Synthesis and assessment of the cytotoxic effects of some of Novel Biginelli 3,4-dihydropyrmidine-2-(1H) one derivatives Containing 2-mercapto-3-phenyl-4(3H)-quinazolinone.-Reference-Cited by-同舟云学术

Synthesis and assessment of the cytotoxic effects of some of Novel Biginelli 3,4-dihydropyrmidine-2-(1H) one derivatives Containing 2-mercapto-3-phenyl-4(3H)-quinazolinone.

Published:2022-08-16 Issue: Volume: Page:
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Author:

Nouri Mojtaba¹,Pirmohammadi Nasim¹,dilmaghani karim akbari¹^ORCID,Pazhang Yaghub¹

Affiliation:

1. Urmia University

Abstract

Abstract In the present study, a new series of 3,4- dihydropyrmidine2-(1 H) one derivatives(4a-f) which linked to 2-mercapto-3-phenyl-4(3H)-quinazolinone were synthesized by using the nucleophilic substitution reaction of 2-mercapto-3-phenyl-4(3H)-quinazolinone (1) and an appropriate 6-bromomethyl-3,4- dihydropyrmidine2-(1 H) one (3a-f) in the presence of KOH as base and in CH3CN as solvent. The chemical structures of the synthesized compounds were confirmed by means of IR, 1H-NMR, 13C-NMR, Mass spectroscopy, and Elemental analysis. The cytotoxicity of the newly synthesized compounds was evaluated in vitro against the human breast cancer (MCF-7) cell line and human colon cancer cell line (HT-29) based on the results of the MTT assay. Our results indicated that the compound 4b exerted the most cytotoxic effect in the two cell lines and the IC50 values were (4.25±0.16 μM) for MCF-7 cell lines and (12.11±0.76 μM) for HT-29 cell lines. Also, compound 4b induced apoptosis more than other compounds in the two cell lines. Therefore, compound 4b may be a potential anticancer agent.

Publisher

Research Square Platform LLC

Reference35 articles.

1. Ahmedin Jemal, and Freddie Bray. "Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries;Sung H;Cancer J Clin,2021

2. Yeldag G (2018) Alistair Rice, and Armando del Río Hernández. "Chemoresistance and the self-maintaining tumor microenvironment." Cancers 10, no. 12 : 471

3. Akberali. "One pot synthesis of thiazolodihydropyrimidinones and evaluation of their anticancer activity;Holla B;Eur J Med Chem,2004

4. Liu Y, Liu J, Zhang R, Guo Y, Wang H, Meng Q, Sun Y, Liu Z (2019) "Synthesis, characterization, and anticancer activities evaluation of compounds derived from 3, 4-dihydropyrimidin-2 (1H)-one." Molecules 24, no. 5 : 891

5. Bhat MA, Al-Dhfyan A, Mohamed A, Al-Omar (2016) "Targeting cancer stem cells with novel 4-(4-Substituted phenyl)-5-(3, 4, 5-trimethoxy/3, 4-dimethoxy)-benzoyl-3, 4-dihydropyrimidine-2 (1H)-one/thiones." Molecules 21, no. 12 : 1746