Küçükgüzel S Güniz, Oruç E Elçin, Rollas Sevim, Sahin Fikrettin, Ozbek Ahmet
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Marmara University, 81010 Haydarpasa, Istanbul, Turkey.
Eur J Med Chem. 2002 Mar;37(3):197-206. doi: 10.1016/s0223-5234(01)01326-5.
Two novel series of 4-thiazolidinone derivatives, namely 2-substituted-3-([4-(4-methoxybenzoylamino)benzoyl]amino)-4-thiazolidinones (7a-e) and 2-[4-(4-methoxybenzoylamino)benzoylhydrazono]-3-alkyl-4-thiazolidinones (5a-c) together with 2-[4-(4-methoxybenzoylamino)phenyl]-5-(substituted phenyl)amino-1,3,4-oxadiazoles (6a-c) have been synthesised as title compounds. N(1)-[4-(4-methoxybenzoylamino)benzoyl]-N(2)-substituted methylene hydrazines (3a-e) and 1-[4-(4-methoxybenzoylamino)benzoyl]-4-substituted phenyl thiosemicarbazides (4a-f) were also prepared and used as intermediate to give the title compounds. All synthesised compounds were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv and antimicrobial activities against various bacteria and fungi. Compounds 7a and 7b were found as the most active derivatives demonstrating 90 and 98% inhibition of mycobacterial growth of M. tuberculosis H37Rv in the primary screen at 6.25 microg mL(-1), respectively. However, level II assay revealed that the MIC values were not less than 6.25 microg mL(-1). None of the compounds showed significant antimicrobial activity against the microorganisms used whereas 3a and 7a inhibited the growth of several bacteria and fungi.
已经合成了两个新型的4-噻唑烷酮衍生物系列，即2-取代-3-([4-(4-甲氧基苯甲酰氨基)苯甲酰基]氨基)-4-噻唑烷酮(7a - e)和2-[4-(4-甲氧基苯甲酰氨基)苯甲酰肼基]-3-烷基-4-噻唑烷酮(5a - c)，以及2-[4-(4-甲氧基苯甲酰氨基)苯基]-5-(取代苯基)氨基-1,3,4-恶二唑(6a - c)作为目标化合物。还制备了N(1)-[4-(4-甲氧基苯甲酰氨基)苯甲酰基]-N(2)-取代亚甲基肼(3a - e)和1-[4-(4-甲氧基苯甲酰氨基)苯甲酰基]-4-取代苯基硫代氨基脲(4a - f)，并用作中间体来制备目标化合物。对所有合成的化合物进行了抗结核分枝杆菌H37Rv的抗分枝杆菌活性以及对各种细菌和真菌的抗菌活性筛选。在初次筛选中，发现化合物7a和7b是最具活性的衍生物，在6.25 μg mL(-1)时分别对结核分枝杆菌H37Rv的分枝杆菌生长有90%和98%的抑制作用。然而，二级试验表明最低抑菌浓度值不低于6.25 μg mL(-1)。没有一种化合物对所使用的微生物表现出显著的抗菌活性，而3a和7a抑制了几种细菌和真菌的生长。
