Pharmacological Profile of Oxazine and its Derivatives: A Mini Review

Document Type: Review

Authors

1 Department of Pharmacy, Himalayan Institute of Pharmacy and Research, Dehradun, (Uttarakhand), 248007, India

2 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Northern Border University, Rafha 91911, PO Box 840, Saudi Arabia

Abstract

Oxazine derivatives are significant class of heterocycle compounds, which has involved much synthetic attention due to their extensive variety of pharmacological activities. Oxazine is a heterocyclic compound can be formally derived from benzene, and its reduction products, by suitable substitution of carbon (and hydrogen) atoms by nitrogen and oxygen. In the last few years oxazine derivatives have proved to be valuable synthetic intermediates and also possess important biological activities like sedative, analgesic, antipyretic, anticonvulsant, antitubercular, antitumour, antimalarial and antimicrobial. In these days, progress of drug resistance is a most important difficulty and to overcome this situation, it is necessary to synthesize new classes of compounds. The aim of the article is to review the generalization of the collected data about the synthesis of oxazine derivatives and their activities. We expect that this effort will be a specific interest for researchers concerned with oxazine derivatives.

Keywords


      [1]       Raj K. Bansal, Heterocyclic Chemistry, Fourth edition; New Age International Publishers; 501-502.
      [2]       Alan R. Katritzky, the Principles of Heterocyclic Chemistry; Pharma Med Press Publishers; 80-81.
      [3]       R. Morrin Acheson, An Introduction to the Chemistry of Heterocyclic Compounds, Third edition; A Wiely -Inter Science Publication; 410-414.
      [4]       T. Zuhal, P. Emel, K. Adem, Molecules., 12, 345 (2007).
      [5]       N. Siddiqui, R. Ali, M. S. Alam, W. J. Ahsan, Chem. Pharm. Res., 2, 309 (2010).
      [6]       T. J. Sindhu, S. D. Arikkatt, G. Vincent, M. Chandran, A. R. Bhat, K. Krishna Kumar, Inter. J. Pharma. Sci. Res., 4, 134 (2013).
      [7]       P. M. Cox, N. N. Bumpus, Med. Chem. Lett., 5, 1156 (2014).
      [8]       Mohasseb, Int. J. New. Chem., 6, 215 (2019).
      [9]       Modak, U. Dutta, R. Kancherla, S. Maity, M. Bhadra, S. M. Mobin, D. Maiti, Org. Lett., 16, 2602 (2014).
     [10]     L. Moreno, N. Cabedo, A. Boulangé, J. Párraga, A. Galán, S. Leleu, M. J. Sanz, D. Cortes, X. Franck, Eur. J. Med. Chem., 69, 69 (2013).
     [11]     F. Slowinski, O. Ben Ayad, O. Ziyaret, C. Botuha, L. Le Falher, K. Aouane, S. Thorimbert, Org. Lett., 15, 3494 (2013).
     [12]     S. Hossan, H. M. Abu-Melha, M. A. Al-Omar, A. G. Amr, Molecules., 2012; 17, 13642 (2012).
     [13]     Liu, T. F. Molinski, Chem. Asian. J., 6, 2022 (2011).
     [14]     R. Bhat, P. D. Pawar, Indian. Drugs., 45, 962 (2008).
     [15]     K. P. Beena, T. Akelesh, Schol. Res. Library., 2013, 5(4): 257-260.
     [16]     S. D. Sayaji, B. P. Piste, Internet. J. chem. Tech. Res., 5, 2199 (2013).
     [17]     D. Sunil, S. Upadhya, M. Rama, Res. J. Pharma. Sci., 2, 15 (2013).
     [18]     N. M. Anil, Int. J. Chem., 3, 74 (2011).
     [19]     S. D. Sayaji, B. P. Pravina, J. C. P. R., 5 271 (2013).
     [20]     L. S. Ramesh, S. M. Mahesh, B. W. Jyoti, B. Wadekar, Internet. J. Pharm. Tec. Res., 4, 1653 (2012).
     [21]     N. Zanatta, D. M. Borchhardt, S. H. Alves, M. C. Squizani, T. M. Marchi, H. G. Bonacorso, M. P. Martins, Bio. Org. Med. Chem., 14, 3174 (2006).
     [22]     T. Besson, C. W. Rees, G. Cottenceau, A. Pons, Bioorg. Med. Chem. Lett.,6, (1996).
     [23]     S. Ozden, A. Ozturk, H. Goker, N. Altanlar, I. L. Farma, 55, 715 (2000).
     [24]     R. Fringuelli, D. Pietrella, F. Schiaffella, A. Guarraci, S. Perito, F. Bistoni, A. Vecchiarilli, Bioorg. Med. Chem.,10, 1681 (2002).
