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Click chemistry‐inspired design, synthesis, and molecular docking studies of biscoumarin derivatives using carbon‐based acid catalyst
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2020-07-07 , DOI: 10.1002/jhet.4045
Dinesh K. Agarwal 1 , Ayushi Sethiya 2 , Pankaj Teli 2 , Anu Manhas 3 , Jay Soni 2 , Nusrat Sahiba 2 , Prakash C. Jha 4 , Shikha Agarwal 2 , Pradeep K. Goyal 1
Affiliation  

A green and eco‐benign synthesis of biscoumarin derivatives using carbon sulfonic acid, a solid support catalyst has been described. The reaction involved a one‐pot two‐component reaction of 4‐hydroxycoumarin and aldehyde using carbon sulfonic acid involving Knoevenegal‐Michael condensation. A series of aromatic (bearing electron withdrawing and releasing group) and heteroaromatic aldehydes has been converted to biscoumarins with excellent isolated yields. The reaction is in compliance with green principles, that is, inexpensive catalyst, easy to prepare, nontoxic, easy handling, reusable up to five recycle runs, easy separation, short reaction time, no need of time consuming column purification, high yielding, and so on. The synthesized catalyst and biscoumarin derivatives were well characterized by spectral analysis. The molecular modeling studies showed that the designed molecular scaffolds (3a‐j) showed outstanding interaction with methylenetetrahydrofolate reductase (MTHFR) and cytochrome P450 3A4 (CYP3A4) proteins. It was noticed that 3f (−17.55 kJ/mol) and 3d (−26.23 kJ/mol) showed the highest docking score against CYP3A4 and MTHFR proteins, respectively.

中文翻译:

单击化学启发设计,合成和分子对接研究双香豆素衍生物,使用碳基酸催化剂

已经描述了使用碳磺酸(一种固体载体催化剂)绿色环保地合成双香豆素衍生物。该反应涉及4-羟基香豆素和醛的一锅两组分反应,其中使用碳磺酸进行Knoevenegal-Michael缩合反应。一系列芳香族(带有电子吸收和释放基团)和杂芳香族醛已被转化为双香豆素,具有优异的分离收率。该反应符合绿色原理,即廉价的催化剂,易于制备,无毒,易于处理,最多可重复使用五个循环,易于分离,反应时间短,无需费时的柱纯化,高收率和以此类推。通过光谱分析对合成的催化剂和双香豆素衍生物进行了很好的表征。(3a-j)显示出与亚甲基四氢叶酸还原酶(MTHFR)和细胞色素P450 3A4(CYP3A4)蛋白的出色相互作用。注意到3f(−17.55 kJ / mol)和3d(−26.23 kJ / mol)分别显示了对CYP3A4和MTHFR蛋白的最高对接分数。
更新日期:2020-09-08
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