Click chemistry-inspired design,synthesis, and molecular docking studies of biscoumarin derivatives using carbon-based acid catalyst |
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| Authors: | Dinesh K. Agarwal Ayushi Sethiya Pankaj Teli Anu Manhas Jay Soni Nusrat Sahiba Prakash C. Jha Shikha Agarwal Pradeep K. Goyal |
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| Affiliation: | 1. Department of Pharmacy, B. N. University, Udaipur, Rajasthan, India;2. Synthetic Organic Chemistry Laboratory, Department of Chemistry, Mohan Lal Sukhadia University, Udaipur, Rajasthan, India;3. School of Chemical Sciences, Central University of Gujarat, Gandhinagar, Gujarat, India;4. School of Applied Material Sciences, Central University of Gujarat, Gandhinagar, Gujarat, India |
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| Abstract: | ![]()
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. |
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