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Synthesis, antitubercular activity and molecular docking study of substituted [1,3]dioxino[4,5-d]pyrimidine derivatives via facile CAN catalyzed Biginelli reaction
Nucleosides, Nucleotides & Nucleic Acids ( IF 1.3 ) Pub Date : 2021-09-02 , DOI: 10.1080/15257770.2021.1972310
Talavara Venkatesh 1 , Yadav D Bodke 1 , B Manjunatha 1 , S Ravi Kumar 2
Affiliation  

Abstract

We have developed a simple and convenient method for the synthesis of substituted-aryllidine-2,2-dimethyl-7-thioxo/oxo-4H-[1,3]dioxino[4,5-d]pyrimidine derivatives (4a-g) via one-pot Biginelli reaction of Meldrum’s acid (1), indole-3-carbaldehyde/thiophene-2-carbaldehyde/2-chloro-quinoline-3-carbaldehyde (2) and amines (3) in aqueous ethanol in the presence of a catalytic amount of CAN. The obtained pyrimidine hybrids were screened for their antimycobacterial activity against Mycobacterium tuberculi H37RV strain. The antimycobacterial results showed that compounds 4a and 4b exhibited excellent activity with MIC value of 1.6 µg/mL, four-fold greater than the standard streptomycin (6.24 µg/mL), while compounds (4c-g) showed lower efficacy. To study the interaction between the synthesized compounds and receptor, the compounds 4a, 4b, 4c, and 4d were studied for molecular docking on the enzyme enoyl-acyl carrier protein reductase (enoyl-ACP reductase) and the compounds 4a and 4b have emerged as active antitubercular agents with least binding energy –9.4 kcal/mol and −9.3 kcal/mol respectively.



中文翻译:

CAN催化Biginelli反应取代[1,3]二恶英[4,5-d]嘧啶衍生物的合成、抗结核活性及分子对接研究

摘要

我们开发了一种简单方便的方法来合成取代的芳基烷-2,2-二甲基-7-硫代/氧代-4H-[1,3]二恶英[4,5-d]嘧啶衍生物( 4a-g )通过 Meldrum 酸 ( 1 )、吲哚-3-甲醛/噻吩-2-甲醛/2-氯喹啉-3-甲醛 ( 2 ) 和胺类 ( 3 ) 在乙醇水溶液中的一锅 Biginelli 反应。CAN的催化量。筛选获得的嘧啶杂合体对结核分枝杆菌H 37 RV 菌株的抗分枝杆菌活性。抗分枝杆菌结果表明,化合物4a4b表现出优异的活性,MIC 值为 1.6 µg/mL,是标准链霉素 (6.24 µg/mL) 的四倍,而化合物 ( 4c-g ) 的功效较低。为研究合成的化合物与受体之间的相互作用,研究了化合物4a、4b、4c4d与酶烯酰-酰基载体蛋白还原酶 (enoyl-ACP reductase) 的分子对接,化合物4a4b已出现为结合能最低的活性抗结核药物分别为 –9.4 kcal/mol 和 -9.3 kcal/mol。

更新日期:2021-09-21
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