bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthese neuer 7‐Benzofuranmethanamine als heterocyclische Analoga des Squalenepoxidasehemmers Butenafine
Authors: Stanetty Peter , Koller Herbert , Pürstinger Gerhard , Grubner Silvia 
Published: October 2006

AbstractAusgewählte Titelverbindungen (6a‐f, 7a‐d) wurden aus entspr. (2,3‐Dihydro‐)7‐Benzofurancarbonsäuren 1a‐f bzw. 2a‐d durch RedAlR‐Reduktion der Carboxamide 4a‐f und 5a‐d aufgebaut. Aus praktischen Erwägungen wurde für die Darstellung der 2,3‐Dihydro‐2‐methyl‐7‐benzofuranmethanamine 6h‐k mit variiertem N‐Substitutionsmuster die Alkylierung des N‐Methyl‐benzofuranmethanamins 6g mit den vorgefertigten Aralkylbromiden 9a‐d bevorzugt.
Ketomethylenebestatin: Synthesis and Aminopeptidase Inhibition
Authors: Herranz Rosario , Castro‐Pichel Julia , García‐López M. Teresa , Gómez‐Monterrey Isabel , Pérez Concepción , Vinuesa Soledad 
Published: October 2006

AbstractThe synthesis of (6R,5S,2RS)‐6‐amino‐5‐hydroxy‐2‐isobutyl‐4‐oxo‐7‐phenylheptanoic acid (9), a carbaanalogue of the aminopeptidase (AP) inhibitor bestatin (1) is described. This synthesis was carried out by a malonic ester alkylation with the suitably protected halomethyl ketone of (2S,3R)‐AHPBA.
Peroxide als Pflanzeninhaltsstoffe, 12. Mitt.: Peroxide vom Davanon‐Typ aus der Eberraute (Artemisia abrotanum) und ihre Darstellung
Authors: Rücker Gerhard , Manns Detlef , Wilbert Sibylle 
Published: October 2006

AbstractAus den oberirdischen Teilen der Eberraute (Artemisia abrotanum L., Asteraceae) wurden neben (+)‐Davanon (1) und Arteinculton (3) die bekannten Peroxyhalbketale 2, 5 und 7 isoliert. Als neue Peroxide vom Davanon‐Typ konnten Epi‐Arteinculton (4) und Spiro‐Arteinculton (6) durch dc Vergleich in der Pflanze nachgewiesen werden. Bei der Singulett‐Sauerstoff‐Oxidation von 1 werden 2, 3, 4, 5und 7 gebildet, bei der Triplett‐Sauerstoff‐Oxidation 2, 3, 5, 6, 7 und Hydroxy‐Davanon.
Antimykotische Wirkstoffe, 20. Mitt.: Bioisostere 6‐Arylpyrimidin‐Derivate
Authors: Kreutzberger Alfred , Burger Angelika 
Published: October 2006

AbstractDurch Kondensation vonN‐(2‐Hydroxyethyl)‐N‐methylguanidinsulfat (1) mit den 1‐Aryl‐substituierten β‐Diketonen4a‐eerhält man die bioisosteren 2‐[(2‐Hydroxyethyl)‐methylamino]‐6‐arylpyrimidine5a‐e. Die Verbindungen5a‐cbesitzen signifikante antimykotischein vitro‐ undin vivo‐Aktivitäten.
Conformational Studies of Hexahydro‐benzo[c]phenanthridine Alkaloids: Solid and Solution Conformations of Deoxycorynoline
Authors: Kamigauchi Miyoko , Miyamoto Yuko , Iwasa Kinuko , Takao Narao , Ishida Toshimasa , In Yasuko , Inoue Masatoshi 
Published: October 2006

AbstractThe conformation of (±)‐deoxycorynoline (4), which was derived from (±)‐corynoline (1), was investigated by X‐ray crystallographic analysis. The crystal structure of (±)‐4 exists in B/C „anti‐cis”︁ conjunction, half‐chair of ring B and twist‐half‐chair of ring C, and shows the same conformation as that of the parent alkaloid (±)‐1. Conformational analyses of CD spectra in solution suggested that (+)‐4, derived from (+)‐1, has essentially the same conformation as in the crystal state of (±)‐4. The CD spectrum of (+)‐4 shows a slight temp.‐dependence, whereas that of (+)‐1 shows no dependency under the same conditions.
Carvedilol Stereopharmacokinetics in Rats: Affinities to Blood Constituents and Tissues
Authors: Stahl Elke , Mutschler Ernst , Baumgartner Ulrich , Spahn‐Langguth Hildegard 
Published: October 2006

