Utility of 2-Methyl-quinazolin-4(3H)-one in the Synthesis of Heterocyclic Compounds with Anticancer Activity
Open Access
- 1 January 2014
- journal article
- Published by Scientific Research Publishing, Inc. in Open Journal of Medicinal Chemistry
- Vol. 04 (01), 12-37
- https://doi.org/10.4236/ojmc.2014.41002
Abstract
Quinolino[2,1-b]quinazolines 3 and 4, pyrrolo[2,1-b]quinazoline 5 and various substituted 2-(4-chlorostyryl)quinazoline derivatives including: 4-amino derivative 8, 4-hydrazino derivative 9, thiourea derivative 10, thiosemicarbazide derivative 19, 4-benzylidene hydrazinyl derivative 21, 4-amino thiazolidene derivatives 11, 12, 13, 22, imidazoquinazolines 15, 16, quinazolinium chloride 14, triazino[4,3-c]quinazolines 17, 18, tetrazino[1,6-c]quinazoline 20, 4-amino azetidinyl derivative 23, triazolo[4,3-c]quinazoline 24, 4-amino substituted quinazolines 25, 26, 27, 29 and quinazolino quinazoline 28 were synthesized through different chemical reactions. The obtained compounds were evaluated for their in vitro antitumor activity against HEPG2 and MCF-7 cell lines compared to the reference drug (doxorubicin). Compounds 18, 19, 20, 23 and 24 were found to be the most active against both cell lines exhibiting IC50 values ranging from 10.82 - 29.46 μM/L and 7.09 - 31.85 μM/L against Hep-G2 and MCF-7 cell lines, respectively, in addition to docking study of these five compounds against thymidylate synthase and dihydrofolate reductase enzymes active sites.Keywords
This publication has 35 references indexed in Scilit:
- Molecular modeling study and synthesis of quinazolinone-arylpiperazine derivatives as α1-adrenoreceptor antagonistsEuropean Journal of Medicinal Chemistry, 2011
- Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: Molecular docking studyEuropean Journal of Medicinal Chemistry, 2010
- Identification and optimization of novel 2-(4-oxo-2-aryl-quinazolin-3(4H)-yl)acetamide vasopressin V3 (V1b) receptor antagonistsBioorganic & Medicinal Chemistry Letters, 2010
- Hybrid diarylbenzopyrimidine non-nucleoside reverse transcriptase inhibitors as promising new leads for improved anti-HIV-1 chemotherapyBioorganic & Medicinal Chemistry, 2010
- Development of thioquinazolinones, allosteric Chk1 kinase inhibitorsBioorganic & Medicinal Chemistry Letters, 2009
- Discovery and structure–activity relationships of 4-aminoquinazoline derivatives, a novel class of opioid receptor like-1 (ORL1) antagonistsBioorganic & Medicinal Chemistry, 2009
- Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-dionesInvestigational New Drugs, 2008
- Synthesis and anticonvulsant activity of some novel 3-aryl amino/amino-4-aryl-5-imino-Δ2-1,2,4-thiadiazolineEuropean Journal of Medicinal Chemistry, 2008
- Synthesis and antileukemic activity of new 3-(5-methylisoxazol-3-yl) and 3-(pyrimidin-2-yl)-2-styrylquinazolin-4(3H)-onesIl Farmaco, 2004
- Thermal cyclization of 4‐azido‐3‐nitropyridines to furoxanesJournal of Heterocyclic Chemistry, 2000