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One-pot Synthesis, Anticancer Evaluation, and Molecular Modelling Studies of New Quinazolin-4(1H)-one Derivatives

A green one-pot synthesis of 3,3′-(1,4-phenylene)bis[2-(furan/thiophen/pyrrol-2-yl)-2,3-dihydro­quinazolin-4(1 H )-one] derivatives in 85–90% yield have been developed by using 1 H -1,3-benzoxazine-2,4-dione, furane-, thiophene-, or 1 H -pyrrole-2-carbaldehyde, and benzene-1,4-diamine as starting ma...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2023-09, Vol.59 (9), p.1583-1590
Main Authors: Srinivas, A., Shree, A. Jaya, Goud, S. S. Kumar
Format: Article
Language:English
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Summary:A green one-pot synthesis of 3,3′-(1,4-phenylene)bis[2-(furan/thiophen/pyrrol-2-yl)-2,3-dihydro­quinazolin-4(1 H )-one] derivatives in 85–90% yield have been developed by using 1 H -1,3-benzoxazine-2,4-dione, furane-, thiophene-, or 1 H -pyrrole-2-carbaldehyde, and benzene-1,4-diamine as starting materials in the presence of L-proline as catalyst in ethanol at 65–70°C for 90–120 min. The anticancer potential of the synthesized compounds against SKOV3 and DU145 cells has been evaluated, and 1-methyl-5-nitro-1 H -pyrrol-2-yl derivative 4h exhibited the prominent activity against SKOV3 and DU145 cells with an IC 50 values of 8.5 and 7.9 µM, respectively. The in silico study of the most active compound (–10.8 kcal/mol) showed good binding energies toward human mitogen-activated protein kinase.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023090166