Efficient One-pot Synthesis, Antimicrobial and Docking Studies of Some Newer Tetrahydro-4H-benzo [1,3-e]oxazines and Related β-Acylamino Ketone Derivatives
Corresponding Author
Khairy A. M. El-Bayouki
Organometallic and Organometalloid Chemistry Department, National Research Centre, Dokki, Cairo, Egypt
E-mail: [email protected]Search for more papers by this authorWahid M. Basyouni
Organometallic and Organometalloid Chemistry Department, National Research Centre, Dokki, Cairo, Egypt
Search for more papers by this authorTamer K. Khatab
Organometallic and Organometalloid Chemistry Department, National Research Centre, Dokki, Cairo, Egypt
Search for more papers by this authorEzzat M. Kandel
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt
Search for more papers by this authorDoria S. Badawy
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt
Search for more papers by this authorEbrahim Abdel-Galil
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt
Search for more papers by this authorAhmed A. El-Henawy
Chemistry Department, Faculty of Science, Al-Azhar University, Cairo, Egypt
Search for more papers by this authorCorresponding Author
Khairy A. M. El-Bayouki
Organometallic and Organometalloid Chemistry Department, National Research Centre, Dokki, Cairo, Egypt
E-mail: [email protected]Search for more papers by this authorWahid M. Basyouni
Organometallic and Organometalloid Chemistry Department, National Research Centre, Dokki, Cairo, Egypt
Search for more papers by this authorTamer K. Khatab
Organometallic and Organometalloid Chemistry Department, National Research Centre, Dokki, Cairo, Egypt
Search for more papers by this authorEzzat M. Kandel
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt
Search for more papers by this authorDoria S. Badawy
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt
Search for more papers by this authorEbrahim Abdel-Galil
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt
Search for more papers by this authorAhmed A. El-Henawy
Chemistry Department, Faculty of Science, Al-Azhar University, Cairo, Egypt
Search for more papers by this authorAbstract
A concise one-step procedure was developed for the synthesis of some newer tetrahydro-4H-benzo[1,3-e]oxazines and β-acylamino ketone derivatives via condensation of cyclohexanone derivative with different aromatic aldehydes and nitriles in the presence of tetrachlorosilane/zinc chloride (TCS/ZnCl2) reagent mixture under ambient conditions. Docking studies for the synthesized benzo-oxazine derivatives were designed and a model of highly active derivatives was mapped for the antimicrobial screening.
References and Notes
- 1Basyouni, W. M.; El-Bayouki, K. A. M.; Tohamy, W. M.; Abbas, S. Y. Synthetic Comm 2015, 45, 1073.
- 2Schreiber, S. L. Chem Eng News 2003, 81, 51.
- 3Lokey, R. S. Curr Opin Chem Biol 2003, 7, 91.
- 4Lee, D.; Sello, J. K.; Schreiber, S. L. Org Lett 2000, 2, 709.
- 5Portlock, D. E.; Ostaszewski, R.; Naskar, D.; West, L. Tetrahedron Lett 2003, 44, 603.
- 6Nüske, H.; Bräse, S.; Kozhushkov, S. I.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem Eur J 2002, 8, 2350.
10.1002/1521-3765(20020517)8:10<2350::AID-CHEM2350>3.0.CO;2-E CAS PubMed Web of Science® Google Scholar
- 7De Meijere, A.; Nüske, H.; Es-Sayed, M.; Labahn, T.; Schroen, M.; Bras̈e, S. Angew Chem Int Ed 1999, 38, 3669.
10.1002/(SICI)1521-3773(19991216)38:24<3669::AID-ANIE3669>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- 8El-Bayouki, K. A. M.; Basyouni, W. M.; El-Sayed, A. S.; Tohamy, W. M.; El-Henawy, A. A. Croat Chem Acta 2012, 85, 255.
- 9Basyouni, W. M.; El-Bayouki, K. A. M.; El-Sayed, A. S.; Tohamy, W. M.; Farag, M. M. S.; Abd El-Baseer, M. A. Drug Res 2015, 65, 473.
- 10Marcaccini, S.; Pepino, R.; Polo, C.; Pozo, M. C. Synthesis 2001, 85.
- 11Khatab, T. K.; El-Bayouki, K. A. M.; Basyouni, W. M.; El-Basyoni, F. A.; Ali, M. M.; Abbas, S. Y.; Mostafa, E. A. Res J Pharm Biol Chem Sci 2015, 6, 281.
- 12(a) Barriga, S.; Fuertes, P.; Marcos, C. F.; Rakitin, O. A. Torroba, TJ Org Chem 2002, 67, 6439; (b) Barriga, S.; Marcos, C. F.; Riant, O.; Torroba, T. Tetrahedron 2002, 58, 9785.
