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2‐Amino‐3‐cyano‐4H‐chromene‐4‐ylphosphonates as potential antiviral agents: Synthesis, in ovo and in silico approach
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2020-09-20 , DOI: 10.1002/jhet.4154
Mahammad Sadik Shaik 1 , Maheshwara Reddy Nadiveedhi 1 , Mohan Gundluru 1, 2 , Ananda Kumar Reddy Narreddy 3 , Krishna Reddy Thathireddy 4 , Ranjani Ramakrishna 4 , Suresh Reddy Cirandur 1
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A simplistic synthetic procedure for the synthesis of structurally diversified 2‐amino‐3‐cyano‐4H‐chromene‐4‐ylphosphonates (4a‐j) were developed by the treatment of substituted salicylaldehydes, malononitrile, and dialkyl phosphite in presence of Cu(OAc)2 catalyst at room temperature and neat conditions. The synthesized compounds were tested for their antiviral assay. Among all, the compounds 4a, 4d and 4h have shown good in ovo antiviral activity against New castle disease virus (NDV) at a concentration of 150 μg/mL. The remarkable reduction in NDV virus population in embryos treated with title compounds (4a‐j) in a dose dependent manner, indicated that the synthesized compounds are extreme by toxic to the NDV virus. The title compounds were also docked against hemagglutinin neuraminidase enzyme and the more bioactive compound 4a showed highest docking score than the standard antiviral drug taribavirin while the compounds 4d and 4h has the same docking score as that of the standard.

中文翻译:

2-氨基-3-氰基-4H-色烯-4-基膦酸酯作为潜在的抗病毒剂:合成,卵内和计算机化方法

通过在Cu(OAc)存在下处理取代的水杨醛,丙二腈和亚磷酸二烷基酯,开发了一种结构简单的合成方法,用于合成结构多样的2-氨基-3-氰基-4-H-色烯-4-基膦酸酯(4a-j) )2催化剂在室温和纯净条件下。测试合成的化合物的抗病毒测定。其中,化合物4a4d4h在浓度为150μg/ mL时对新城疫病毒(NDV)表现出良好的卵内抗病毒活性。经标题化合物处理的胚胎中NDV病毒种群显着减少(4a-j)以剂量依赖的方式表明合成的化合物对NDV病毒具有极强的毒性。标题化合物也与血凝素神经氨酸酶对接,生物活性更高的化合物4a与标准抗病毒药物taribavirin相比具有最高的对接分数,而化合物4d4h与标准抗病毒药物对接分数相同。
更新日期:2020-09-20
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