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Green, unexpected synthesis of bis-coumarin derivatives as potent anti-bacterial and anti-inflammatory agents
European Journal of Medicinal Chemistry ( IF 6.7 ) Pub Date : 2017-10-28 , DOI: 10.1016/j.ejmech.2017.10.072
Bahubali M. Chougala , S. Samundeeswari , Megharaja Holiyachi , Nirmala S. Naik , Lokesh A. Shastri , Suneel Dodamani , Sunil Jalalpure , Sheshagiri R. Dixit , Shrinivas D. Joshi , Vinay A. Sunagar

A green and efficient protocol has been developed and a series of coumarin based pyrano[3,2-c]chromene derivatives (2) have been synthesized using multi-component reaction (MCR) approach. Unexpected 3-coumarinyl-3-pyrazolylpropanoic acids (3) and C4-C4 chromenes (5) have been isolated instead of expected product 4 by the reaction of compound (2) in formic acid at 90 °C for about 4–5 h and at 130 °C for about 8–10 h respectively. Further, C4-C4chromenes (5) formation was confirmed by intramolecular cyclization of compounds (3). These compounds were screened for their biological activities and most of them exhibited promising antibacterial activity. The anti-inflammatory assay was evaluated against HRBC membrane stabilization method and the compounds exhibit excellent anti-inflammatory activity. Molecular docking study has been performed for all the synthesized compounds with Klebsiella pneumoni aeacetolactate synthase and results obtained are quite promising.



中文翻译:

双香豆素衍生物的绿色,出乎意料的合成,可作为有效的抗菌和消炎剂

已开发出一种绿色高效的方案,并已使用多组分反应(MCR)方法合成了一系列基于香豆素的吡喃并[3,2- c ]色烯衍生物(2)。通过化合物(2)在90°C下于甲酸中反应约4–5,已分离出未预期的3-香豆基-3-吡唑基丙酸(3)和C 4 -C 4色烯(5),而不是预期的产物4。h和在130°C下分别进行约8–10 h。此外,通过化合物的分子内环化证实了C 4 -C 4色烯(5)的形成(3)。对这些化合物的生物学活性进行了筛选,其中大多数表现出有希望的抗菌活性。针对HRBC膜稳定方法评估了抗炎试验,该化合物具有出色的抗炎活性。已经用肺炎克雷伯菌乙酰乙酸合酶对所有合成的化合物进行了分子对接研究,并且获得的结果是很有希望的。

更新日期:2017-10-28
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