     [25]     S. Alper-Hayta, E. Aki-Sener, B. Tekiner-Gulbas, I. Yildiz, T. Yalcin, N. Alanlar, Eur. J. Med. Chem.,41, 1398 (2006).
     [26]     B. P. Mathew, A. Kumar, S. Sharma, P. K. Shukla, M. Nath, Eur. J. Med. Chem.,45, 1502 (2010).
     [27]     K. Waisser, J. Gregor, L. Kubicova, V. Klimesova, J. Kunes, M. Machacek, J. Kaustova, Eur. J. Med. Chem.,35, 733 (2000).
     [28]     P. Hsieh, F. Chong, C. Chang, F. Zheng, K. H. Lin, Bioorg. Med. Chem. Lett., 14, 4751 (2004).
     [29]     K. M. Pritchard, J. A. Rawi, C. Bradley, Eur. J. Med. Chem.,42, 1200 (2007).
     [30]     G. R. Madhavan, R. Chakabarti, R. K. Anantha, M. B. Rajesh, P. B. Rao, R. Rajagopalan, J. Iqbal, Bioorg. Med. Chem.,14, 584 (2006).
     [31]     D. Zhou, B. L. Harrison, U. Shah, T. H. Andree, G. A. Hornby, R. Scerni, L. E. Schechter, D. L. Smith, K. M. Sullivan, R. E. Mewshaw, Bioorg. Med. Chem. Lett.,16, 1338 (2006).
     [32]     U. Neumann, N. Schechter, M. Gutschow, Bioorg. Med. Chem.,9, 947 (2001).
     [33]     E. Colson, J. Wallach, M. Hauteville, Biochimie.,87, 223 (2007).
     [34]     A. Arcadi, C. Asti, L. Brandolini, G. Caseilli, F. Marinelli, V. Ruggieri, Bioorg. Med. Chem. Lett.,9, 1291 (2009).
     [35]     P. W. Hsieh, T. L. Hwang, C. C. Wu, F. R. Chang, T. W. Wang, Y. C. Wu, Bioorg. Med. Chem.,15, 2786 (2005).
     [36]     J. L. Gilmore, S. S. Hay, W. Caprathe, C. Lee, R. Emmering, W. Michael, Bioorg. Med. Chem. Lett.,6, 679 (1966).
     [37]     L. S. Ramesh, S. M. Mahesh, B. W. Jyoti, Internet. J. Pharm. Sci., 4, 320 (2012).
     [38]     N. Taichi, S. Akina, K. Masaki, K. Hashimoto, S. Hiroshi, M. Noboru, W. H. Teruo, W. H. Wakabayashi, Anticancer. Res., 29, 1123 (2009).
     [39]     G. Caliendo, P. Grieco, E. Perisutti, V. Santagada, A. Santini, S. Albrizio, A. Pinto, R. Sorrentino, Eur. J. Med. Chem.,33, 957 (1998).
     [40]     P. Zhang, E. A. Teerfenko, A. Fensome, Z. Zhang, Y. Zhu, J. Cohen, R. Winneker, J. Wrobel, J. Yardley, Bioorg. Med. Chem. Lett.,12, 787 (2002).
     [41]     P. J. Rybczynski, R. E. Zeck, D. W. Combs, I. Turchi, T. P. Burris, J. Z. Xu, M. Yang, K. T. Demarest, Bioorg. Med. Chem. Lett.,13, 2359 (2003).
     [42]     W. Yang, Z. Ma, R. Golla, T. Stouch, R. Seethala, S. Johnson, R. Zhou, T. Gungor, J. H. M. Feyen, J. K. Dickson, Bioorg. Med. Chem. Lett.,14, 2327 (2004).
     [43]     E. Ward, N. Johnson, J. P. Lovell, W. Smith, K. M. Thewlis, A. K. Vong, M. J. Natsonm, Biorg. Med. Chem. Lett.,17, 5214 (2007).
     [44]     S. Deswal, N. Roy, Eur. J. Med. Chem., 41, 552 (2006).
     [45]     M. Ohno, Y. Tanaka, M. Miyamoto, T. Takeda, K. Hoshi, M. Yamada, Biorg. Med. Chem. Lett., 14, 2005 (2006).
     [46]     J. C. Kern, E. A. Terefenko, A. Fensome, R. Unwalla, J. Wrobel, Y. Zhou, J. Cohen, R. Winneker, Z. Zhang, P. Zhang, Bioorg. Med. Chem. Lett.,17, 189 (2007).
     [47]     N. A. Powell, F. L. Ciske, C. Cai, D. D. Holsworth, C. A. Huis, M. Jalaie, J. Day, M. Mastronrdi,  P. McConnell, I. Mochalkin, E. Zhang, M. J. Riyan, J. Bryant, W. Collard, S. Ferriira, C. Gu, R. Collins, J. Edmunds, Bioorg. Med. Chem.,15, 5912 (2007).
     [48]     S. M. Bromidge, B. Bertani, M. Borreiollo, S. Faedo, L. J. Gordon, E. Granci, M. Hill, H. R. Marshal, V. Zucchellli, G. Merco, A. Vesentini, J. M. Watson, L. Zonzini, Bioorg. Med. Chem. Lett.,42, 5653 (2008).
     [49]     N. A. Shakil, A. Pandey, M. K. Singh, J. Kumar, S. K. Awasthi, C. Srivastava, M. K. Singh, P. P. Pandey, J. Environ. Sci. Health. B., 45, 108 (2010).
     [50]     L. Wang, H. Ankati, S. K. Akubathini, M. Balderamos, C. A. Storey, A. V. Patel, V. Price, D. Kretzschmar, E. R. Biehl, S. R. D'Mello, J. Neurosci. Res.,88, 1970 (2010).
     [51]     Z. Dong, Y. Cheng, J. Zhao, L. Su, B. Zhao, Y. Zhang, S. Zhang, J. J. Miao, Cell. Physiol.,1, 202 (2010).