Click chemistry-inspired design, synthesis, and molecular docking studies of biscoumarin derivatives using carbon-based acidcatalyst

被引：11

作者：

Agarwal, Dinesh K. ^{[1
]}

Sethiya, Ayushi ^{[2
]}

Teli, Pankaj ^{[2
]}

Manhas, Anu ^{[3
]}

Soni, Jay ^{[2
]}

Sahiba, Nusrat ^{[2
]}

Jha, Prakash C. ^{[4
]}

Agarwal, Shikha ^{[2
]}

Goyal, Pradeep K. ^{[1
]}

机构：

[1] BN Univ, Dept Pharm, Udaipur, Rajasthan, India

[2] Mohan Lal Sukhadia Univ, Dept Chem, Synthet Organ Chem Lab, Udaipur 313001, Rajasthan, India

[3] Cent Univ Gujarat, Sch Chem Sci, Gandhinagar, Gujarat, India

[4] Cent Univ Gujarat, Sch Appl Mat Sci, Gandhinagar, Gujarat, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2020年 / 57卷 / 09期

关键词：

ONE-POT SYNTHESIS; CATALYST-FREE SYNTHESIS; HIGHLY EFFICIENT; DIHYDROPYRAN DERIVATIVES; GREEN SYNTHESIS; ACID CATALYST; BIS-COUMARIN; NANOPARTICLES; NANOCATALYST; ANTICANCER;

D O I：

10.1002/jhet.4045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 that3f(-17.55 kJ/mol) and3d(-26.23 kJ/mol) showed the highest docking score against CYP3A4 and MTHFR proteins, respectively.

引用

页码：3294 / 3309

页数：16

共 78 条

[1]

*ACC SOFTW INC, DISC STUD VERS 4 0

[2] The magnetic nanostructured natural hydroxyapatite (HAP/Fe3O4 NPs): an efficient, green and recyclable nanocatalyst for the synthesis of biscoumarin derivatives under solvent-free conditions [J].