Reddy Cherkupally Sanjeeva, Rao Dasari Chandrashekar, Yakub Vookanti, Nagaraj Adki
Department of Chemistry, Kakatiya University.
Chem Pharm Bull (Tokyo). 2010 Jun;58(6):805-10. doi: 10.1248/cpb.58.805.
A new series of 3-(5-3-methyl-5-[(3-methyl-7-5-[2-(aryl)-4-oxo-1,3-thiazolan-3-yl]-1,3,4-thiadiazol-2-ylbenzo[b]furan-5-yl)methyl]benzo[b]furan-7-yl-1,3,4-thiadiazol-2-yl)-2-(aryl)-1,3-thiazolan-4-one 5a-j has been synthesized by the reaction of N2-[(E)-1-(4-methylphenyl)methylidene]-5-(3-methyl-5-[3-methyl-7-(5-[(E)-1-(4-methylphenyl)methylidene]amino-1,3,4-thiadiazol-2-yl)benzo[b]furan-5-yl]methylbenzo[b]furan-7-yl)-1,3,4-thiadiazol-2-amine 4a-j with thioglycolic acid. Chemical structures of all the new compounds were established by their IR, 1H-NMR, 13C-NMR, MS and elemental data. The 5a-j have been assayed for their nematicidal activity against Ditylenchus myceliophagus and Caenorhabditis elegans by aqueous in vitro screening technique. The screened data reveal that, the 5e is most effective against D. myceliophagus and C. elegans with 50% lethal dose (LD(50)) of 170 and 190 ppm, respectively and is almost equal to the activity of standard levamisole. The 5h and 5j are also most active against C. elegans with LD(50) of 200 ppm and D. myceliophagus with LD(50) of 190 ppm, respectively. Further, the 5a-j were screened for their antibacterial activity against three representative, Gram-positive bacteria viz. Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 6538p and Micrococcus luteus IFC 12708, and three Gram-negative bacteria viz. Proteus vulgaris ATCC 3851, Salmonella typhimurium ATCC 14028 and Escherichia coli ATCC 25922, and also screened for their antifungal activity against four fungal organisms viz. Candida albicans ATCC 10231, Aspergillus fumigatus HIC 6094, Trichophyton rubrum IFO 9185 and Trichophyton mentagrophytes IFO 40996. Most of these new compounds showed appreciable activity against the test bacteria and fungi, and emerged as potential molecules for further development.
通过N2-[(E)-1-(4-甲基苯基)亚甲基]-5-(3-甲基-5-[3-甲基-7-(5-[(E)-1-(4-甲基苯基)亚甲基]氨基-1,3,4-噻二唑-2-基)苯并[b]呋喃-5-基]甲基苯并[b]呋喃-7-基)-1,3,4-噻二唑-2-胺4a-j与巯基乙酸反应,合成了一系列新的3-(5-3-甲基-5-[(3-甲基-7-5-[2-(芳基)-4-氧代-1,3-噻唑烷-3-基]-1,3,4-噻二唑-2-基苯并[b]呋喃-5-基)甲基]苯并[b]呋喃-7-基-1,3,4-噻二唑-2-基)-2-(芳基)-1,3-噻唑烷-4-酮5a-j。通过红外光谱、1H-核磁共振、13C-核磁共振、质谱和元素数据确定了所有新化合物的化学结构。采用水相体外筛选技术测定了5a-j对食菌茎线虫和秀丽隐杆线虫的杀线虫活性。筛选数据表明,5e对食菌茎线虫和秀丽隐杆线虫最有效,50%致死剂量(LD(50))分别为170和190 ppm,几乎与标准左旋咪唑的活性相当。5h和5j对秀丽隐杆线虫的活性也最高,LD(50)为200 ppm,对食菌茎线虫的LD(50)为190 ppm。此外,还筛选了5a-j对三种代表性革兰氏阳性菌,即枯草芽孢杆菌ATCC 6633、金黄色葡萄球菌ATCC 6538p和藤黄微球菌IFC 12708,以及三种革兰氏阴性菌,即普通变形杆菌ATCC 3851、鼠伤寒沙门氏菌ATCC 14028和大肠杆菌ATCC 25922的抗菌活性,还筛选了它们对四种真菌,即白色念珠菌ATCC 10231、烟曲霉HIC 6094、红色毛癣菌IFO 9185和须癣毛癣菌IFO 40996的抗真菌活性。这些新化合物中的大多数对受试细菌和真菌表现出明显的活性,成为有进一步开发潜力的分子。