Department of Post-Graduate Studies and Research in Chemistry, Gulbarga University, Gulbarga 585 106, Karnataka, India.
Bioorg Med Chem Lett. 2013 Apr 1;23(7):1978-84. doi: 10.1016/j.bmcl.2013.02.036. Epub 2013 Feb 16.
As a part of systematic investigation of synthesis and biological activities of indole analogues linked to various heterocyclic systems, we have synthesized new compounds viz., 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitriles (2a-i), 4,5-diamino-6-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-8-aryl-2-oxo-2,6-dihydrodipyrano [2,3-b:3,2-e]pyridine-3-carbonitriles (3a-i), 4-amino-5-(5'-substituted 2'-phenyl-1H-indol-3-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-ones (4a-i), 4-amino-5-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-thiones (5a-i), 4-(5'-subtituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-1,4-dihydropyrano[2,3-c]pyrazol-3-amines (6a-i) and 5-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-7-aryl-3H-pyrano[2,3-d]pyrimidin-4(5H)-ones (7a-i). Antibacterial activity results revealed that, compound 6a showed promising activity versus Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 6d exhibited good activity against S. aureus, K. pneumoniae and Pseudomonas aeruginosa. Antifungal activity results indicated that, compound 4d exhibited maximum zone of inhibition against Aspergillus oryzae and Aspergillus flavus. In case of antioxidant activity, compound 4a showed promising radical scavenging activity, ferric ions (Fe(3+)) reducing antioxidant power (FRAP) and metal chelating activity.
作为系统研究连接各种杂环系统的吲哚类似物的合成和生物活性的一部分，我们合成了新的化合物，即 2-氨基-4-(5'-取代的 2'-苯基-1H-吲哚-3'-基)-6-芳基-4H-吡喃-3-甲腈 (2a-i)、4,5-二氨基-6-(5'-取代的 2'-苯基-1H-吲哚-3'-基)-8-芳基-2-氧代-2,6-二氢二吡喃并[2,3-b:3,2-e]吡啶-3-甲腈 (3a-i)、4-氨基-5-(5'-取代的 2'-苯基-1H-吲哚-3'-基)-7-芳基-1H-吡喃并[2,3-d]嘧啶-2(5H)-酮 (4a-i)、4-氨基-5-(5'-取代的 2'-苯基-1H-吲哚-3'-基)-7-芳基-1H-吡喃并[2,3-d]嘧啶-2(5H)-硫酮 (5a-i)、4-(5'-取代的 2'-苯基-1H-吲哚-3'-基)-6-芳基-1,4-二氢吡喃并[2,3-c]吡唑-3-胺 (6a-i) 和 5-(5'-取代的 2'-苯基-1H-吲哚-3'-基)-7-芳基-3H-吡喃并[2,3-d]嘧啶-4(5H)-酮 (7a-i)。抗菌活性结果表明，化合物 6a 对大肠杆菌、金黄色葡萄球菌和肺炎克雷伯菌表现出有希望的活性。化合物 6d 对金黄色葡萄球菌、肺炎克雷伯菌和铜绿假单胞菌表现出良好的活性。抗真菌活性结果表明，化合物 4d 对米曲霉和黄曲霉表现出最大的抑菌圈。在抗氧化活性方面，化合物 4a 表现出有希望的自由基清除活性、铁离子 (Fe(3+)) 还原抗氧化能力 (FRAP) 和金属螯合活性。
