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Design, Synthesis and Anti-tubercular Evaluation of Some Novel Chroman-Hydrazone Derivatives
Corresponding Author(s) : Kuldeep Singh
Asian Journal of Chemistry,
Vol. 35 No. 2 (2023): Vol 35 Issue 2, 2023
Abstract
The molecular docking, synthesis, spectral characterization and anti-tubercular evaluation of 10 novel N’-substituted-6-hydroxy-2,5,7,8-tetramethylchroman-2-carbohydrazide derivatives (SM1-SM10) were reported. The structures of the synthesized derivatives were affirmed by spectroscopic studies such as FTIR, 1H NMR, 13C NMR and high resolution-mass spectrometry. Predicted ADME and toxicity investigations were accomplished to presume the pharmacokinetic parameters of the compounds. The synthesized compounds were evaluated for in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain using Microplate Alamar Blue Assay (MABA) taking isoniazid, rifampicin, ethambutol, amikacin, streptomycin and levofloxacin as positive drug standards. Compound SM8 has shown the significant anti-tubercular activity among all the titled compounds. The results indicated that chroman-hydrazone skeleton could serve as a lead for the development of novel anti-tubercular drugs.
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- WHO, Global Tuberculosis Control a Short Update to the 2019 Report, World Health Organization, Geneva (2019); https://www.who.int/tb/publications/global_report/en/
- C. Sacchettini, E.J. Rubin and J.S. Freundlich, Nat. Rev. Microbiol., 6, 41 (2008); https://doi.org/10.1038/nrmicro1816
- M.V. De Souza, Recent Patents Anti-Infect. Drug Disc., 1, 33 (2006); https://doi.org/10.2174/157489106775244163
- M.V. De Souza, Curr. Opin. Pulm. Med., 12, 167 (2006); https://doi.org/10.1097/01.mcp.0000219264.42686.c9
- F. Annunziata, C. Pinna, S. Dallavalle, L. Tamborini and A. Pinto, Int. J. Mol. Sci., 21, 4618 (2020); https://doi.org/10.3390/ijms21134618
- K. Upadhyay, A. Bavishi, S. Thakrar, A. Radadiya, H. Vala, S. Parekh, D. Bhavsar, M. Savant, M. Parmar, P. Adlakha and A. Shah, Bioorg. Med. Chem. Lett., 21, 2547 (2011); https://doi.org/10.1016/j.bmcl.2011.02.016
- A.H. Rezayan, P. Azerang, S. Sardari and A. Sarvary, Chem. Biol. Drug Des., 80, 929 (2012); https://doi.org/10.1111/cbdd.12044
- E. Pini, G. Poli, T. Tuccinardi, L.R. Chiarelli, M. Mori, L. Costantino, A. Gelain, S. Villa, F. Meneghetti and D. Barlocco, Molecules, 23, 1506 (2018); https://doi.org/10.3390/molecules23071506
- C. Loncle, J.M. Brunel, N. Vidal, M. Dherbomez and Y. Letourneux, Eur. J. Med. Chem., 39, 1067 (2004); https://doi.org/10.1016/j.ejmech.2004.07.005
- S.K. Sridhar, S.N. Pandeya, J.P. Stables and A. Ramesh, Eur. J. Pharm. Sci., 16, 129 (2002); https://doi.org/10.1016/S0928-0987(02)00077-5
- S.G. Küçükgüzel, A. Mazi, F. Sahin, S. Öztürk and J.P. Stables, Eur. J. Med. Chem., 38, 1005 (2003); https://doi.org/10.1016/j.ejmech.2003.08.004
- A.R. Todeschini, A.L.P. de Miranda, K.C.M. da Silva, S.C. Parrini and E.J. Barreiro, Eur. J. Med. Chem., 33, 189 (1998); https://doi.org/10.1016/S0223-5234(98)80008-1
- S. Eswaran, A.V. Adhikari, N.K. Pal and I.H. Chowdhury, Bioorg. Med. Chem. Lett., 20, 1040 (2010); https://doi.org/10.1016/j.bmcl.2009.12.045
- K.K. Bedia, O. Elcin, U. Seda, K. Fatma, S. Nathaly, R. Sevim and A. Dimoglo, Eur. J. Med. Chem., 41, 1253 (2006); https://doi.org/10.1016/j.ejmech.2006.06.009
- J. Vinsová, A. Imramovský, J. Jampílek, J.F. Monreal and M. Dolezal, Anti-Infect. Agents Med. Chem., 7, 12 (2008); https://doi.org/10.2174/187152108783329780
- A. Nayyar, A. Malde, E. Coutinho and R. Jain, Bioorg. Med. Chem., 14, 7302 (2006); https://doi.org/10.1016/j.bmc.2006.06.049
- A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
- J. Eberhardt, D. Santos-Martins, A.F. Tillack and S. Forli, J. Chem. Inf. Model., 61, 3891 (2021); https://doi.org/10.1021/acs.jcim.1c00203
- O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/jcc.21334
- D.S. Biovia, Discovery Studio Modeling Environment, Dassault Syst. Release, San Diego, USA (2017).
