validated. A novel aspect of the study is the analysis of the influence of individual model parameters on selected output variables and on scale‐up.

CONCLUSIONS

This work contributes to the design and optimization of EFP cultures for the efficient production of pDNA for therapeutic use. The higher productivity of the EFP bioprocess might reduce both capital investment and operational costs and as a result be economically attractive compared with conventional bioprocess. © 2016 Society of Chemical Industry