Sübstitüe grup bulunduran yeni aminokarbotiyol pirolidin bileşiklerinin sentezi, karakterizasyonu ve biyoaktivitelerinin incelenmesi

Abstract

Bu çalışmada, pirolidin türevi bileşiklerin çeşitli sübstitüe benzoilizotiyosiyanat bileşikleri ile tepkimesi sonucu yeni polisübstitüe aminokarbotiyol pirolidin türevi bileşikler sentezlenerek, antibakteriyel ve antifungal özellikleri incelendi.Arilaminokarbotiyol pirolidin türevi olarak; 1-benzoilaminokarbotiyol-2-fenil-5-(2-naftil)pirolidin-2,4-dikarboksilik asit dimetil ester (KP1), 1-benzoilaminokarbotiyol-2-metil-5-(2-naftil)pirolidin-2,4-dikarboksilik asit dimetil ester (KP2), 1-benzoilaminokarbotiyol-2-fenil-5-(4-metoksifenil)pirolidin-2,4-dikarboksilik asit dimetil ester (KP3), 1-benzoilaminokarbotiyol-2-benzil-5-(4-metoksifenil)pirolidin-2,4- dikarboksilik asit dimetil ester (KP4), 1-(3-klorobenzoilaminokarbotiyol)-2,5-difenilpirolidin-2,4-dikarboksilik asit dimetil ester (KP5), 1-(2,4-diklorbenzoilaminokarbotiyol)-2-fenil-5-(4-klorfenil)pirolidin-2,4-dikarboksilik asit dimetil ester (KP6) ve 1-(4-metoksibenzoilaminokarbotiyol)-2-fenil-5-(4-klorfenil)pirolidin-2,4-dikarboksilik asit dimetil ester (KP7) bileşikleri elde edildi.Elde edilen yeni bileşiklerin yapıları, NMR (Nükleer Magnetik Rezonans), FT-IR (Fourier Dönüşümlü İnfrared) spektroskopisi, MS(Kütle Spektrometresi) ve elementel analiz teknikleriyle aydınlatıldı. Bu bileşiklerden 1-(3-klorobenzoilaminokarbotiyol)-2,5-difenilpirolidin-2,4-dikarboksilik asit dimetil ester (KP5) bileşiğinin yapısı ve stereokimyası tek kristal X-ışını kırınımı tekniğiyle aydınlatıldı.Sentezlenen yeni aminokarbotiyol pirolidin türevi bileşiklerin Bacillus subtilis (ATCC 6633), Escherichia coli (ATCC 25923), Staphylococcus aureus (ATCC 25813) ve Pseudomonas aeroginosa (ATCC 25853) gibi çeşitli Gram(+) ve Gram(-) bakteriler ile antibakteriyal; Candida glabrata (ATCC 4322) ve Candida parapsilosis (ATCC 22019) gibi mayalar ile de antifungal aktiviteleri incelendi.Anahtar Kelimeler: Aminokarbotiyol, pirolidin, tiyoüre, antibakteriyal aktivite ve antifungal aktivite.

In this study, some novel higly substituted aminocarbothioyl pyrrolidine derivatives were prepared from various substituted pyrrolidine and benzoylisothiocyanate and screened for their antibacterial and antifungal activity.As the novel arylaminocarbothioyl pyrrolidines, 1-benzoylaminocarbothioyl-2-phenyl-5-(2-napthyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester (KP1), 1-benzoylaminocarbothioyl-2-methyl-5-(2-napthyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester (KP2), 1-benzoylaminocarbothioyl-2-phenyl-5-(4-methoxyphenyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester (KP3), 1-benzoylaminocarbothioyl-2-benzyl-5-(4-methoxyphenyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester (KP4), 1-(3-chlorobenzoylaminocarbothioyl)-2,5-diphenylpyrrolidine-2,4-dicarboxylic acid dimethyl ester (KP5), 1-(2,4-dichlorobenzoylaminocarbothioyl)-2-phenyl-5-(4-chlorophenyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester (KP6) and 1-(4-methoxybenzoylaminocarbothioyl)-2-phenyl-5-(4-chlorophenyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester (KP7) were reported.The prepared novel compounds were charecterised by 1H-NMR, 13C-NMR, FT-IR, MS and micro analyses. The structure and stereochemistry of 1-(3-chlorobenzoylaminocarbothioyl)-2,5-diphenylpyrrolidine-2,4-dicarboxylic acid dimethyl ester (KP5) was also confirmed by X-Ray single crystal structure analiysis.The synthesized novel higly substituted aminocarbothioyl pyrrolidine compounds were tested against the Gram (+) and Gram (-) bacteria such as Bacillus subtilis (ATCC 29212), Escherichia coli (ATCC 25923), Staphylococcus aureus (ATCC 25813) and Pseudomonas aeroginosa (ATCC 25853) and the yeasts such as Candida glabrata (ATCC 4322) and Candida parapsilosis (ATCC 22019).Keywords: Aminocarbothioyl, pyrrolidine, thiourea, antibacterial activity and antifungal activity.