Chougala Bahubali M, Samundeeswari S, Holiyachi Megharaja, Shastri Lokesh A, Dodamani Suneel, Jalalpure Sunil, Dixit Sheshagiri R, Joshi Shrinivas D, Sunagar Vinay A
Department of Chemistry, Karnatak University, Dharwad, 580003, Karnataka, India.
Department of Chemistry, Karnatak University, Dharwad, 580003, Karnataka, India.
Eur J Med Chem. 2017 Jan 5;125:101-116. doi: 10.1016/j.ejmech.2016.09.021. Epub 2016 Sep 13.
A green, eco-friendly and efficient protocol has been developed and synthesized a series of coumarin based pyrano[2,3-c]pyrazole derivatives (3) by multi-component reaction (MCR). Unexpected 3-coumarinyl-3-pyrazolylpropanoic acids (4) have been isolated by the reaction of compound (3) in acidic conditions. Further, intramolecular cyclization of compounds (4) leads to CC chromons (9) and these compounds were screened for their biological activities using array of techniques. Most of the compounds exhibited promising antibacterial activity, in particular Gram-positive bacteria. The anti-inflammatory assay was evaluated against protein denaturation as well as HRBC membrane stabilization methods and compounds exhibit excellent anti-inflammatory activity in both methods. Molecular docking study has been performed for all the synthesized compounds with S. aureus dihydropteroate synthetase (DHPS) and results obtained are quite promising.
已开发出一种绿色、环保且高效的方案,通过多组分反应(MCR)合成了一系列基于香豆素的吡喃并[2,3-c]吡唑衍生物(3)。在酸性条件下,通过化合物(3)的反应分离出了意外的3-香豆素基-3-吡唑基丙酸(4)。此外,化合物(4)的分子内环化导致CC色酮(9),并使用一系列技术对这些化合物的生物活性进行了筛选。大多数化合物表现出有前景的抗菌活性,特别是对革兰氏阳性菌。针对蛋白质变性以及HRBC膜稳定化方法评估了抗炎活性,并且化合物在这两种方法中均表现出优异的抗炎活性。对所有合成化合物与金黄色葡萄球菌二氢蝶酸合酶(DHPS)进行了分子对接研究,获得的结果很有前景。