AbstractCarvedilol, a lipophilic β‐adrenoceptor antagonist with vasodilating activities, is characterized by a high as well as stereoselective metabolic clearance and distribution volume. Tissue distribution of carvedilol enantiomers and their conjugates were determined under steady‐state conditions in rats (p.o., 10 mg/kg, repetitive dosage; n = 5) and after single i.v. administration in control rats and rats with surgical portacaval shunt (pcs) (10 mg/kg; n = 3 each group). In addition, in vitro plasma protein binding was evaluated. ‐ The plasma protein binding of carvedilol in rats is > 98% for total plasma (tp) and > 96% for rat serum albumin (rsa) solution (4%), with enantioselectivity ratios of 1.53 (tp) and 1.27 (rsa). Significantly higher unbound fractions were observed in pcs rats, in part due to reduced protein concentrations. ‐ In contrast to plasma, where a preponderance of the R‐enantiomer with an S/R ratio of 0.6 was found, S‐carvedilol was predominant in all tissues (heart, liver, kidneys, lung, spleen, muscle, and adipose tissue), with S/R ratios of 1.3‐1.4 in most of these tissues and 2.3 in liver. This preferential tissue partitioning of S‐carvedilol was in accordance with its higher unbound fraction in plasma. Carvedilol accumulated predominantly in the highly perfused and/or eliminating organs liver, kidneys, and lung (tissue/plasma ratios; lung: S 76, R 34; liver: S 21, R 5; kidney: S 8, R 3). A similarly enantioselective distribution into the heart of control as well as pcs rats was observed, where the S‐enantiomer concentrations exceeded the plasma concentrations 7‐fold. Probably because of the impaired liver function in pcs rats with increased importance of the renal route, kidney concentrations were higher in these rats. The kidney/plasma ratio was elevated approximately 2‐fold for the parent compound (control: S 7, R 2; pcs: S 14, R 4) and 4‐fold for the R‐carvedilol conjugate (control: S 2, R 1; pcs: S 3, R 4).The conjugates of carvedilol were detectable in all organs, with significantly smaller concentrations than those of the aglycones and with varying stereoselectivities.
New NO‐Donors with Antithrombotic and Vasodilating Activities, II: 3‐Alkyl‐N‐nitroso‐5‐sydnone Imines
Authors: Rehse Klaus , Schleifer Klaus‐Jürgen , Ciborski Thomas , Bohn Helmut 
Published: October 2006

AbstractFifteen 3‐alkyl‐, four 3‐cycloalkyl‐N‐nitroso‐5‐sydnone imines and five 3‐alkyl‐N‐nitro‐5‐sydnone imines were synthesized and their ability to inhibit platelet aggregation induced by collagen (Born‐test) was studied in vitro. Dependent on the chemical structure, the IC50‐values for the inhibition of platelet aggregation were in the range of 0.2‐140 μmol/L. It is suggested that this scale reflects different binding properties of the nitrosimines with respect to the platelet membrane. Highest activities were observed for the 3‐hexyl (2f) and the 3‐cyclohexyl (2p) derivative. Three nitrimines (3e, 3f, 3i) also showed IC50 values below 10 μmol/L. For the nitrosimines 2a, 2f, and 2m antithrombotic activity was demonstrated in vivo. They inhibited laser induced arterial thrombosis in anesthetized rats up to 70% two h after oral administration. In conscious renal‐hypertensive dogs, the decrease in systolic blood pressure and left ventricular enddiastolic pressure suggests an antianginal activity of the compound 2a similar to that of molsidomine (M). The smoother onset and the longer duration of action of the new compound as compared to M could be a significant advantage of 2a in the therapy of angina pectoris.
Effects of Oxygen Radicals, Hydrogen Peroxide and Water‐soluble Singlet Oxygen Carriers on 5‐ and 12‐Lipoxygenase
Authors: Müller Klaus , Ziereis Klaus 
Published: October 2006

