I 2 /TBHP mediated domino synthesis of 2-(2,4-dioxo-1,4-dihydroquinazolin-3(2 H )-yl)- N -aryl/alkyl benzamides and evaluation of their anticancer and docking studies.

Autor: Soda AK; Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology Hyderabad-500007 India sridharm@iict.res.in.; Academy of Scientific and Innovative Research (AcSIR) Ghaziabad-201002 India., C S PK; Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology Hyderabad-500007 India sridharm@iict.res.in., Chilaka SK; Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology Hyderabad-500007 India sridharm@iict.res.in.; Academy of Scientific and Innovative Research (AcSIR) Ghaziabad-201002 India., E VK; Academy of Scientific and Innovative Research (AcSIR) Ghaziabad-201002 India.; Applied Biology Division, CSIR-Indian Institute of Chemical Technology Hyderabad-500007 India., Misra S; Academy of Scientific and Innovative Research (AcSIR) Ghaziabad-201002 India.; Applied Biology Division, CSIR-Indian Institute of Chemical Technology Hyderabad-500007 India., Madabhushi S; Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology Hyderabad-500007 India sridharm@iict.res.in.; Academy of Scientific and Innovative Research (AcSIR) Ghaziabad-201002 India.
Jazyk: angličtina
Zdroj: RSC advances [RSC Adv] 2022 Jun 06; Vol. 12 (26), pp. 16589-16598. Date of Electronic Publication: 2022 Jun 06 (Print Publication: 2022).
DOI: 10.1039/d2ra02216h
Abstrakt: A novel I 2 /TBHP mediated domino synthesis of 2-(2,4-dioxo-1,4-dihydroquinazolin-3(2 H )-yl)- N -phenyl benzamides by reaction of isatins with o -amino N -aryl/alkyl benzamides was described. This was the first application of o -amino N -aryl/alkyl benzamides participating in oxidative rearrangement with isatins for synthesis of desired products. The synthesized compounds contained amide and quinazoline units and their combination resulted in molecular hybridization of two important pharmacophores. In this study, the synthesized compounds 3a-r were screened for cytotoxicity against four cancer cell lines A549, DU145, B16-F10, and HepG2 and also non-cancerous cell line CHO-K1. The compounds 3c, 3l and 3o gave promising results. The in silico molecular docking studies (PDB ID 1N37) also validated the anticancer activity of these compounds showing good binding affinity with target DNA and by acting as DNA intercalators.
Competing Interests: The authors declare that they have no conflict of interest.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE
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