Synthesis of New Benzoxazinone, Quinazolinone, and Pyrazoloquinazolinone Derivatives and Evaluation of Their Cytotoxic Activity Against Human Breast Cancer Cells
Loading...
Date
2018-05
Authors
Journal Title
Journal ISSN
Volume Title
Type
Article
Publisher
WILEY, 111 RIVER ST
Series Info
JOURNAL OF HETEROCYCLIC CHEMISTRY;Volume: 55 Issue: 5 Pages: 1223-1231
Doi
Scientific Journal Rankings
Abstract
Synthesis of 2-[3-(3,4-dichlorophenyl)-3-oxoprop-1-enyl]-4H-benzo[3,1]oxazin-4-one 2 as a precursor to synthesize quinazolinones 5, 7 pyrazolylquinazolinones, 4, 12, 13, 14, 16 benzothiazine thione 10, benzene derivative 3 pyrroloquinazolinone 6, benzoimidazoquinazolinone 8, and pyrazolotriazepinoquinazolinone 15. The structures of the newly synthesized compounds were established by their elemental analyses and spectral data. Most of the synthesized compounds exhibited high antitumor and cytotoxic activity against human breast cancer cells.
Description
Accession Number: WOS:000433582600018
Keywords
KINASE, DOCKING, AGENTS, POTENT, INHIBITORS, MINERALOCORTICOID RECEPTOR ANTAGONISTS
Citation
El‐hashash, M. A.; El‐Naggar, A. M.; El‐Bordany, E. A.; Marzouk, M. I.; Nawar, T. M. S. Synth Commun 2016, 46, 2009. Crossref CAS Web of Science®Google Scholar 2Magdy, M.; Hemdan, M. M.; El‐Bordany, E. Chem Pap 2016, 70, 1117. Web of Science®Google Scholar 3Elziaty, A. K.; Mostafa, O. E. A.; El‐Bordany, E. A.; Nabil, M.; Madkour, H. M. F. Int J Sci Eng Res 2014, 5, 2229. Google Scholar 4El‐hashash, M. A.; El‐Naggar, A. M.; El‐Bordany, E. A.; Marzouk, M. I.; Nawar, T. M. S. Synth Commun 2016, 46, 1230. Crossref CAS Web of Science®Google Scholar 5Wu, W. H.; Chen, T. Y.; Lu, R. W.; Chen, S. T.; Chang, C. C. Phytochemistry 2012, 83, 110. Crossref CAS PubMed Web of Science®Google Scholar 6Mahmoud, R. M.; El‐Bordany, E. A.; Azab, M. E.; Soliman, E. A. J Phosphorus Sulfur Silicon 2007, 181, 1275. Crossref CAS Web of Science®Google Scholar 7Mahmoud, R. M.; El‐Bordany, E. A.; Hassan, N. F.; Abu El‐Azm, F. S. M. J Chem Res 2007, 2007, 541. CrossrefGoogle Scholar 8Niemeyer, H. M. J Agric Food Chem 2009, 57, 1677. Crossref CAS PubMed Web of Science®Google Scholar 9Nguyen, K. T.; Li, F.; Poda, G.; Smil, D.; Vedadi, M.; Schapira, M. J Chem Inf Model 2013, 53, 681. Crossref CAS PubMed Web of Science®Google Scholar 10Borate, H. B.; Maujan, S. R.; Sawargave, S. P.; Chandavarkar, M. A.; Vaiude, S. R.; Joshi, V. A.; Wakharkar, R. D.; Iyer, R.; Kelkar, R. G.; Chavan, S. P.; Kunte, S. S. Bioorg Med Chem Lett 2010, 22, 722. Crossref Web of Science®Google Scholar 11Fringuelli, R.; Giacche, N.; Milanese, L.; Cenci, E.; Macchiarulo, A.; Vecchiarelli, A.; Costantino, G.; Schiaffella, F. Bioorg Med Chem 2009, 17, 3838. Crossref CAS PubMed Web of Science®Google Scholar 12Rajitha, C.; Dubey, P. K.; Sunku, V.; Piedrafita, F. J.; Veeramaneni, V. R.; Pal, M. Eur J Med Chem 2011, 46, 4887. Crossref CAS PubMed Web of Science®Google Scholar 13Hasui, T.; Ohra, T.; Ohyabu, N.; Asano, K.; Matsui, H.; Mizukami, A.; Habuka, N.; Sogabe, S.; Endo, S.; Siedem, C. S.; Tang, T. P.; Gauthier, C.; De