Synthesis and antimycobacterial evaluation of new 1-substituted benzyl-4-(1-phenyl-3-substituted phenyl-1H-pyrazol-4-yl)-1H-1,2,3-triazole Derivatives

Authors

  • Pravin Mhaske  Post Graduate, Department of Chemistry, S. P. Mandali’s Sir Parashurambhau College, Tilak Road, Pune, India (Affiliated to Savitribai Phule Pune University)
  • Shivaji Jagdale  Department of Chemistry, Smt .S. K.Gandhi Arts and. Amolak Science, and P H Gandhi Commerce College, Kada, Dist. Beed, Indi
  • Abhijit Shinde  Post Graduate, Department of Chemistry, S. P. Mandali’s Sir Parashurambhau College, Tilak Road, Pune, India (Affiliated to Savitribai Phule Pune University)
  • Vivek Bobade  Post Graduate Department of Chemistry, H P T Arts and RYK Science College, Nashik, India (Affiliated to Savitribai Phule Pune University)

Keywords:

1,2,3-Triazole, Pyrazole, Antitubercular Activity, Antibacterial Activity

Abstract

A new series of 1-substituted benzyl-4-(1-phenyl-3-substituted phenyl-1H-pyrazol-4-yl)-1H-1,2,3-triazole derivatives, 5a-k have been synthesized. The structure of the newly synthesized compounds was determined by spectral analysis. The title compounds were screened for their preliminary antitubercular activity against Mycobacterium tuberculosis H37Ra active and dormant (MTB, ATCC 25177) and antimicrobial activity against standard Gram-negative bacteria, Escherichia coli (NCIM 2576), Pseudomonas flurescence (NCIM 2059) and Gram-positive bacteria, Staphylococcus aureus (NCIM 2602), Bacillus subtilis (NCIM 2162). Most of the synthesized compounds reported moderate activity against M. tuberculosis H37Ra and Bacillus subtilis strains.

