European Journal of Chemistry

Novel 4(3H)-quinazolinones containing biologically active thiazole, pyridinone and chromene of expected antitumor and antifungal activities

Article Sidebar

PDF
Published: Dec 31, 2011
DOI: https://doi.org/10.5155/eurjchem.2.4.455-462.171
Keywords:
4(3H)-Quinazolinone, Thiazole, Pyridinone, Chromene, Antitumor, Antifungal activity
Section
Research Article
Issue
Vol. 2 No. 4 (2011): December 2011
Dates
Received 2010-06-16
Accepted 2011-02-03
Published 2011-12-31


Main Article Content

Khairy Abdel Hameed Mohsen El-Bayouki
Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, 12311, Egypt
Wahid Mohamed Basyouni
Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, 12311, Egypt
Yahia Abdel Fatah Mohamed
Department of Chemistry, Faculty of Science, Al-Azhar University, Cairo, 11884, Egypt
Mohsen Mohamed Aly
Department of Chemistry, Faculty of Science, Al-Azhar University, Cairo, 11884, Egypt
Samir Youssef Abbas
Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, 12311, Egypt

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.

2_4_455_462_800


icon graph This Abstract was viewed 3105 times | icon graph Article PDF downloaded 1117 times

How to Cite
(1)
El-Bayouki, K. A. H. M.; Basyouni, W. M.; Mohamed, Y. A. F.; Aly, M. M.; Abbas, S. Y. Novel 4(3H)-Quinazolinones Containing Biologically Active Thiazole, Pyridinone and Chromene of Expected Antitumor and Antifungal Activities. Eur. J. Chem. 2011, 2, 455-462.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Tiwari, A. K.; Singh, V. K.; Bajpai, A.; Shukla, G.; Singh, S.; Mishra, A. K. Eur. J. Med. Chem. 2007, 42, 1234-1238.
http://dx.doi.org/10.1016/j.ejmech.2007.01.002
PMid:17321640

[2]. Grover, G.; Kini, S. G. Eur. J. Med. Chem. 2006, 41, 256-262.
http://dx.doi.org/10.1016/j.ejmech.2005.09.002
PMid:16260068

[3]. Cao, S. L.; Feng, Y.-P.; Jiang, Y. Y. Biorg. Med. Chem. Lett. 2005, 15, 1915- 1917
http://dx.doi.org/10.1016/j.bmcl.2005.01.083

[4]. Giri, R. S.; Thaker. H. M.; Giordano, T.; Williams, J.; Rogers, D.; Sudersanam, V.; Vasu, K. K. Eur. J. Med. Chem. 2009, 44, 2184-2189.
http://dx.doi.org/10.1016/j.ejmech.2008.10.031
PMid:19064304

[5]. El-Helby, A. G. A.; Abdel Wahab, M. H. Acta Pharm. 2003, 53, 127-138.
PMid:14764247

[6]. Kadi, A. A.; El-Azab, A. S.; Alafeefy, A. M.; Abdel-Hamide, S. G. Al-Azhar J. Pharm. Sci. 2006, 34, 147-158.

[7]. Jatav, V.; Mishra, P.; Kashaw, S. Eur. J. Med. Chem. 2008, 43, 1945-1951.
http://dx.doi.org/10.1016/j.ejmech.2007.12.003
PMid:18222569

[8]. Van Zyl, E. F. A. Forensic Sci. Int. 2001, 122, 142-149.
http://dx.doi.org/10.1016/S0379-0738(01)00484-4

[9]. Kumar, A.; Sharma, S.; Bajaj, A. K.; Sharma, S.; Panwar, H.; Singh, N.; Srivastava, V. K. Bioorg. Med. Chem. 2003, 11, 5293- 5299.
http://dx.doi.org/10.1016/S0968-0896(03)00501-7

[10]. Mohamed, M. S.; Ibrahim, M. K.; Alafeefy, A. M.; Abdel-Hamide, S. G. J. Appl. Sci. 2004, 4, 302-307.
http://dx.doi.org/10.3923/jas.2004.302.307

