Publication: Kumarin türevi yeni taç eter bileşiklerinin sentezi
Abstract
KUMARİN TÜREVİ YENİ TAÇ ETER BİLEŞİKLERİNİN SENTEZİ Kumarin (2H-1-benzopiran-2-on) bileşikleri, birçok bitki hücresinden ve mikroorganizmalardan izole edilen bileşikler olup laboratuarda da sentezlenebilmektedir. Kumarinler güzel kokularından dolayı parfümeri alanında; biyolojik aktivitelerinden dolayı da tıp alanında kullanılabilmektedir. Çok sayıda kumarin türevinin antikoagulan, sedatif, hipnotik etki,antibiyotik aktivite, östrojenik etki, HIV-1 proteazı inhibe etme özelliği, antiviral, spazmolitik etki gibi bir çok biyolojik aktiviteye sahip olduğu bilinmektedir. Yapılan bu çalışmada 7,8-dihidroksi-3-(3-metilfenil)kumarin ve 6,7-dihidroksi-3-(3-metilfenil)kumarin bileşikleri akrilonitrilleri üzerinden Knoevenagel Sentezi ile elde edildi. 7,8-dihidroksi-3-(3-metoksifenil)kumarin ise Perkin Reaksiyonu ile sentezlendi. Elde edilen kumarin türevleri metanolde kristallendirilerek saflaştırıldı. Hazırlanan bu kumarinlerin yeni 12-taç-4 ve 15-taç-5 polieter türevleri sentezlendi ve kolon kromotografisi ile saflaştırıldı. Ürünlerin yapıları IR, 1H-NMR ve kütle spektrumları ile aydınlatıldı. Ocak, 2003 Recai EKENEL
THE SYNTHESIS OF SOME NOVEL CROWN ETHER DERIVATIVES OF COUMARIN COMPOUNDS Cumarin, 2H-1-benzopyran-2-one, derivatives are constituents of many plants and microorganisims which can be isolated from their dried materials. Many of naturally-occurring coumarin derivatives can also be synthesized. Some coumarin compounds are known as the odoriferous principle of parfumes. In addition, many coumarin compounds have marked biological activities such as enzym inhibition, hypotoxicity, carcinogenecity, anticoagulant, sedative, hypnotic, HIV-1 protease inhibition, antiviral and antibiotic action in animals. In this study, we synthesized 7,8-dihydroxy-3-(3-methylphenyl)coumarin and 6,7-dihydroxy-3-(3-methylphenyl)coumarin via their acrilonitrile adopting Knoevenagel Synthesis. On the other hand 7,8-Dihydroxy-3-(3-methoxyphenyl) coumarin, was obtained adopting Perkin Reaction. All the obtained coumarin derivatives were purifed by chrystallization from methanol. The synthesis of novel 12-crown-4, 15-crown-5 derivatives of these coumarins were performed. The purification of crown compounds were made by using silica gel column chramotography. Finally, the structures of new coumarin-crown ethers were determined based on the results of spectroscopic methods such as 1H-NMR, IR and MS. Ocak, 2003Recai EKENEL
THE SYNTHESIS OF SOME NOVEL CROWN ETHER DERIVATIVES OF COUMARIN COMPOUNDS Cumarin, 2H-1-benzopyran-2-one, derivatives are constituents of many plants and microorganisims which can be isolated from their dried materials. Many of naturally-occurring coumarin derivatives can also be synthesized. Some coumarin compounds are known as the odoriferous principle of parfumes. In addition, many coumarin compounds have marked biological activities such as enzym inhibition, hypotoxicity, carcinogenecity, anticoagulant, sedative, hypnotic, HIV-1 protease inhibition, antiviral and antibiotic action in animals. In this study, we synthesized 7,8-dihydroxy-3-(3-methylphenyl)coumarin and 6,7-dihydroxy-3-(3-methylphenyl)coumarin via their acrilonitrile adopting Knoevenagel Synthesis. On the other hand 7,8-Dihydroxy-3-(3-methoxyphenyl) coumarin, was obtained adopting Perkin Reaction. All the obtained coumarin derivatives were purifed by chrystallization from methanol. The synthesis of novel 12-crown-4, 15-crown-5 derivatives of these coumarins were performed. The purification of crown compounds were made by using silica gel column chramotography. Finally, the structures of new coumarin-crown ethers were determined based on the results of spectroscopic methods such as 1H-NMR, IR and MS. Ocak, 2003Recai EKENEL