References

  1. World Health Organization, Tuberculosis Fact Sheet. (2016)
  2. R. Ramesh, R. D. Shingare, V. Kumar, A. Anand, B. Swetha, S. Veeraraghavan, S. Viswanadha, R. Ummanni, R. Gokhale, D.S. Reddy, 2016, Eur. J.Med. Chem. 122, 723.
  3. V.U. Jeankumar, S.R. Rudraraju, R. Vats, R. Janupally, S. Saxena, P. Yogeeswari, D. Sriram, 2016; Eur. J. Med. Chem.? 122, 216.
  4. H.N. Hafez, H.A. Abbas, A.R. El-Gazzar, 2008, Acta Pharm. 58, 359.
  5. A. Passannanti, P. Diana, P. Barraja, F. Mingooia, A. Lauria, G. Cirrincine, 1998, Heterocycles? 48, 1229.
  6. L.P. Guan, Q.H. Jin, G.R. Tian, K.Y. Chai, Z.S. Quan, 2007, J. Pharm. Sci. 10, 254.
  7. S. Manfredini, C.B. Vicentini, M. Manfrini, N. Bianchi, C. Rustigliano, C. Mischiati, R. Gambari, 2000, Bioorg. Med. Chem. 8, 2343.
  8. V. Dmitry, A.V. Demchuk, N.B. Samet, V.I. Chernysheva, G.A. Ushkarov, L. D. Stashina, M.M. Konyushkin, S.I. Raihstat, A.A. Firgang, M.P. Philchenkov, L.M. Zavelevich, V.F. Kuiava, D.Y. Chekhun, A.S. Blokhin, M.N. Kiselyov, V.V. Semenova, 2014, Bioorg. Med. Chem. 22, 738.
  9. S.C. Beasley, N. Cooper, L. Gowers, J.P. Gregory, A.A.F. Haughan, P.G. Hellewell, D. Macar, J. Miotla, J.G. Montana, T. Morgan, R. Taylor, K.A. Runcie, B. Tuladhar, J.B.H. Warneck, 1998, Bioorg. Med. Chem. Lett. 8, 2629.
  10. C. E. De, 1997, Clin. Microbiol. Rev. 10, 674.
  11. T. Weide, S.A. Saldanha, D. Minond, T.P. Spicer, J.R. Fotsing, M. Spaargaren, J. Frere, C. Bebrone, K.B. Sharpless, P.S. Hodder, V.V. Fokin, 2010, ACS Med. Chem. Lett. 1, 150
  12. N.B. Patel, I.H. Khan, S.D. Rajani, 2010, Eur. J. Med. Chem. 45, 4293.
  13. G.R. Jadhav, M.U. Shaikh, R.P. Kale, M.R. Shiradkar, C.H. Gill, 2009, Eur. J. Med. Chem. 44, 2930
  14. D. Castagnolo, M. Radi, F. Dessi, F. Manetti, M. Saddi, R. Meleddu, A.D. Logu, M. Botta, 2009, Bioorg. Med. Chem. Lett. 19, 2203.
  15. S.R. Patpi, L. Pulipati, P. Yogeeswari, D. Sriram, N. Jain, B. Sridhar, R. Murthy A.T., Devi, S.V. Kalivendi, S. Kantevari, 2012, J. Med. Chem. 55, 3911.
  16. M.H. Shaikh, D.D. Subhedar, L. Nawale, D. Sarkar, F.A. Kalam Khan, J.N. Sangshetti, B.B. Shingate 2015, Med. Chem Comm. 6, 1104.
  17. P. Shanmugavelan, S. Nagarajan, M. Sathishkumar, A. Ponnuswamy, P. Yogeeswari, D. Sriram, 2011, Bioorg.? Med. Chem.? Lett. 21, 7273.
  18. S. R. Patpi, L. Pulipati, P. Yogeeswari, D. Sriram, N. Jain, B. Sridhar, R. Murthy, T. Anjana Devi, S. V. Kalivendi, S. Kantevari, 2012, J. Med. Chem. 55, 3911.
  19. G. Turan-Zitouni, M. S?vac?, F. S. K?l?c, K. Erol, 2001, Eur. J. Med. Chem. 36, 685.
  20. A. A. Bekhit, H. T. Y. Fahmy, 2003, Arch. Pharm. Pharm. Med. Chem. 2. 111.
  21. E. Banoglu, C. Akoglu, S. Unlu, E. Kupeli, E. Yesilada, M.F. Sahin, 2004, Arch. Pharm.Pharm. Med. Chem. 337, 7.
  22. S. A. M. El-Hawash, E. A. M. Badawey, I. M. El-Ashmawy, 2006, Eur. J. Med. Chem. 41, 155.
  23. O. Rosati, M. Curini, M. C. Marcotullio, A. Macchiarulo, M. Perfumi, L. Mattioli,F. Rismondo, G. Cravotto, 2007, Bioorg. Med. Chem. 15, 3463.
  24. G. Szabo, J. Fischer, A. Kis-Varga, K. GyiRes, 2008, J. Med. Chem. 51, 142.
  25. N. Benaamane, B. Nedjar-Kolli, Y. Bentarzi, L. Hammal, A. Geronikaki,P. Eleftheriou, A. Lagunin, 2008, Bioorg. Med. Chem. 6, 3059.
  26. R. C. Khunt, V. M. Khedkar, R. S. Chawda, N. A. Chauhan, A. R. Parikh, E. C. Coutinho 2012, Bioorg. Med. Chem. Lett. 22, 666?678
  27. Kumar, S.; Bawa, S.; Drabu, S.; Kumar, R.; Gupta, H. 2009, Recent Pat. Antiinfect Drug Discov. 4, 154.
  28. T. Taj, R. R. Kamble, T. M. Gireesh, R. K. Hunnur, S. B. Margankop, 2011, Eur. J. Med.Chem. 46, 4366.
  29. M. Kira, Z. Nofal, K. Z. Gadalla, 1970, Tetrahedron Lett. 48, 4215.
  30. A. Khan, D. Sarkar, 2008, J. Microbiol. Methods 73, 62.
  31. R. Singh, L. Nawale, M.? Arkile, U. Shedbalkar, S. Wadhwani, D. Sarkar, B. Chopade, 2015, Int. J. Antimicrob. Agents 46, 183.
  32. S. Sarkar, D. Sarkar, 2012, J. Biomol.Screening, 17, 966.
  33. U. Singh, S. Akhtar, A. Mishra, D. Sarkar, 2011, J. Microbiol. Methods 84, 202.
  34. A. Khan, S.? Sarkar, D. Sarkar, 2008, Int. J. Antimicrob. Agents, 32, 40.
  35. T. Mosmann, 1983, J. Immunol. Methods. 65, 55.

International Journal of Scientific Research in Science and Technology

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Published

2017-12-15

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Volume 3, Issue 9, November-December-2017

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Research Articles

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[1]
Pravin Mhaske, Shivaji Jagdale, Abhijit Shinde, Vivek Bobade, " Synthesis and antimycobacterial evaluation of new 1-substituted benzyl-4-(1-phenyl-3-substituted phenyl-1H-pyrazol-4-yl)-1H-1,2,3-triazole Derivatives , International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 3, Issue 9, pp.215-221, November-December-2017.