- 13Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley and Sons: New York, NY, 1989, pp 423.
- 14Kobayashi, M.; Kitazawa, M.; Sotio, T.; Yamamoto, R.; Harada, H. Yakugaku Zasshi 1984, 104, 659; Chem Abstr 1985, 102: 6344 m.
- 15(a) Raynaud, G.; Sergant, M.; Douzon, C.; Fauran, C.; U.S. 3,821,215,1974; Chem Abstr 1975, 82:49951r; (b) Vrouenraets, S. M.; Wit, F. W.; van Tongeren, J.; Lange, J. M. Expert Opin Pharmacother 2007, 8, 851.
- 16(a) Abbas, S. Y.; Farag, A. A.; Ammar, Y. A.; Atrees, A. A.; Mohamed, A. F.; El-Henawy, A. A. Monatsh Chem 2013, 144, 1725; (b) Helal, M. H.; Abbas, S. Y.; Salem, M. A.; Farag, A. A.; Ammar, Y. A. Med Chem Res 2013, 22, 5598.
- 17(a) Herges, R.; Strack, F. J Am Chm Soc 1996, 118, 12752; (b) Salama, T. A.; El-Ahl, A. S.; Khalil, A. M.; Girges, M. M.; Lackner, B.; Stiendl, C.; Elmorsy, S. S. Monatsh Chem 2003, 134, 1241; (c) Esikov, K. A.; Morozova, S. E.; Malin, A. A.; Ostrovskii, V. A. Russ J Org Chem 2002, 38, 1370; (d) Morozova, S. E.; Esikov, K. A.; Dmitrieva, T. N.; Malin, A. A.; Ostrovskii, V. A. Russ J Org Chem 2004, 40, 443.
- 18Ha, D. S.; Kim, H. A. J. Korean Chem Soc 1997, 41, 535.
- 19Ha, D. S.; Yoon, M. J. J Korean Chem Soc 1997, 41, 541.
- 20Salama, T. A.; Elmorsy, S. S.; Khalil, A. M. Tetrahedron Lett 2007, 48, 4395.
- 21(a) Salama, T. A.; Elmorsy, S. S.; Khalil, A. M.; Ismail, M. A. Tetrahedron Lett 2007, 48, 6199; (b) Khatab, T. K.; Elmorsy, S. S.; Badawy, D. S. Phosphorus, Sulfur, Silicon 2005, 180, 109.
- 22Badawy, D. S.; Abdel-Galil, E.; Kandeel, E. M.; Basyouni, W. M.; El-Bayouki, K. A. M.; Khatab, T. K. Phosphorus, Sulfur, Silicon 2009, 184, 220.
- 23Badawy, D. S.; Abdel-Galil, E.; Kandeel, E. M.; Basyouni, W. M.; Khatab, T. K. Phosphorus, Sulfur, Silicon 2009, 184, 2799.
- 24Khatab, T. K.; El-Bayouki, K. A. M.; Basyouni, W. M. Tetrahedron Lett 2011, 52, 1448.
- 25(a) Hayashi, M.; Inubushi, A.; Mukaiyama, T. Bull Chem Soc Jpn 1988, 61, 4037; (b) Elmorsy, S. S.; Badawy, D. S.; Khatab, T. K. Phosphorus, Sulfur, Silicon 2006, 181, 2005.
- 26Cook, D. Can J Chem 1963, 41, 522.
- 27Kabalka, G. W.; Tejedor, D.; Li, M.-S.; Malladi, R. R.; Troman, S. J Org Chem 1998, 63, 6438.
- 28Aizpurua, J. M.; Palomo, C. Anales de Quimica 1987, 83, 121.
- 29Terenin, V. I.; Kontarev, P. G.; Maloshitskaya, O. A.; Kabanova, E. V. Chem Heterocyl Comp (N-Y) 1997, 33, 318.
- 30Richard, R. S.; Synthesis, Reviews, 1972, 333.
- 31Deans, S. G.; Ritchie, G. A.; International, J. Food Microbial 1987, 5, 165.
- 32Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv Drug Delivery Rev 1997, 23, 3.
- 33Clark, D. E.; Pickett, S. D. Drug Discov Today 2000, 5, 49.
- 34 MOE, 2009.10 of Chemical Computing Group. Inc.
- 35Wildman, S. A.; Crippen, G. M. J Chem Inf Comput Sci 1999, 39, 868.
- 36Profeta, S.; Allinger, N. L. J Am Chem Soc 1985, 107, 1907.
- 37Halgren, T. A. J Comput Chem 1996, 17, 490.
- 38Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J Am Chem Soc 1985, 107, 3902.
- 39Muir, A. D.; Cole, A. L. J.; Walker, J. R. L. Planta Med 1982, 44, 129.