AbstractInhibition of 5‐lipoxygenase from bovine polymorphonuclear leukocytes and 12‐lipoxygenase from bovine platelets by active oxygen species has been studied. Oxygen radicals and hydrogen peroxide markedly inhibited 12‐lipoxygenase, whereas 5‐lipoxygenase activity was only moderately influenced. Singlet oxygen liberated from water‐soluble naphthalene endoperoxides was without effect.
New 4‐Amino‐7,8‐dimethoxy‐5h‐pyrimido[5,4‐b]indole Derivatives: Synthesis and Studies as Inhibitors of Phosphodiesterases
Authors: Monge Antonio , Martínez‐Crespo Francisco J. , Villanueva M. Aránzazu , Font María , Santiago Esteban , Mart Juan J. , de Irujo Ínez , Alberdi Elena , López‐Unzu M. José , Cenarruzabeitia Edurne , Castiella Elena , Frechillac Diana 
Published: October 2006

AbstractA series of 4‐amino‐7,8‐dimethoxy‐5h‐pyrimido[5,4‐b]indole derivatives has been synthesized. These compounds resemble carbazeram and other pyridazino compounds with activity in the cardiovascular system. Some of these new compounds possess inotropic activity (Table 2), with a complementary effect on the inhibition of different CGI‐PDE (Table 3). The most active compounds 5, 6d, and 7 also possess activity as vasodilators (Table 4). Some of these new compounds inhibit blood platelet aggregation induced by ADP and AA and are active as inhibitors of human platelet PDEs (Tables 5 and 6).
Cyclic Analogs of Chemotactic Formylpeptides, I.: Synthesis and Biological Activity of For‐Cys‐Leu‐Phe‐Cys‐OMe
Authors: Zecchini Giampiero Pagani , Paradisi Mario Paglialunga , Torrini Ines , Lucente Gino , Traniello Serena , Spisani Susanna 
Published: October 2006

AbstractBy using the side chain to side chain mode of cyclization the 14‐membered disulfide cyclopeptide (5) has been synthesized as conformationally constrained analog of the prototypical chemotactic tripeptide For‐Met‐Leu‐Phe‐OMe. Compound 5 is inactive towards human neutrophils. The lack of biological activity of cyclotetrapeptide 5 is discussed taking into account the backbone folding and the side chain topography.
1‐Aryl‐2‐amino/hydrazino‐4‐phenyl‐1,6‐dihydro‐1,3,5‐triazine‐6‐thione and Related Thiocarbamides/Thiosemicarbazides as Antithyroidal Agents
Authors: Prasad R. , Srivastava P. K. 
Published: October 2006

AbstractDifferent 1‐aryl‐2‐benzylmercapto‐4‐phenyl‐1,6‐dihydro‐1,3,5‐triazine‐6‐thiones have been synthesized by known methods. These triazines on treatment with ammonia/hydrazine hydrate afforded the corresponding 1‐aryl‐2‐amino/hydrazino‐4‐phenyl‐1,6‐dihydro‐1,3,5‐triazine‐6‐thiones which on treatment with arylisothiocyanates afforded the related thiocarbamides/thiosemicarbazides. Some of these compounds show appreciable antithyroidal activity.
Aqua[1‐(2,6‐dichloro‐4‐hydroxyphenyl)‐2‐phenylethylenediamine]sulfatoplatinum(II) Complexes with Variable Substituents in the 2‐Phenyl Ring, II: Correlation of Molecular Structure and Estrogenic Activity of Breast and Prostate Cancer Inhibiting [erythro‐1‐(2,6‐Dichloro‐4‐hydroxyphenyl)‐2‐(2‐halo‐4‐hydroxyphenyl)ethylenediamine]platinum(II) Complexes
Authors: Gust Ronald , Schönenberger Helmut , Klement Ulrich , Range Klaus‐Jürgen 
Published: October 2006

