Synthesis, characterization and biological activities of Schiff bases derived from 2-hydroxy-3-nitrobenzaldehyde

doi:10.5246/jcps.2017.12.096

Abstract

Abstract:

Four novel Schiff bases were synthesized by the condensation reaction of 2-hydroxyl-3-nitrobenzaldehyde with either benzothiazoles or benzimidazolamines. The compounds 1–4 were characterized by spectroscopic and analytical methods. The crystal structures of 6-methoxy-1,3-benzothiazol-2-amine and compound 2 are reported only. The 6-methoxy-1,3-benzothiazol-2-amine was found to crystallize in the orthorhombic crystal system in the space group Pbca, having eight molecules in the unit cell, while compound 2 was found to crystallize in the monoclinic crystal system in the space group P2₁/c.The biological activities of these compounds were investigated by evaluating their antibacterial, antifungal, antimalarial, anti-HIV and anti-trypanosomiasis activities. These compounds displayed very interesting antibacterial, antifungal, antimalarial, anti-trypanosomiasis, anti-HIV and low cytotoxicity activity against HeLa cells.

Key words: Schiff bases, Biological activity, Synthesis, X-ray diffraction Characterization

CLC Number:

R916

Supporting:

Monisola Itohan Ikhile, Marthe Carine Djuidje Fotsing, Charmaine Arderne, Jane Catherine Ngila, Derek Tantoh Ndinteh. Synthesis, characterization and biological activities of Schiff bases derived from 2-hydroxy-3-nitrobenzaldehyde[J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(12): 858-871.

References

[1] Arulmurugan, S.; Kavitha, H.P.; Venkatraman, B.R. Rasayan J. Chem. 2010, 3, 385-410.

[2] Qin, W.; Long, S.; Panunzio, M.; Biondi, S. Molecules. 2013, 18, 12264-12289.

[3] Desai, S.B.; Dessai, P.B.; Desai, K.R. Heterocycl. Commun. 2001, 7, 83-90.

[4] Przybylski, P.; Huczynski, A.; Pyta, K.; Brzezinski, B.; Bartl, F. Curr. Org. Chem. 2009, 13, 124-148.

[5] Rathelot, P.; Vanelle, P.; Gasquet, M.; Delmas, F.; Crozet, M.P.; Timon-David, P.; Maldonado, J. Eur. J. Med. Chem. 1995, 30, 503-508.

[6] De Souza, A.O.; Galetti, F.C.S.; Silva, C.L.; Bicalho, B.; Pharma, M.M.; Fonseca, S.F.; Marsaioli, A.J.; Trindade, A.C.L.B.; Freitas-Gil, R.P.; Bezerra, F.S. Nova. 2007, 30, 1563-1566.

[7] Kumar, S.; Dhar, D.N.; Saxena, P.N. J. Sci. Ind. Res. 2009, 68, 181-187.

[8] Wu, Z.S.; Lu, Z.P.; Yen, Z.H. Trans. Met. Chem. 1993, 18, 291-294.

[9] Silva da, C.; Silva da, D.; Modolo, L.; Alves R. J. Ad. Res. 2011, 2, 1-8.

[10] Brodowska, K.; Lodyga-Chruscinska, E. Chemik. 2014, 68, 129-134.

[11] Asobo, P.F.; Wahe, H.; Mbafor, J.T.; Nkengfack, A.E.; Fomum, Z.T.; Sopbue, E.F.; Dopp, D. J. Chem. Soc., Perkin Trans. 2001, 1, 457-461.

[12] Pandeya, S.; Sriram, D.; Nath, G.; de Clercq, E. IL Farmaco. 1999, 54, 624-628.

[13] Padalkar, V.S.; Borse, B.N.; Gupta, V.D.; Phatangare, K.R.; Patil, V.S.; Umape, P.G.; Sekar, N. Arab. J. Chem. 2012, 6, 319-326.

[14] Ali, R.; Siddiqui, N. J. Chem. 2013, 1-12.

[15] Naveen, K.T.; Sai, K.B.; Chandana, K. J. basic appl. Res. 2016, 2, 226-231.

