Metil substitue azakalkonlar, n-alkil türevlerinin sentezi ve antimikrobiyal aktiviteleri
Methyl substituted azachalcones, the synthesis of n-alkyl derivatives and antimicrobial activities
Yazar: GÜLBİN MISIR
Danışman: PROF. DR. NURETTİN YAYLI
Karadeniz Teknik Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Bölümü / Kimya Ana Bilim Dalı / Organik Kimya Bilim Dalı
Derece: Yüksek Lisans, 2008
Konu: Kimya = Chemistry

Özet:
Bu çalışmada, iki kalkonoid benzeri azakalkon; (2E)-1-(4-metilfenil)-3-(3-piridil)-2-propen-1-on, 1 ve (2E)-1-(4-metilfenil)-3-(4-piridil)-2-propen-1-on, 2 Claisen-Schmidt reaksiyonuna göre sentezlendi.1 ve 2 nolu bileşiklerin N-alkil substitue türevleri alkillendirildi. Sentezlenen bileşikler; (2E)-1-(4-metilfenil)-3-(N-pentil-3-piridinyum bromür)-2-propen-1-on, 3, (2E)-1-(4-metilfenil)-3-(N-hekzil-3-piridinyum bromür)-2-propen-1-on, 4, (2E)-1-(4-metilfe-nil)-3-(N-heptil-3-piridinyum bromür)-2-propen-1-on, 5, (2E)-1-(4-metilfenil)-3-(N-oktil-3-piridinyum bromür)-2-propen-1-on, 6, (2E)-1-(4-metil-fenil)-3-(N-nonil-3-piridinyum bromür)-2-propen-1-on, 7, (2E)-1-(4-metilfenil)-3-(N-dekil-3-piridinyum bromür)-2-pro-pen-1-on, 8, (2E)-1-(4-metilfenil)-3-(N-undekil-3-piridinyum bromür)-2-propen-1-on, 9, (2E)-1-(4-metilfenil)-3-(N-dodekil-3-piridinyum bromür)-2-propen-1-on, 10, (2E)-1-(4-metilfenil)-3-(N-tetradekil-3-piridinyum bromür)-2-propen-1-on, 11, (2E)-1-(4-metilfenil)-3-(N-pentadekil-3-piridinyum bromür)-2-propen-1-on, 12, (2E)-1-(4-metilfenil)-3-(N-pen-til-4-piridinyum bromür)-2-propen-1-on, 13, (2E)-1-(4-metilfenil)-3-(N-hekzil-4-piridin-yum bromür)-2-propen-1-on, 14, (2E)-1-(4-metilfenil)-3-(N-heptil-4-piridinyum bromür)-2-propen-1-on, 15, (2E)-1-(4-metilfenil)-3-(N-oktil-4-piridinyum bromür)-2-propen-1-on, 16, (2E)-1-(4-metilfenil)-3-(N-nonil-4-piridinyum bromür)-2-propen-1-on, 17, (2E)-1-(4-metilfenil)-3-(N-dekil-4-piridinyum bromür)-2-propen-1-on, 18, (2E)-1-(4-metilfenil)-3-(N-undekil-4-piridinyum bromür)-2-propen-1-on, 19, (2E)-1-(4-metilfenil)-3-(N-dodekil-4-piridinyum bromür)-2-propen-1-on, 20, (2E)-1-(4-metilfenil)-3-(N-tetradekil-4-piridin-yum bromür)-2-propen-1-on, 21 ve (2E)-1-(4-metil-fenil)-3-(N-pentadekil-4-piridinyum bromür)-2-propen-1-on, 22'dir.Yapılan literatür araştırmaları sonucunda 1 ve 2 nolu bileşiklerin bilinen ve 3-22 nolu bileşiklerin yeni bileşikler oldukları tespit edildi. Sentezlenen bileşiklerin yapıları NMR, FT-IR ve UV teknikleriyle aydınlatıldı.Anahtar Kelimeler: Kalkonoid, Azakalkon, N-Alkillendirme, NMR

Abstract:
Methyl Substituted Azachalcones, Their Synthesis of N-AlkylDerivatives and Antimicrobial ActivitiesIn this work, 2 chalconoid-like azachalcones; (2E)-1-(4-methylphenyl)-3-(3-pyridyl)-2-propen-1-one, 1 and (2E)-1-(4-methylphenyl)-3-(4-pyridyl)-2-propen-1-one, 2 were synthesized according to the Claisen-Schmidt reaction.N-alkyl substituted derivatives of compounds 1 and 2 were synthesized. Synthesized compounds are (2E)-1-(4-methylphenyl)-3-(N-pentyl-3-pyridinum bromide)-2-propen-1-one, 3, (2E)-1-(4-methyl-phenyl)-3-(N-hexyl-3-pyridinum bromide)-2-propen-1-one, 4, (2E)-1-(4-methylphenyl)-3-(N-heptyl-3-pyridinum bromide)-2-propen-1-one, 5, (2E)-1-(4-methylphenyl)-3-(N-octyl-3-pyridinum bromide)-2-propen-1-one, 6, (2E)-1-(4-methylphe-nyl)-3-(N-nonyl-3-pyridinum bromide)-2-propen-1-one, 7, (2E)-1-(4-methylphenyl)-3-(N-decyl-3-pyridinum bromide)-2-propen-1-one, 8, (2E)-1-(4-methylphenyl)-3-(N-undecyl-3-pyridinum bromide)-2-propen-1-one, 9, (2E)-1-(4-methyl-phenyl)-3-(N-dodecyl-3-pyridi-num bromide)-2-propen-1-one, 10, (2E)-1-(4-methylphen-yl)-3-(N-tet-radecyl-3-pyridi-num bromide)-2-propen-1-one, 11, (2E)-1-(4-methylphenyl)-3-(N-penta-decyl-3-pyridi-num bromide)-2-propen-1-one, 12, (2E)-1-(4-methylphenyl)-3-(N-pentyl-4-pyridinum bro-mide)-2-propen-1-one, 13, (2E)-1-(4-methylphenyl)-3-(N-hexyl-4-pyridinum bromide)-2-propen-1-one, 14, (2E)-1-(4-met-hylphenyl)-3-(N-heptyl-4-pyridinum bromide)-2-propen-1-one, 15, (2E)-1-(4-methyl-phenyl)-3-(N-octyl-4-pyridinum bromide)-2-propen-1-one, 16, (2E)-1-(4-methylphenyl)-3-(N-nonyl-4-pyridinum bromide)-2-propen-1-one, 17, (2E)-1-(4-methylphenyl)-3-(N-decyl-4-pyridinum bromide)-2-propen-1-one, 18, (2E)-1-(4-met-hylphenyl)-3-(N-undecyl-4-pyridinum bromide)-2-propen-1-one, 19, (2E)-1-(4-methylphe-nyl)-3-(N-dodecyl-4-pyridinum bromide)-2-propen-1-one, 20, (2E)-1-(4-methylphenyl)-3-(N-tetradecyl-4-pyridinum bromide)-2-propen-1-one, 21 and (2E)-1-(4-methylphenyl)-3-(N-pentadecyl-4-pyridinum bromide)-2-propen-1-one, 22.Literature study showed that compounds 1 and 2 are known and compounds 3-22 are new compounds. The structures of the synthesized compounds were identified by NMR, FT-IR and UV spectra.Key Words : Chalconoid, Azachalcone, N-Alkylation, NMR