AbstractComplete three‐dimensional X‐ray crystal structure analyses of estrogenic [erythro‐1‐(2,6‐dichloro‐4‐hydroxyphenyl)‐2‐(2‐halo‐4‐hydroxyphenyl)ethylenediamine]diiodoplatinum(II) complexes (halo = fluoro:erythro 8‐Ptl2 and halo = chloro:erythro‐9‐PtI2) which were synthesized for application in breast and prostate cancer, have been carried out. 6239 as well as 6521 reflexes were measured and refined to an R‐value of 0.105 and 0.066, respectively. The molecules of erythro‐8‐PtI2 are displaced laterally from a possible Pt‐Pt‐axis separated, alternatingly, by Pt‐Pt‐distances of 3.62 Å and 6.27 Å. A comparable structure possesses erythro‐9‐PtI2 with Pt‐Pt‐distances of 3.59 Å and 6.32 Å.The ethylenediamine ligands of erythro‐8‐PtI2 and erythro‐9‐PtI2 are puckered and exist in half chair conformations. For both complexes the 2,6‐dichloro‐4‐hydroxyphenyl ring is equatorially arranged, while the 2‐halo‐4‐hydroxyphenyl ring is nearly perpendicular to the N‐Pt‐N plane. The O‐O‐distance between the phenolic oxygens amounts to 8.1 Å in erythro‐8‐PtI2 and to 7.8 Å in erythro‐9‐PtI2. Though these O‐O‐distances differ strongly from that (12.1 Å), which is considered to be necessary for the binding of an estrogen to its receptor, [1‐(2,6‐dichloro‐4‐hydroxyphenyl)‐2‐(2‐halo‐4‐hydroxyphenyl)ethylenediamine)]platinum(II) complexes show estrogenic effects which are, however, strongly reduced compared to that of therapeutically used estrogens like diethylstilbestrol. The relationship between molecular structure and estrogenicity as well as the significance of the latter for antitumor activity and untoward side effects are thoroughly discussed.
Frankfurt Shift, 2. Mitt.: Weitere Beiträge zur intramolekularen Umlagerung von N‐Oxiden tertiärer Cycloalkylamine zu Lactamen (Frankfurt Shift)
Authors: Oelschläger Herbert , Schmidt Wolfgang 
Published: October 2006

AbstractDie grundlegenden Kenntnisse über den Frankfurt Shift wurden erweitert durch Untersuchungen über den kinetischen Isotopieeffekt, ein Kontrollexperiment mit 18O2‐Atmosphäre und einen Shift‐Versuch mit 1‐(4‐Fluorbenzyl)‐piperidin‐N‐oxid (4). Außerdem konnte der Shift erstmalig auch im Ganztierversuch (Ratte) nachgewiesen werden.
Antineoplastic and Antiviral Activities of Podophyllotoxin Related Lignans
Authors: Gordaliza Marina , Castro María A. , García‐Grávalos María D. , Ruiz Pilar , Del Corral José M. Miguel , Feliciano Arturo San 
Published: October 2006

Abstract28 cyclolignans, most of them derived from podophyllotoxin, have been evaluated for their antineoplastic and antiviral activities. They were subjected to screening against P‐388 murine leukemia, A‐549 human lung carcinoma, and HT‐29 colon carcinoma, while antiviral assays were performed on herpes simplex virus type I infecting fibroblasts of monkey kidney (HSV/CV‐1) and on vesicular stomatitis virus infecting fibroblasts of hamster kidney (VSV/BHK). A number of substances were active in both groups of assays at concentrations below 1μM; deoxypodophyllotoxin (1) being the most potent compound in all cases.
Synthese und kombinierte H1‐/H2‐antagonistische Aktivität von Mepyramin‐, Pheniramin‐ und Cyclizin‐Derivaten mit Cyanoguanidin‐, Harnstoff‐ und Nitroethendiamin‐Partialstrukturen
Authors: Schulze Frank R. , Alisch Rudi A. , Buschauer Armin , Schunack Walter 
Published: October 2006