[16] Souza, P.; Garcia-Vazquez, J.A.; Masaguer, J.R. Transition Met. Chem. 1985, 10, 410-412.

[17] Gupta, S.R.; Mourya, P.; Singh, M.M.; Singh, V.P. J. Organomet. Chem. 2014, 767, 136-143.

[18] Motswainyana, W.M.; Onani, M.O.; Madiehe, A.M. Polyhedron. 2012, 41, 44-51.

[19] Ikhile, M.I.; Ngila, J.C. Chin. J. Inorg. Chem. 2015, 31, 2079-2088.

[20] Yousif, E.; Majeed, A.; Al-Sammarrae, K.; Salih, N.; Salimon, J.; Abdullah, B. Arab. J. Chem. 2013, http://dx.doi.org/10.1016/j.arabjc.2013.06.006.

[21] Annapoorani, S.; Krishnan, C. J. ChemTech. Res. 2013, 5, 180-185.

[22] Salimon, J.; Salih, N.; Ibraheem, H.; Yousif, E. Asian J. Chem. 2010, 22, 5289-5296.

[23] Gaber, K.; Mabrouk, H.; Al-Shihrt, S. Egypt. J. Chem. 2001, 44, 191-200.

[24] Rana, A.; Siddiqui, N.; Khan, S.A. Indian J. Pharm. Sci. 2007, 69, 10-17.

[25] Bruker-AXS, APEX2, SADABS, and SAINT Software Reference Manuals. Bruker-AXS, Madison, Wisconsin, USA, 2009.

[26] Sheldrick, G.M. Acta Cryst. 2008, 64, 112-122.

[27] Spek, A.L. Acta Crystallogr. 1997, 30, 565.

[28] Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339-341.

[29] Farrugia L.J. J. Appl. Crystallogr. 1997, 30, 565.

[30] Grobler, J.A.; Stillmock, K.; Hu, B.; Witmer, M.; Felock, P.; Espeseth, A.S.;Wolfe, A.; Egbertson, M.; Bourgeois, M.; Melamed, J. Proc. Natl. Acad. Sci. USA. 2002, 99, 6661-6666.

[31] Lam, T.L.; Lam, M.L.; Au, T.K.; Ip, D.T.M.; Ng, T.B.; Fong, W.P. Wan, D.C.C. Life Sci. 2000, 67, 2889-2896.

[32] Zaheer, M.; Shah, A.; Akhter, Z.; Qureshi, R.; Mirza, B.; Tauseef, M.; Bolte, M. Appl. Organometal. Chem. 2011, 25, 61-69.

[33] Bruno, I.J.; Cole, J.C.; Kessler, M.; Jie Luo, W.D.S.M.; Purkis, L.H.; Smith, B.R.; Taylor, R.; Cooper, R.I.; Harris, S.E.; Orpen, A.G. Chem. Inform. Compu. Sci. 2004, 44, 2133-2144.

[34] Raman, N.; Raja, S.J.; Sakthivel, A. J. Coord. Chem. 2009, 62, 691-705.

[35] Eskandari, M.; Haghighi, N.; Ahmadi, V.; Haghighi, F.; Mohammadi, S.H.R. Physica B. 2011, 406, 112-114.

[36] Sharma, M.; Chauhan, K.; Srivastava, R.K.; Singh, S.V.; Srivastava, K.; Saxena, J.K.; Puri, S.K.; Chauhan, P.M.S. Chem. Biol. Drug Des. 2014, 84, 175-181.

[37] Garg, G.; Acharya, A.; Patel, K. IJPSR. 2013, 4, 3588-3595.

[38] Navarro, M.; Gabbiani, C.; Messori, L.; Gambino, D. Drug Discov. Today. 2010, 15, 1070-1078.

[39] Haque, M.M.; Kudrat-E-Zahan, M.D.; Banu, L.A; Islam, M.D.S.; Islam, M.S. Bioinorg. Chem. Applic. 2015, 1-7.
[40] Kumar, S.; Dhar, D.N.; Saxena, P.N. J. Scientific Industrial. Res. 2009, 68, 181-189.