Meese, L. A.; Boyd, S. A.; Fukumoto, S. Bioorg Med Chem 2013, 21, 5983. Crossref CAS PubMed Web of Science®Google Scholar 14Wang, A.; Prouty, C. P.; Pelton, P. D.; Yong, M.; Demarest, K. T.; Murray, W. V.; Kuo, G. H. Bioorg Med Chem Lett 2010, 20, 1432. Crossref CAS PubMed Web of Science®Google Scholar 15Matralis, A. N.; Katselou, M. G.; Nikitakis, A.; Kourounakis, A. P. J Med Chem 2011, 54, 5583. Crossref CAS PubMed Web of Science®Google Scholar 16Hasui, T.; Matsunaga, N.; Ora, T.; Ohyabu, N.; Nishigaki, N.; Imura, Y.; Igata, Y.; Matsui, H.; Motoyaji, T.; Tanaka, T.; Habuka, N.; Sogabe, S.; Ono, M.; Siedem, C. S.; Tang, T. P.; Gauthier, C.; De Meese, L. A.; Boyd, S. A.; Fukumoto, S. J Med Chem 2011, 54, 8616. Crossref CAS PubMed Web of Science®Google Scholar 17Geng, B.; Comita‐Prevoir, J.; Eyermann, C. J.; Reck, F.; Fisher, S. Bioorg Med Chem Lett 2011, 21, 5432. Crossref CAS PubMed Web of Science®Google Scholar 18Mahmud, T. H. K.; Rasool, K.; Yimingjiang, W.; Mohammad, A.; Manzoor, A.; Ingebrigt, S. Bioorg Med Chem 2010, 18, 4317. Crossref PubMed Web of Science®Google Scholar 19Jatav, V.; Mishra, P.; Kashaw, S.; Stables, J. P. Eur J Med Chem 2008, 43, 135. Crossref CAS PubMed Web of Science®Google Scholar 20Alagarsamy, V.; Meena, S.; Ramaseshu, K. V.; Solomon, V. R.; Kumar, T. D.; Thirumurugan, K. Chem Biol Drug Des 2007, 70, 254. Wiley Online Library CAS PubMed Web of Science®Google Scholar 21El‐serwy, W. S.; Mohamed, N. A.; Emad, M. M.; Kassem, E. M. M.; Mahmoud, K.; Mounier, M. M. Iran J Pharm Res 2016, 15, 179. CAS PubMed Web of Science®Google Scholar 22Fathalla, O. A.; Kassem, E. M.; Ibrahem, N. M.; Kamel, M. M. Acta Pol Pharm 2008, 65, 11. CAS PubMed Web of Science®Google Scholar 23Kumar, A.; Sharma, S.; Archana; Bajaj, K.; Sharma, S.; Panwar, H.; Singh, T.; Srivastava, V. K. Bioorg Med Chem 2003, 11, 5293. Crossref CAS PubMed Web of Science®Google Scholar 24Zheng, L. W.; Shao, J. H.; Zhao, B. X.; Miao, J. Y. Med Chem Lett 2011, 21, 3909. Crossref CAS PubMed Web of Science®Google Scholar 25Hansen, J. D.; Grina, J.; Newhouse, B.; Welch, M.; Topalov, G.; Littman, N.; Callejo, M.; Gloor, S.; Martinson, M.; Laird, E.; Brandhuber, B. J.; Vigers, G.; Morales, T.; Woessner, R.; Randolph, N.; Lyssikatos, J.; Olivero, A. Bioorg Med Chem Lett 2008, 18, 4692. Crossref CAS PubMed Web of Science®Google Scholar 26Newhouse, B. J.; Hansen, J. D.; Grina, J.; Welch, M.; Topalov, G.; Littman, N.; Callejo, M.; Martinson, M.; Galbraith, S.; Laird, E. R.; Brandhuberm, B. J.; Vigers, G.; Morales, T.; Woessner, R.; Randolph, N.; Lyssikatos, J.; Olivero, A. Bioorg Med Chem Lett 2011, 21, 3488. Crossref CAS PubMed Web of Science®Google Scholar 27Choi, W. K.; El‐Gamal, M. I.; Choi, H. S.; Baek, D.; Oh, C. H. Eur J Med Chem 2011, 46, 5754. Crossref CAS PubMed Web of Science®Google Scholar 28Madkour, H. M. F.; Soliman, E. A.; Salem, M. A. I.; El‐Bordany, E. A. A. Bull Acad Pol 1999, 47, 217. CAS Web of Science®Google Scholar 29Repetto, G.; Del Peso, A.; Zurita, L. J. Nat Protoc 2008, 3, 1125.