AbstractDurch die Verknüpfung typischer Partialstrukturen von H1 und H2‐Antagonisten über eine Cyanoguanidin‐, Harnstoff‐ oder Nitroethendiamin‐gruppe wurden Substanzen mit kombinierter H1‐/H2‐antihistaminischer Wirkung synthetisiert. Der Verlust des basischen Seitenketten‐Stickstoffs führt am H1‐Rezeptor des Meerschweinchenileums zu einem Abfall der Aktivität im Vergleich zu den betreffenden Referenzsubstanzen mit gleicher H1‐Partialstruktur. Am Meerschweinchenatrium (H2‐Rezeptormodell) erwiesen sich Verbindungen mit Mepyramin‐ und Cyclizinstrukturelement im Vergleich zu den Referenz‐H2‐Antagonisten (Tiotidin, Ranitidin, Lamtidin) ebenfalls als schwächer wirksam. Dagegen führt die Verknüpfung mit einem Pheniraminbaustein zu stark wirksamen H2‐Antagonisten, die bis zu 27fache Cimetidinaktivität erreichen.
Untersuchungen an 1,4‐Naphthochinonen, 23. Mitt.1): 2/3‐Halogen‐2/3‐nitrophenyljuglonderivate, Synthese und cytotoxische Eigenschaften
Authors: Wurm Gotthard , Gurka Hans‐Joachim 
Published: October 2006

Abstract1,4‐Naphthochinonderivate lassen sich durch oxidative Decarboxylierung von 2‐ und 4‐Nitrobenzoesäure radikalisch arylieren. Ausgehend von 2‐ bzw. 3‐Halogenjuglonderivaten entstehen die 4‐Nitrophenylverbindungen 10–13 in guten, die 2‐Nitroanalogen 14–17 in geringen Ausb. Alle Verbindungen sind unwirksam gegen Viren vom Typ HSV und HIV, ihre z.T. ausgeprägte Cytotoxizität ist abhängig vom Substitutionsmuster. Die 3‐Aryl‐ und o‐Nitroderivate sind aktiver als die analogen 2‐Aryl‐ und p‐Nitroverbindungen. Der Einfluß der Brom‐ bzw. Chlorsubstitution ist nur bei dem Verbindungspaar 12/13 bemerkenswert.
Proton Acid‐Catalysed Transformations of Estrogen Derivatives: New Results and Some Mechanistic Aspects of the Kober Colour Reaction
Authors: Pindur Ulf , Schall Thomas 
Published: October 2006

AbstractThe 3‐O‐methylated estrogen derivatives 1a‐d and α‐estradiol (1e) underwent sulfuric acid‐catalysed transformations to furnish the steroids 2–6. The processes involved in the reaction sequence are regioselective sulfonation and, above all, the Wagner‐Meerwein rearrangement of the methyl group at C‐13. With the objective of obtaining further information on the course of the Kober colour reaction of estrogens, some UV/VIS and ESR spectroscopic investigations were also carried out.
New NO‐Donors with Antithrombotic and Vasodilating Activities, VII: Z/E‐Isomerism in Thiazole‐ and 1,3,4‐Thiadiazole‐2‐nitrosimines
Authors: Rehse Klaus , Lüdtke Eberhard 
Published: October 2006

AbstractIn thiazole‐ (23 compounds) and 1,3,4‐thiadiazole‐2‐nitrosimines (20 compounds) Z/E‐isomers were described by 1H‐NMR‐spectroscopy. There is a mutual conversion of the isomers. The coalescence temp. (Tc) mostly is 310 K. In the thiazole series, however, for five compounds higher energy barriers are observed. This is due to substituents in 4‐position with electron withdrawing properties. The Tc is increased when the compounds are dissolved in water instead of DMSO. Hereby it is concluded that the isomers have Ze or Ee configuration. It is made probable that the low field signal for the substituent in 3‐position corresponds to the Ze‐isomer, which has a slight preference. The free enthalpy of rotation, calculated approximately, is between 56.0 (1m) and 73.7 kJ/mol (1r).
Synthesis and Biological Evaluation of Some Potential Antimalarials. Synthese und biologische Bewertung einiger potentieller Wirkstoffe gegen Malaria
Authors: Tsai Chang Swei , Shen Ai Yu 
Published: October 2006

