Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Antibacterial and Antitubercular Activity of Novel Benzothiazole-Aryl Amine Derivatives Tethered through Acetamide Functionality
Corresponding Author(s) : S. Roshan Salfidoer
Asian Journal of Chemistry,
Vol. 33 No. 8 (2021): Vol 33 Issue 8, 2021
Abstract
A novel series of substituted benzothiazole-N-phenyl acetamides were synthesized through a feasible scheme and characterized by IR, 1H NMR and mass spectral methods. All the synthesized compounds were screened for antibacterial activity against two, Gram-positive strains: Staphylococcus aureus, Bacillus subtilis; four, Gram-negative strains: Escherichia coli, Salmonella typhi, Pseudomonas aeruginosa and Klebsiella pneumonia; and antitubercular activity against mycobacterial strain: Mycobacterium tuberculosis. Among the 15 compounds (6a-o) tested, three compounds 6e, 6l and 6m have demonstrated high potency with MIC values ranges from 6.25-12.5 μg/mL against both Gram-positive and Gram-negative strains. Compounds 6e and 6l displayed remarkable antitubercular activity with MIC value of 25 μg/mL.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- M.J. Cheesman, A. Ilanko, B. Blonk and I.E. Cock, Pharmacogn Rev., 11, 57 (2017); https://doi.org/10.4103/phrev.phrev_21_17
- F.C. Tenover, Clin. Infect. Dis., 33, 108 (2001); https://doi.org/10.1086/321834
- R. Leclercq, Clin. Microbiol. Infect., 15, 224 (2009); https://doi.org/10.1111/j.1469-0691.2009.02739.x
- X. Gao, J. Liu, X. Zuo, X. Feng and Y. Gao, Molecules, 25, 1675 (2020); https://doi.org/10.3390/molecules25071675
- M.S. Vasava, M.N. Bhoi, S.K. Rathwa, D.J. Jethava, P.T. Acharya, D.B. Patel and H.D. Patel, Mini-Rev. Med. Chem., 20, 532 (2020); https://doi.org/10.2174/1389557519666191122125453
- S. Noel, S. Cadet, E. Gras and C. Hureau, Chem. Soc. Rev., 42, 7747 (2013); https://doi.org/10.1039/c3cs60086f
- N.P. Prajapati, R.H. Vekariya, M.A. Borad and H.D. Patel, RSC Adv., 4, 60176 (2014); https://doi.org/10.1039/C4RA07437H
- S.H.L. Kok, R. Gambari, C.H. Chui, M.C.W. Yuen, E. Lin, R.S.M. Wong, F.Y. Lau, G.Y.M. Cheng, W.S. Lam and S.H. Chan, Bioorg. Med. Chem., 16, 3626 (2008); https://doi.org/10.1016/j.bmc.2008.02.005
- Y. Heo, Y.S. Song, B.T. Kim and J.N. Heo, Tetrahedron Lett., 47, 3091 (2006); https://doi.org/10.1016/j.tetlet.2006.02.152
- R.J. Alaimo, S.S. Pelosi and R. Freedman, J. Pharm. Sci., 67, 281 (1978); https://doi.org/10.1002/jps.2600670247
- M. Singh, S.K. Singh, M. Gangwar, G. Nath and S.K. Singh, RSC Adv., 4, 19013 (2014); https://doi.org/10.1039/C4RA02649G
- I. Caleta, M. Grdisa, D. Mrvos-Sermek, M. Cetina, V. Tralic-Kulenovic, K. Pavelic and K. Karminski-Zamola, Il Farmaco, 59, 297 (2004); https://doi.org/10.1016/j.farmac.2004.01.008
- J. Das, R.V. Moquin, J. Lin, C. Liu, A.M. Doweyko, H.F. Defex, Q. Fang, S. Pang, S. Pitt, D.R. Shen, G.L. Schieven, J.C. Barrish and J. Wityak, Bioorg. Med. Chem., 13, 2587 (2003); https://doi.org/10.1016/S0960-894X(03)00511-0
- X. Su, N. Vicker, D. Ganeshapillai, A. Smith, A. Purohit, M.J. Reed and B.V.L. Potter, Mol. Cell. Endocrinol., 248, 214 (2006); https://doi.org/10.1016/j.mce.2005.10.022
- G.M. Sreenivasa, E. Jayachandran, B. Shivakumar, K.K. Jayaraj and K.M.M.J. Vijay, Arch. Pharm. Sci. Res., 1, 150 (2009).
