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Synthesis, Characterization and in vitro Antitubercular Evaluation of Some Schiff Bases of Substituted Indoles and their Inclusion Complexes with b-Cyclodextrin
Corresponding Author(s) : Bamakanta Garnaik
Asian Journal of Chemistry,
Vol. 30 No. 3 (2018): Vol 30 Issue 3
Abstract
Indole derivatives are best known for their biological importance as bactericides and fungicides which encouraged us to synthesize some Schiff bases of substituted indoles i.e. 2(([1,3,4]thiadiazino[6,5-b]indol-3-ylimino)methyl)substituted phenols. The synthesized compounds are found to exhibit antitubercular activities. With a view to enhance solubility induced potential anti tubercular activities, these synthesized compounds are encapsulated with b-cyclodextrin. Through elemental and spectral (UV, IR, 1H NMR) characterization, the architecture of the compounds and their inclusion complexes are confirmed. They are also screened for in vitro antitubercular activities by using rifampicin as the reference standard. The synthesized compounds exhibited good antitubercular activity but their inclusion complexes exhibited profound antitubercular activities as compared to their respective compounds.
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- D.S. Mehta, K.H. Sikotra and H.V. Shah, Indian J. Chem., 44B, 2594 (2005).
- H. Panwar, N. Chaudhary and S. Singh, Rasayan J. Chem., 4, 371 (2011).
- N.V. Cinchana, P.S. Sujan Ganapathy and S.D. Shruthi, Res. J. Pharm. Biol. Chem. Sci., 2, 353 (2011).
- M. Tichy, R. Pohl, H.Y. Xu, Y. Chen, F. Yokokawa, P.-Y. Shi and M. Hocek, Bioorg. Med. Chem., 20, 6123 (2012); https://doi.org/10.1016/j.bmc.2012.08.021.
- S. Lingala, R. Nerella, R. Cherukupally and A.K. Das, Int. J. Pharm. Sci. Rev. Res., 6, 128 (2011).
- B.C. Hong, Y. Jiang, Y. Chang and S. Lee, J. Chin. Chem. Soc. (Taipei), 53, 647 (2006); https://doi.org/10.1002/jccs.200600086.
- E. Nassar, J. Am. Sci. Org., 6, 338 (2010).
- G.P. Kalaskar, M. Girisha, M.G. Purohit, B.S. Thippeswamy and B.M. Patil, Indian J. Heterocycl. Chem., 16, 325 (2007).
- P.K. Das, R. Sahu and B.K. Garnaik, IOSR J. Appl. Chem., 9, 2265 (2016).
- B. Yang, J. Lin, Y. Chen and Y. Liu, Bioorg. Med. Chem., 17, 6311 (2009); https://doi.org/10.1016/j.bmc.2009.07.060.
- J. Szetjli, TIBTRCH, 7, 171 (1989).
- S. Panda and J.K. Tripathy, Asian J. Chem., 23, 1631 (2011).
- R. Sahu, P.K. Das and B. Garnaik, Pharmachem, 8, 176 (2016).
- T. Higuchi and K.A. Connor, Adv. Anal. Chem. Instrum., 4, 117 (1965).
- S.S. Nayak, S. Panda, P. Panda and M.S. Padhy, Bulg. Chem. Commun., 42, 147 (2010).
- H.A. Benesi and J.H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1994); https://doi.org/10.1021/ja01176a030.
- C. Mamatha, M. Thangavel and V. Beaulah, Eur. J. Pharm. Med. Res., 3, 382 (2016).
- S. Hazra and G.S. Kumar, RSC Advances, 5, 1873 (2015); https://doi.org/10.1039/C4RA10204E.
- J. Szetli, ed.: W.F. Smolen and L.A. Ball, Controlled Drug Bioavailability, Wiley Interscience, New York, vol. 3, 365 (1985).
- C. Nicolescu, C. Arama, A. Nedelcu and C.M. Monciu, Farmacia, 58, 78 (2010).
References
D.S. Mehta, K.H. Sikotra and H.V. Shah, Indian J. Chem., 44B, 2594 (2005).
H. Panwar, N. Chaudhary and S. Singh, Rasayan J. Chem., 4, 371 (2011).
N.V. Cinchana, P.S. Sujan Ganapathy and S.D. Shruthi, Res. J. Pharm. Biol. Chem. Sci., 2, 353 (2011).
M. Tichy, R. Pohl, H.Y. Xu, Y. Chen, F. Yokokawa, P.-Y. Shi and M. Hocek, Bioorg. Med. Chem., 20, 6123 (2012); https://doi.org/10.1016/j.bmc.2012.08.021.
S. Lingala, R. Nerella, R. Cherukupally and A.K. Das, Int. J. Pharm. Sci. Rev. Res., 6, 128 (2011).
B.C. Hong, Y. Jiang, Y. Chang and S. Lee, J. Chin. Chem. Soc. (Taipei), 53, 647 (2006); https://doi.org/10.1002/jccs.200600086.
E. Nassar, J. Am. Sci. Org., 6, 338 (2010).
G.P. Kalaskar, M. Girisha, M.G. Purohit, B.S. Thippeswamy and B.M. Patil, Indian J. Heterocycl. Chem., 16, 325 (2007).
P.K. Das, R. Sahu and B.K. Garnaik, IOSR J. Appl. Chem., 9, 2265 (2016).
B. Yang, J. Lin, Y. Chen and Y. Liu, Bioorg. Med. Chem., 17, 6311 (2009); https://doi.org/10.1016/j.bmc.2009.07.060.
J. Szetjli, TIBTRCH, 7, 171 (1989).
S. Panda and J.K. Tripathy, Asian J. Chem., 23, 1631 (2011).
R. Sahu, P.K. Das and B. Garnaik, Pharmachem, 8, 176 (2016).
T. Higuchi and K.A. Connor, Adv. Anal. Chem. Instrum., 4, 117 (1965).
S.S. Nayak, S. Panda, P. Panda and M.S. Padhy, Bulg. Chem. Commun., 42, 147 (2010).
H.A. Benesi and J.H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1994); https://doi.org/10.1021/ja01176a030.
C. Mamatha, M. Thangavel and V. Beaulah, Eur. J. Pharm. Med. Res., 3, 382 (2016).
S. Hazra and G.S. Kumar, RSC Advances, 5, 1873 (2015); https://doi.org/10.1039/C4RA10204E.
J. Szetli, ed.: W.F. Smolen and L.A. Ball, Controlled Drug Bioavailability, Wiley Interscience, New York, vol. 3, 365 (1985).
C. Nicolescu, C. Arama, A. Nedelcu and C.M. Monciu, Farmacia, 58, 78 (2010).