- S.M. Batt, T. Jabeen, V. Bhowruth, L. Quill, P.A. Lund, L. Eggeling, L.J. Alderwick, K. Fütterer and G.S. Besra, Proc. Natl. Acad. Sci. USA, 109, 11354 (2012); https://doi.org/10.1073/pnas.1205735109
- L.J. Alderwick, G.S. Lloyd, H. Ghadbane, J.W. May, L. Eggeling, A. Bhatt, K. Fütterer and G.S. Besra, PLoS Pathog., 7, e1001299 (2011); https://doi.org/10.1371/journal.ppat.1001299
- J.A. Hyatt, Synth. Commun., 38, 8 (2007); https://doi.org/10.1080/00397910701648728
- P. Rawat and S.M. Verma, Drug Des. Devel. Ther., 10, 2779 (2016); https://doi.org/10.2147/DDDT.S111266
- M.C.S. Lourenço, M.V.N. Souza, A.C. Pinheiro, M.L. Ferreira, R.S.B. Gonçalves, T.C.M. Nogueira and M.A. Peralta, ARKIVOC, 181 (2007); https://doi.org/10.3998/ark.5550190.0008.f18
References
WHO, Global Tuberculosis Control a Short Update to the 2019 Report, World Health Organization, Geneva (2019); https://www.who.int/tb/publications/global_report/en/
C. Sacchettini, E.J. Rubin and J.S. Freundlich, Nat. Rev. Microbiol., 6, 41 (2008); https://doi.org/10.1038/nrmicro1816
M.V. De Souza, Recent Patents Anti-Infect. Drug Disc., 1, 33 (2006); https://doi.org/10.2174/157489106775244163
M.V. De Souza, Curr. Opin. Pulm. Med., 12, 167 (2006); https://doi.org/10.1097/01.mcp.0000219264.42686.c9
F. Annunziata, C. Pinna, S. Dallavalle, L. Tamborini and A. Pinto, Int. J. Mol. Sci., 21, 4618 (2020); https://doi.org/10.3390/ijms21134618
K. Upadhyay, A. Bavishi, S. Thakrar, A. Radadiya, H. Vala, S. Parekh, D. Bhavsar, M. Savant, M. Parmar, P. Adlakha and A. Shah, Bioorg. Med. Chem. Lett., 21, 2547 (2011); https://doi.org/10.1016/j.bmcl.2011.02.016
A.H. Rezayan, P. Azerang, S. Sardari and A. Sarvary, Chem. Biol. Drug Des., 80, 929 (2012); https://doi.org/10.1111/cbdd.12044
E. Pini, G. Poli, T. Tuccinardi, L.R. Chiarelli, M. Mori, L. Costantino, A. Gelain, S. Villa, F. Meneghetti and D. Barlocco, Molecules, 23, 1506 (2018); https://doi.org/10.3390/molecules23071506
C. Loncle, J.M. Brunel, N. Vidal, M. Dherbomez and Y. Letourneux, Eur. J. Med. Chem., 39, 1067 (2004); https://doi.org/10.1016/j.ejmech.2004.07.005
S.K. Sridhar, S.N. Pandeya, J.P. Stables and A. Ramesh, Eur. J. Pharm. Sci., 16, 129 (2002); https://doi.org/10.1016/S0928-0987(02)00077-5
S.G. Küçükgüzel, A. Mazi, F. Sahin, S. Öztürk and J.P. Stables, Eur. J. Med. Chem., 38, 1005 (2003); https://doi.org/10.1016/j.ejmech.2003.08.004
A.R. Todeschini, A.L.P. de Miranda, K.C.M. da Silva, S.C. Parrini and E.J. Barreiro, Eur. J. Med. Chem., 33, 189 (1998); https://doi.org/10.1016/S0223-5234(98)80008-1
S. Eswaran, A.V. Adhikari, N.K. Pal and I.H. Chowdhury, Bioorg. Med. Chem. Lett., 20, 1040 (2010); https://doi.org/10.1016/j.bmcl.2009.12.045
K.K. Bedia, O. Elcin, U. Seda, K. Fatma, S. Nathaly, R. Sevim and A. Dimoglo, Eur. J. Med. Chem., 41, 1253 (2006); https://doi.org/10.1016/j.ejmech.2006.06.009
J. Vinsová, A. Imramovský, J. Jampílek, J.F. Monreal and M. Dolezal, Anti-Infect. Agents Med. Chem., 7, 12 (2008); https://doi.org/10.2174/187152108783329780
A. Nayyar, A. Malde, E. Coutinho and R. Jain, Bioorg. Med. Chem., 14, 7302 (2006); https://doi.org/10.1016/j.bmc.2006.06.049
A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
J. Eberhardt, D. Santos-Martins, A.F. Tillack and S. Forli, J. Chem. Inf. Model., 61, 3891 (2021); https://doi.org/10.1021/acs.jcim.1c00203
O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/jcc.21334
D.S. Biovia, Discovery Studio Modeling Environment, Dassault Syst. Release, San Diego, USA (2017).
S.M. Batt, T. Jabeen, V. Bhowruth, L. Quill, P.A. Lund, L. Eggeling, L.J. Alderwick, K. Fütterer and G.S. Besra, Proc. Natl. Acad. Sci. USA, 109, 11354 (2012); https://doi.org/10.1073/pnas.1205735109
L.J. Alderwick, G.S. Lloyd, H. Ghadbane, J.W. May, L. Eggeling, A. Bhatt, K. Fütterer and G.S. Besra, PLoS Pathog., 7, e1001299 (2011); https://doi.org/10.1371/journal.ppat.1001299
J.A. Hyatt, Synth. Commun., 38, 8 (2007); https://doi.org/10.1080/00397910701648728
P. Rawat and S.M. Verma, Drug Des. Devel. Ther., 10, 2779 (2016); https://doi.org/10.2147/DDDT.S111266
M.C.S. Lourenço, M.V.N. Souza, A.C. Pinheiro, M.L. Ferreira, R.S.B. Gonçalves, T.C.M. Nogueira and M.A. Peralta, ARKIVOC, 181 (2007); https://doi.org/10.3998/ark.5550190.0008.f18