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Novel 4(3H)-quinazolinones containing biologically active thiazole, pyridinone and chromene of expected antitumor and antifungal activities
Khairy Abdel Hameed Mohsen El-Bayouki (1)
, Wahid Mohamed Basyouni (2) , Yahia Abdel Fatah Mohamed (3) , Mohsen Mohamed Aly (4) , Samir Youssef Abbas (5,*) (1) Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, 12311, Egypt
(2) Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, 12311, Egypt
(3) Department of Chemistry, Faculty of Science, Al-Azhar University, Cairo, 11884, Egypt
(4) Department of Chemistry, Faculty of Science, Al-Azhar University, Cairo, 11884, Egypt
(5) Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, 12311, Egypt
(*) Corresponding Author
Received: 16 Jun 2010 | Accepted: 03 Feb 2011 | Published: 31 Dec 2011 | Issue Date: December 2011
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.
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DOI: 10.5155/eurjchem.2.4.455-462.171
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