In this study, a novel series of 4-methyl-N-[2,7,8-(non)substituted)-3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl]benzene-1-sulfonamides (3a-g, 4), bearing benzenesulfonamide and spirothiazolidinone scaffolds, have been synthesized. The target compounds were prepared in two steps starting from the p-toluenesulfonyl hydrazide (1). The 4-methyl-N-[3,4-(non)substitutedcyclohexylidene]benzene-1-sulfono hydrazide derivatives (2a-g), which were used as intermediate products, were obtained from the reaction of p-toluenesulfonyl hydrazide (1) with appropriate cyclic ketones. The spirothiazolidinone compounds (3a-g, 4) were synthesized by the cyclization of the intermediate hydrazones (2a-g) with thioglycolic acid/thiolactic acid. Compounds 3a-g and 4 were characterized by elemental analysis, UV, IR, 1H-NMR, 13C-NMR (APT), HSQC, HMBC and ESI-MS spectroscopic methods and their structures were confirmed. The antibacterial and antifungal activity of the new spirothiazolidinone compounds (3a-g, 4) were screened in vitro against Staphylococcus aureus ATCC 29213, Staphylococcus epidermidis ATCC 12228, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 27853, Proteus mirabilis ATCC 14153, Candida albicans ATCC 1023, Candida. parapsilosis ATCC 22019 and Candida tropicalis ATCC 750. Their antimycobacterial activity was also tested in vitro against M. tuberculosis H37Rv ATCC 27294 (drug-sensitive strain), M. tuberculosis H37Rv ATCC 35822 (isoniazid-resistant strain), M. tuberculosis (isoniazid and rifampin-resistant strain, clinical isolate), M. tuberculosis (drug-sensitive strain, clinical isolate).

Bu çalışmada, benzensülfonamid ve spirotiyazolidinon yapısına sahip 4-metil-N-[2,7,8-(non)sübstitüe-3-okso-1-tiya-4-azaspiro[4.5]dek-4-il]benzen-1-sülfonamid (3a-g, 4) türevi bir seri yeni bileşik sentezlenmiştir. Hedef bileşiklerin sentezi p-toluensülfonil hidrazid (1) bileşiğinden başlayarak iki aşamada gerçekleştirilmiştir. p-Toluensülfonil hidrazid (1) bileşiğinin uygun siklik ketonlarla reaksiyona sokulmasıyla ara ürün olarak kullanılan 4-metil-N-[3,4-(non)sübstitüesikloheksiliden]benzen-1-sülfonohidrazidler (2a-g) elde edilmiştir. Hidrazon bileşiklerinin (2a-g) tiyoglikolik asit/tiyolaktik asit ile siklizasyonu sonucunda spirotiyazolidinon (3a-g, 4) bileşikleri sentezlenmiştir. Bileşiklerin yapı karakterizasyonu elementel analiz, UV, IR, 1H-NMR, 13C-NMR (APT), HSQC, HMBC ve ESI-MS spektroskopik yöntemleri ile gerçekleştirilmiş ve molekül yapıları doğrulanmıştır. Yeni spirotiyazolidinon bileşiklerinin (3a-g, 4) in vitro antibakteryel ve antifungal aktiviteleri Staphylococcus aureus ATCC 29213, Staphylococcus epidermidis ATCC 12228, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 27853, Proteus mirabilis ATCC 14153, Candida albicans ATCC 10231, Candida parapsilosis ATCC 22019 ve Candida tropicalis ATCC 750'ye karşı; antimikobakteryel aktiviteleri ise M. tuberculosis H37Rv ATCC 27294 (antitüberküloz ilaçlara duyarlı), M. tuberculosis H37Rv ATCC 35822 (isoniazide dirençli), çoklu ilaca dirençli M. tuberculosis (isoniazid ve rifampine dirençli hasta suşu), duyarlı M. tuberculosis'e (hasta suşu) karşı test edilmiştir.