AbstractMalaria chemotherapy has been well reviewed. Malarial parasites gaining resistance is the major problem in the treatment of the disease. Some strains are resistant not only to chloroquine but also to amodiaquine. Few new drugs are available or foreseen for the near future. The principal metabolite of cinchona alkaloids appears to be oxidized at C‐2. This may result in a loss of activity. Pinder and Burger suggested that a trifluoromethyl group will prevent this oxidation. So 2‐tribromomethyl‐6‐methoxy‐4‐(4‐hydroxy‐3‐pyrrolidinomethylanilino)quinoline (I) was synthesized as a potential biocide (Scheme 1).
Complexation of Hydrocortison with β‐Cyclodextrin and Hydroxypropyl‐β‐Cyclodextrin
Authors: Preiss Andrea , Mehnert Wolfgang , Frömming Karl‐Heinz 
Published: October 2006

AbstractHydrocortison (HC) forms water‐soluble inclusion compounds with β‐cyclodextrin (βCD) and hydroxypropyl‐β‐cyclodextrin (HPβCD), as proved by the equilibrium phase solubility diagrams and by 1H‐NMR spectroscopy. The solubility isotherm of the HC/βCD system is of the BS type, that of the HPβCD system of the AL type. The values of the complex stability constants are K = 4792 M−1 and 1739 M−1, respectively. 8 parallel preparations of solid HC/βCD complexes by coprecipitation resulted in a stoichiometric ratio of 0.49:1 which corresponds to a molar ratio of 1:2; the HC content is 13.2±0.2%. The ratio of the HC/HPßCD complex is 0.335 which equals a molar ratio of 1:3; the HC content is 8.6 ± 0.2%. The proof of inclusion formation was performed by X‐ray diffractometry and thermoanalytical procedures (DSC, TG, thermofractography). We cannot exclude that some of the HC molecules are not included in the HPßCD cavity.
Isochromanylpenicilline
Authors: Unterhalt Bernard , Nocon Birgit , Krebs Bernt , Läge Mechthild 
Published: October 2006

Abstract(R/S)‐Isochroman‐1‐carbonsäure (1) wird in ihre Enantiomere gespalten und ebenso wie diese mit 6‐Aminopenicillansäure zu den Titelverbindungen 2 umgesetzt. Die Wirkung der neuen Penicilline gegenüber grampositiven und gramnegativen Bakterien wird mit der von Benzylpenicillin verglichen.
Zur Reaktion von 3,5‐Bis(methylthio)‐1,2‐dithiolium‐Salzen mit CH‐aciden Verbindungen
Authors: Popp Xue‐Ping , Hartke Klaus 
Published: October 2006

AbstractDie 3,5‐Bis(methylthio)‐1,2‐dithiolium‐tetrafluoroborate3a‐ckondensieren in Gegenwart von Ethyl‐diisopropylamin mit Malondinitril zu den Thiophenen9a‐c, mit Cyanessigsäuremethylester zu den Thiophenen9d‐fsowie zu den 3‐Alkyliden‐1,2‐dithiolen10a‐cund mit Nitromethan zu den Thiophenen9g, 12sowie dem 3‐Alkyliden‐1,2‐dithiol10d. Die Selbstkondensation von3aergibt das Trithiapentalen13und das Isotrithiapentalen14.
New NO‐Donors with Antithrombotic and Vasodilating Activities, IX: Thiadiazole Nitrosimines
Authors: Rehse Klaus , Lüdtke Eberhard 
Published: October 2006

AbstractTwenty 1,3,4‐thiadiazole‐2‐nitrosimines and two 1,2,4‐thiadiazole‐5‐nitrosimines were synthesized and assayed in the Born‐test for their antiplatelet activity. Only two 1,3,4‐thiadiazoles inhibited the aggregation at IC50 < 10 μmol/L. In an in vivo thrombosis model only in arterioles a small inhibition of thrombus formation was observed. The poor test results correspond to a very high chemical stability of the titel nitrosimines.
Zur Acetylierung von Spironolacton, Canrenon und 2‐Methylencanrenon
Authors: Görlitzer Klaus , Moormann Peter , Pollow Kunhard , Schaffrath Michael 
Published: October 2006