[11]. Mohamed, M. S.; Ibrahim, M. K.; Alafeefy, A. M.; Abdel-Hamide, S. G. Int. J. Pharmacol. 2005, 1, 261-265.
http://dx.doi.org/10.3923/ijp.2005.261.266

[12]. Geissler, A. E.; Huppatz J. L.; Phillips, J. N. Pesticide Sci. 1980, 11(4), 432-438.
http://dx.doi.org/10.1002/ps.2780110410

[13]. Wayne, J. W. O.; Seidel M. C.; Harlow, W. L. US Patent, (1977) 4, 038, 065, Chem. Abstr. 1977, 87: 152034y.

[14]. Roifman, C. M.; Aviv G.; Alexander, L. PCT Int . Appl. WO Patent, (2000) 0055, 128, Chem. Abstr. (2000)133: 237695h.

[15]. Fahmy, H. T.; Rostom, S. A.; Bekhit, A. A. Archiv der Pharmazie 2002, 335(5), 213-222.
http://dx.doi.org/10.1002/1521-4184(200205)335:5<213::AID-ARDP213>3.0.CO;2-H

[16]. Ismail, M. M. F.; Ammar, Y. A.; El-Zahaby, H. S. A.; Eisa S. I.; Barakat, S. E. Archiv der Pharmazie 2007, 340, 476-482.
http://dx.doi.org/10.1002/ardp.200600197
PMid:17647214

[17]. Sathisha, M. P.; Shetti, U. N.; Revankar, V. K. and Pai, K. S. R. Eur. J. Med. Chem. 2008, 43(11), 2338-2346.
http://dx.doi.org/10.1016/j.ejmech.2007.10.003
PMid:18023933

[18]. NazAgh-Atabay, M.; Dulger, B.; Gucin, F. Microbiological Methods, sixth Ed. Butterworths Co. Ltd., London, (1989).

[19]. Performance Standards for Antimicrobial Disk Suspectibility Tests, Approved Standard NCCLS Publication M2-A5, Villanova, PA, USA, 1993, pp. 1-32.

[20]. Mohamed, Y. A.; Aziza, M. A. E.; Salama, F. M.; Alafify, A. M. J. Serb. Chem. Soc. 1992, 57(10), 629-633.

[21]. Dolle, V.; Fan, E.; Ngugen, C. H.; Aubertin, A. M.; Bisagui, E. A. J. Med. Chem. 1995, 38, 4679-4686.
http://dx.doi.org/10.1021/jm00023a007
PMid:7473595

[22]. Wai, J. S.; Williams, T. M.; Bamberey, D. L.; Anderson, P. S. J. Med. Chem. 1993, 36, 249-255.
http://dx.doi.org/10.1021/jm00054a009
PMid:7678654

[23]. Veale, C. A.; Bernstein P. R.; Brynat, C.; Cessorelli, C.; Woolson, S. J. Med. Chem. 1995, 38, 98-108.
http://dx.doi.org/10.1021/jm00001a015
PMid:7837246

[24]. Zhang, Y. Y.; Meng, X. M.; Wang, X. L.; Xu, L. X. Dyes and Pigment 2003, 56, 189-194.
http://dx.doi.org/10.1016/S0143-7208(02)00144-4

[25]. Christie R. M.; Chih-Hung L. Dyes and Pigments 1999, 42, 85-93.
http://dx.doi.org/10.1016/S0143-7208(99)00012-1

[26]. Sasaki, K. Jpn. Kokai Tokkyo Koho (1994) 23 05, 190, 902; Chem. Abst. 1994, 120:310929a

[27]. Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Detsi, A.; Koufaki, M.; Kontogiorgis, C.; Hadjipavlou-Litina D. J. Eur. J. Med. Chem. 2009, 44, 3020-3026.
http://dx.doi.org/10.1016/j.ejmech.2008.12.027
PMid:19232783

Supporting Agencies

Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).