Novel 4(3H)-quinazolinones containing biologically active thiazole, pyridinone and chromene of expected antitumor and antifungal activities
Open Access
- 31 December 2011
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 2 (4), 455-462
- https://doi.org/10.5155/eurjchem.2.4.455-462.171
Abstract
Novel 4(3H)-quinazolinone derivatives with biologically active moieties were synthesized. Reactions of 2-cyano-N-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl) acetamide with carbon disulfide, isothiocyanates followed by cycloalkylation afforded acrylamide, 1,3-dithiazole, 1,3-dithiane, thiazole and pyrazole derivatives. The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with some acetylacetone or arylidenes. Cyclocondensation reaction of cyanoacetamide with o-hydroxy aldehydes furnished chromene derivatives. Screening for some selected compounds was carried for their potential antitumor and antifungal activities. 2-Cyano-N-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2-(4-methyl-3-phenyl-thiazol-2(3H)ylidene)-acetamide with 3-side chain incorporated with substituted thiazole moiety was found to be of high to moderate activity towards cells. Also, the latter product showed high activity against Aspergillus ochraceus Wilhelm with inhibition zone (18 mm) compared with (20 mm) Nystatin inhibition zone.Keywords
This publication has 19 references indexed in Scilit:
- Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agentsEuropean Journal of Medicinal Chemistry, 2009
- CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-onesEuropean Journal of Medicinal Chemistry, 2008
- Synthesis and biological properties of 4-(3H)-quinazolone derivativesEuropean Journal of Medicinal Chemistry, 2007
- Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agentsEuropean Journal of Medicinal Chemistry, 2006
- Synthesis and Anti-inflammatory Evaluation of Some New Quinazoline DerivativesInternational Journal of Pharmacology, 2005
- Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chainsBioorganic & Medicinal Chemistry Letters, 2005
- Synthesis of Certain New 6-Iodoquinazolines as Potential Antitubercular AgentsJournal of Applied Sciences, 2004
- Some new 2,3,6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitorsBioorganic & Medicinal Chemistry, 2003
- A survey of reported synthesis of methaqualone and some positional and structural isomersForensic Science International, 2001
- The herbicidal activity of 2‐alkyl‐2‐cyanoacetanilidesPesticide Science, 1980