AbstractBei der Umsetzung der Titelverbindungen mit Acetanhydrid und Acetylchlorid werden das 3,5‐Dien‐3‐yl‐acetat 2, die isomeren 2,4,6‐ und 3,5,7‐Trien‐3‐yl‐acetate 3 und 4 sowie das 2,4,6,8(14)‐Tetraen‐3‐yl‐acetat 7 erhalten. Hydrolyse von 7 liefert das 2α‐Methl‐8,14‐didehydro‐canrenon (9). 7 und 9 wurden auf ihre Bindungsfähigkeit gegenüber Hormon‐Rezeptoren sowie den Serumproteinen SHBG und CBG geprüft: Die Substanzen erwiesen sich als inaktiv.
Untersuchungen an 1,4‐Napthochinonen, 24. Mitt.: Zur Dehalogenierung von 2‐/3‐Halogen‐1,4‐naphthochinon‐derivaten
Authors: Wurm Gotthard , Duchstein Hans‐Jürgen 
Published: October 2006

AbstractWährend Bu3SnH ein effektives Reagenz zur Debromierung von 2‐Bromnaphthochinonen ist, erfolgt Cl‐Eliminierung bei Einsatz von 1c nur zu 30%. Mit Et3SiH ist überhaupt keine Dechlorierung zu erreichen, dafür entsehen mit den 5‐Acetoxyderivaten 1a/1d als Startkomponenten die cyclischen Acetale 3a–c als selektiv geschützte Juglonderivate. Die Bromverbindung 3a entsteht nur bei Temp. unterhalb 10°, bereits bei Raumptemp. tritt Br‐Eliminierung ein, wobei 3b aber nur in geringer Ausb. anfällt. Ein besonders geeignetes Reagenz zur Debromierung und damit Gewinnung der Naturstoffe Plumbagin (2a) und Isoplumbagin (2b) aus den Bromderivaten 1a–b ist Zink‐Silber‐Paar, Cl‐Eliminierung erfolgt aber wieder nur in Spuren.
Synthesis of the First Penicillin Derivatives with Medium‐Sized Lactam Ring and of Related Thiazolidines
Authors: Imming Peter 
Published: October 2006

AbstractThe novel concept of penicillin derivatives 4 with a medium‐sized instead of a β‐lactam ring is presented. Two synthetic paths were invented, resulting in the evaluation of the synthetic potential in the succinic, glutaric, and adipic acid series. A number of novel penicillin‐derived thiazolidines were prepared, notably the derivatives 16 and 22 with anellated 7‐ and 13‐membered lactam ring.
Synthesis and in Vitro Degradation of Testosterone‐Lipid Conjugates
Authors: Scriba Gerhard K. E. 
Published: October 2006

AbstractTestosterone‐lipid conjugates were obtained by covalent binding of the drug to 1,3‐dipalmitoylglycerol via succinic acid to 4‐(1,3‐dipalmitoyl‐2‐glyceryl)butyric acid and to 3‐palmitoyloxy‐2‐palmitoyloxymethylpropionic acid. In contrast to the corresponding bis‐deacyl derivatives, the lipids were not significantly hydrolyzed in aqueous buffers and in plasma. Incubation with pancreatic lipase yielded primarily the bis‐deacyl compounds, which are comparable to monoglycerides, and subsequently slowly liberated testosterone. It is concluded that the lipid conjugates are substrates for pancreatic lipase. However, the drug was released very slowly due to steric hindrance.
Studien zur Chemie von thienoanellierten O,N‐ und S,N‐haltigen Heterocyclen, 9. Mitt.: Synthese und Calciumkanal blockierende Wirkung eines thienoanalogen KT‐362
Authors: Erker Thomas 
Published: October 2006

AbstractAusgehend vom Ester 5 wird über mehrere Stufen 4‐[3‐[2‐(3,4‐Dimethoxyphenyl)‐ethylamino]‐propanoyl]‐2‐ethyl‐4,5,6,7‐tetrahydrothieno[2,3‐b]‐[1,4]thiazepin (3) aufgebaut, eine thienoanaloge Verbindung zum Calciumkanalblocker KT‐362. Es wird über die Ca2+‐antagonistische Wirkung dieses Thiazepinderivats berichtet.