- I. Hutchinson, S.A. Jennings, B.R. Vishnuvajjala, A.D. Westwell and M.F.G. Stevens, J. Med. Chem., 45, 744 (2002); https://doi.org/10.1021/jm011025r
- T.D. Bradshaw and A.D. Westwell, Curr. Med. Chem., 11, 1009 (2004); https://doi.org/10.2174/0929867043455530
- M. Yoshida, I. Hayakawa, N. Hayashi, T. Agatsuma, Y. Oda, F. Tanzawa, S. Iwasaki, K. Koyama, H. Furukawa, S. Kurakata and Y. Sugano, Bioorg. Med. Chem. Lett., 15, 3328 (2005); https://doi.org/10.1016/j.bmcl.2005.05.077
- P. Vicini, A. Geronikaki, M. Incerti, B. Busonera, G. Poni, C.A. Cabras and P. La Colla, Bioorg. Med. Chem., 11, 4785 (2003); https://doi.org/10.1016/S0968-0896(03)00493-0
- S.R. Nagarajan, G.A. De Crescenzo, D.P. Getman, H.-F. Lu, J.A. Sikorski, J.L. Walker, J.J. McDonald, K.A. Houseman, G.P. Kocan, N. Kishore, P.P. Mehta, C.L. Funkes-Shippy and L. Blystone, Bioorg. Med. Chem., 11, 4769 (2003); https://doi.org/10.1016/j.bmc.2003.07.001
- D. Cressier, C. Prouillac, P. Hernandez, C. Amourette, M. Diserbo, C. Lion and G. Rima, Bioorg. Med. Chem., 17, 5275 (2009); https://doi.org/10.1016/j.bmc.2009.05.039
- D.S. Dogruer, S. Unlü, M.F. Sahin and E. Yqilada, Il Farmaco, 53, 80 (1998); https://doi.org/10.1016/S0014-827X(97)00017-7
- M.A. El-Sherbeny, Arzneimittelforschung, 50, 848 (2000); https://doi.org/10.1055/s-0031-1300300
- P. Jimonet, F. Audiau, M. Barreau, J.-C. Blanchard, A. Boireau, Y. Bour, M.-A. Coléno, A. Doble, G. Doerflinger, C. Do Huu, M.-H. Donat, J.M. Duchesne, P. Ganil, C. Guérémy, E. Honoré, R. Kerphirique, B. Just, S. Gontier, P. Hubert, P.M. Laduron, J. Le Blevec, M. Meunier, J.-M. Miquet, C. Nemecek, M. Pasquet, O. Piot, J. Pratt, J. Rataud, M. Reibaud, J.-M. Stutzmann and S. Mignani, J. Med. Chem., 42, 2828 (1999); https://doi.org/10.1021/jm980202u
- N. Siddiqui, A. Rana, S.A. Khan, S.E. Haque, M.S. Alam, W. Ahsan and S. Ahmed, Acta Chim. Slov., 56, 462 (2009).
- B. Rajeeva, N. Srinivasulu and S.M. Shanta Kumar, E-J. Chem., 6, 775 (2009); https://doi.org/10.1155/2009/404596
- R. Danzeisen, B. Schwalenstoecker, F. Gillardon, E. Buerger, V. Krzykalla, K. Klinder, L. Schild, B. Hengerer, A.C. Ludolph, C. DornerCiossek and L. Kussmaul, J. Pharmacol. Exp. Ther., 316, 189 (2006); https://doi.org/10.1124/jpet.105.092312
- B.L. Mylari, E.R. Larson, T.A. Beyer, W.J. Zembrowski, C.E. Aldinger, M.F. Dee, T.W. Siegel and D.H. Singleton, J. Med. Chem., 34, 108 (1991); https://doi.org/10.1021/jm00105a018
- P.D. Beer, M.G.B. Drew, C. Hazlewood, D. Hesek, J. Hodacova and S.E. Stokes, J. Chem. Soc. Chem. Commun., 3, 229 (1993); https://doi.org/10.1039/c39930000229
- P.D. Beer, M.G.B. Drew, D. Hesek and R. Jagessar, J. Chem. Soc. Chem. Commun., 14, 1187 (1995); https://doi.org/10.1039/C39950001187
- P.D. Beer, M.G.B. Drew and R. Jagessar, J. Chem. Soc., Dalton Trans., 21, 881 (1997); https://doi.org/10.1039/a606082j
- R.C. Jagessar and D. Rampersaud, Life Sci. J., 4, 46 (2007).
- R.V. Patel, P.K. Patel, P. Kumari, D.P. Rajani and K.H. Chikhalia, Eur. J. Med. Chem., 53, 41 (2012); https://doi.org/10.1016/j.ejmech.2012.03.033
- E.J. Corey and G. Schmidt, Tetrahedron Lett., 20, 399 (1979); https://doi.org/10.1016/S0040-4039(01)93515-4
- J.R. Dunetz, J. Magano and G.A. Weisenburger, Org. Process Res. Dev., 20, 140 (2016); https://doi.org/10.1021/op500305s
- Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Disc Susceptibility Tests; Approved Standard M2-A9, Clinical and Laboratory Standards Institute, Wayne, PA, USA (2006).
- Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard M7-A7, Clinical and Laboratory Standards Institute, Wayne, PA, USA (2006).
- H.M. Ericsson and J.C. Sherris, Acta Pathol. Microbiol. Scand. B, 217(Suppl.), 217 (1971).
- J.M. Alqahtani and A.M. Asaad, J. Mycobac. Dis., 4, 140 (2014); https://doi.org/10.4172/2161-1068.1000140
References
M.J. Cheesman, A. Ilanko, B. Blonk and I.E. Cock, Pharmacogn Rev., 11, 57 (2017); https://doi.org/10.4103/phrev.phrev_21_17
F.C. Tenover, Clin. Infect. Dis., 33, 108 (2001); https://doi.org/10.1086/321834
R. Leclercq, Clin. Microbiol. Infect., 15, 224 (2009); https://doi.org/10.1111/j.1469-0691.2009.02739.x
X. Gao, J. Liu, X. Zuo, X. Feng and Y. Gao, Molecules, 25, 1675 (2020); https://doi.org/10.3390/molecules25071675
M.S. Vasava, M.N. Bhoi, S.K. Rathwa, D.J. Jethava, P.T. Acharya, D.B. Patel and H.D. Patel, Mini-Rev. Med. Chem., 20, 532 (2020); https://doi.org/10.2174/1389557519666191122125453
S. Noel, S. Cadet, E. Gras and C. Hureau, Chem. Soc. Rev., 42, 7747 (2013); https://doi.org/10.1039/c3cs60086f
N.P. Prajapati, R.H. Vekariya, M.A. Borad and H.D. Patel, RSC Adv., 4, 60176 (2014); https://doi.org/10.1039/C4RA07437H
S.H.L. Kok, R. Gambari, C.H. Chui, M.C.W. Yuen, E. Lin, R.S.M. Wong, F.Y. Lau, G.Y.M. Cheng, W.S. Lam and S.H. Chan, Bioorg. Med. Chem., 16, 3626 (2008); https://doi.org/10.1016/j.bmc.2008.02.005
Y. Heo, Y.S. Song, B.T. Kim and J.N. Heo, Tetrahedron Lett., 47, 3091 (2006); https://doi.org/10.1016/j.tetlet.2006.02.152
R.J. Alaimo, S.S. Pelosi and R. Freedman, J. Pharm. Sci., 67, 281 (1978); https://doi.org/10.1002/jps.2600670247
M. Singh, S.K. Singh, M. Gangwar, G. Nath and S.K. Singh, RSC Adv., 4, 19013 (2014); https://doi.org/10.1039/C4RA02649G
I. Caleta, M. Grdisa, D. Mrvos-Sermek, M. Cetina, V. Tralic-Kulenovic, K. Pavelic and K. Karminski-Zamola, Il Farmaco, 59, 297 (2004); https://doi.org/10.1016/j.farmac.2004.01.008
J. Das, R.V. Moquin, J. Lin, C. Liu, A.M. Doweyko, H.F. Defex, Q. Fang, S. Pang, S. Pitt, D.R. Shen, G.L. Schieven, J.C. Barrish and J. Wityak, Bioorg. Med. Chem., 13, 2587 (2003); https://doi.org/10.1016/S0960-894X(03)00511-0
X. Su, N. Vicker, D. Ganeshapillai, A. Smith, A. Purohit, M.J. Reed and B.V.L. Potter, Mol. Cell. Endocrinol., 248, 214 (2006); https://doi.org/10.1016/j.mce.2005.10.022
G.M. Sreenivasa, E. Jayachandran, B. Shivakumar, K.K. Jayaraj and K.M.M.J. Vijay, Arch. Pharm. Sci. Res., 1, 150 (2009).
