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1,3-二氢-2H-吲哚-2-酮衍生物:设计、合成、体外抗菌、抗真菌和抗结核研究。

1,3-Dihydro-2H-indol-2-ones derivatives: design, synthesis, in vitro antibacterial, antifungal and antitubercular study.

机构信息

Department of Pharmaceutical Chemistry, Ashok & Rita Patel Institute of Integrated Study and Research in Biotechnology and Allied Sciences (ARIBAS), New Vallabh vidyanagar, Gujarat 388121, India.

出版信息

Eur J Med Chem. 2011 Nov;46(11):5573-9. doi: 10.1016/j.ejmech.2011.09.023. Epub 2011 Sep 22.

Abstract

1,3-dihydro-2H-indol-2-ones derivatives are reported to exhibit a wide variety of biodynamic activities such as antituberculer, anti HIV, fungicidal, antibacterial, anticonvulsant. These valid observations led us to synthesize some new indole-2-one derivative. Thus, herein we report synthesis of various 5-substituted-3-[{5-(6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4 tetrahydro pyrimidin-5-yl)-1,3,4-thiadiazol-2-yl}imino]-1,3-dihydro-2H-indol-2-one derivatives 4a-l using one pot multicomponent-Biginelli reaction via CaCl(2) catalyst. Structures and purity of these compounds were confirmed by elemental, IR, ((1)H &(13)C) NMR and Mass spectral analysis. Newly synthesized compounds were also tested for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv, in vitro antibacterial activity against selected human pathogens viz. Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Staphylococcus aureus, Staphylococcus pyogenus, Bacillus subtilis and antifungal activity against Candida albicans, Aspergillus niger, Aspergillus clavatus strains.

摘要

1,3-二氢-2H-吲哚-2-酮衍生物被报道具有广泛的生物动力活性,如抗结核、抗 HIV、杀真菌、抗菌、抗惊厥。这些有效的观察结果促使我们合成了一些新的吲哚-2-酮衍生物。因此,在这里我们报告了使用 CaCl(2)催化剂通过一锅多组分 Biginelli 反应合成各种 5-取代-3-[(5-(6-甲基-2-氧代/硫代-4-苯基-1,2,3,4 四氢嘧啶-5-基)-1,3,4-噻二唑-2-基)亚氨基]-1,3-二氢-2H-吲哚-2-酮衍生物 4a-l。通过元素分析、红外光谱((1)H 和(13)C)NMR 和质谱分析确认了这些化合物的结构和纯度。还测试了新合成的化合物对结核分枝杆菌 H(37)Rv 的体外抗结核活性、对选定的人类病原体的体外抗菌活性,即大肠杆菌、铜绿假单胞菌、肺炎克雷伯菌、伤寒沙门氏菌、金黄色葡萄球菌、化脓性链球菌、枯草芽孢杆菌和抗真菌活性对白色念珠菌、黑曲霉、棒曲霉的活性。

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