I. Hutchinson, S.A. Jennings, B.R. Vishnuvajjala, A.D. Westwell and M.F.G. Stevens, J. Med. Chem., 45, 744 (2002); https://doi.org/10.1021/jm011025r
T.D. Bradshaw and A.D. Westwell, Curr. Med. Chem., 11, 1009 (2004); https://doi.org/10.2174/0929867043455530
M. Yoshida, I. Hayakawa, N. Hayashi, T. Agatsuma, Y. Oda, F. Tanzawa, S. Iwasaki, K. Koyama, H. Furukawa, S. Kurakata and Y. Sugano, Bioorg. Med. Chem. Lett., 15, 3328 (2005); https://doi.org/10.1016/j.bmcl.2005.05.077
P. Vicini, A. Geronikaki, M. Incerti, B. Busonera, G. Poni, C.A. Cabras and P. La Colla, Bioorg. Med. Chem., 11, 4785 (2003); https://doi.org/10.1016/S0968-0896(03)00493-0
S.R. Nagarajan, G.A. De Crescenzo, D.P. Getman, H.-F. Lu, J.A. Sikorski, J.L. Walker, J.J. McDonald, K.A. Houseman, G.P. Kocan, N. Kishore, P.P. Mehta, C.L. Funkes-Shippy and L. Blystone, Bioorg. Med. Chem., 11, 4769 (2003); https://doi.org/10.1016/j.bmc.2003.07.001
D. Cressier, C. Prouillac, P. Hernandez, C. Amourette, M. Diserbo, C. Lion and G. Rima, Bioorg. Med. Chem., 17, 5275 (2009); https://doi.org/10.1016/j.bmc.2009.05.039
D.S. Dogruer, S. Unlü, M.F. Sahin and E. Yqilada, Il Farmaco, 53, 80 (1998); https://doi.org/10.1016/S0014-827X(97)00017-7
M.A. El-Sherbeny, Arzneimittelforschung, 50, 848 (2000); https://doi.org/10.1055/s-0031-1300300
P. Jimonet, F. Audiau, M. Barreau, J.-C. Blanchard, A. Boireau, Y. Bour, M.-A. Coléno, A. Doble, G. Doerflinger, C. Do Huu, M.-H. Donat, J.M. Duchesne, P. Ganil, C. Guérémy, E. Honoré, R. Kerphirique, B. Just, S. Gontier, P. Hubert, P.M. Laduron, J. Le Blevec, M. Meunier, J.-M. Miquet, C. Nemecek, M. Pasquet, O. Piot, J. Pratt, J. Rataud, M. Reibaud, J.-M. Stutzmann and S. Mignani, J. Med. Chem., 42, 2828 (1999); https://doi.org/10.1021/jm980202u
N. Siddiqui, A. Rana, S.A. Khan, S.E. Haque, M.S. Alam, W. Ahsan and S. Ahmed, Acta Chim. Slov., 56, 462 (2009).
B. Rajeeva, N. Srinivasulu and S.M. Shanta Kumar, E-J. Chem., 6, 775 (2009); https://doi.org/10.1155/2009/404596
R. Danzeisen, B. Schwalenstoecker, F. Gillardon, E. Buerger, V. Krzykalla, K. Klinder, L. Schild, B. Hengerer, A.C. Ludolph, C. DornerCiossek and L. Kussmaul, J. Pharmacol. Exp. Ther., 316, 189 (2006); https://doi.org/10.1124/jpet.105.092312
B.L. Mylari, E.R. Larson, T.A. Beyer, W.J. Zembrowski, C.E. Aldinger, M.F. Dee, T.W. Siegel and D.H. Singleton, J. Med. Chem., 34, 108 (1991); https://doi.org/10.1021/jm00105a018
P.D. Beer, M.G.B. Drew, C. Hazlewood, D. Hesek, J. Hodacova and S.E. Stokes, J. Chem. Soc. Chem. Commun., 3, 229 (1993); https://doi.org/10.1039/c39930000229
P.D. Beer, M.G.B. Drew, D. Hesek and R. Jagessar, J. Chem. Soc. Chem. Commun., 14, 1187 (1995); https://doi.org/10.1039/C39950001187
P.D. Beer, M.G.B. Drew and R. Jagessar, J. Chem. Soc., Dalton Trans., 21, 881 (1997); https://doi.org/10.1039/a606082j
R.C. Jagessar and D. Rampersaud, Life Sci. J., 4, 46 (2007).
R.V. Patel, P.K. Patel, P. Kumari, D.P. Rajani and K.H. Chikhalia, Eur. J. Med. Chem., 53, 41 (2012); https://doi.org/10.1016/j.ejmech.2012.03.033
E.J. Corey and G. Schmidt, Tetrahedron Lett., 20, 399 (1979); https://doi.org/10.1016/S0040-4039(01)93515-4
J.R. Dunetz, J. Magano and G.A. Weisenburger, Org. Process Res. Dev., 20, 140 (2016); https://doi.org/10.1021/op500305s
Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Disc Susceptibility Tests; Approved Standard M2-A9, Clinical and Laboratory Standards Institute, Wayne, PA, USA (2006).
Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard M7-A7, Clinical and Laboratory Standards Institute, Wayne, PA, USA (2006).
H.M. Ericsson and J.C. Sherris, Acta Pathol. Microbiol. Scand. B, 217(Suppl.), 217 (1971).
J.M. Alqahtani and A.M. Asaad, J. Mycobac. Dis., 4, 140 (2014); https://doi.org/10.4172/2161-1068.1000140