Article Sidebar

Download
PDF

Main Article Content

Abstract

A novel series of benzene sulfonamide pyrazole linked [1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole derivatives have been synthesized by reaction of 4-(3-(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-5- (3-fluoro-4-methoxyphenyl)-1H-pyrazol-1-yl)benzenesulfonamide with different substituted benzoic/ pyridinyl/indolyl acids in POCl3, characterized by IR, 1H NMR, 13C NMR, MS analytical data and evaluated for their antibacterial as well as antifungal activity. Antibacterial activity of compounds 6c, 6i and 6k were found good against E. coli, P. aeruginosa, S. aureus and S. pyogenes compared to standard ampicillin. Compounds 6b and 6e is having promising antifungal activity against C. albicans as compare to standard griseofulvin.

Keywords

Acid hydrazide Benzene sulfonamide pyrazole Antibacterial activity Antifungal activity 4-amino-1,2,4-triazole-3-thiol, triazolo-thiadiazole

Article Details

How to Cite
M. Shingare, R., S. Patil, Y., S. Gadekar, S., P. Rajani, D., & R. Madje, B. (2018). Synthesis and Antimicrobial Evaluation of Novel Benzene Sulfonamide Pyrazole Linked [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole Derivatives. Asian Journal of Organic & Medicinal Chemistry, 3(3), 75–80. https://doi.org/10.14233/ajomc.2018.AJOMC-P106
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX

References

  1. S.C. Holm and B.F. Straub, Synthesis of N-Substituted 1,2,4-Triazoles. A Review, Org. Prep. Proced. Int., 43, 319 (2011); https://doi.org/10.1080/00304948.2011.593999.
  2. S. Desai, U. Laddi, R. Bennur and S. Bennur, Synthesis and Anti-microbial Activities of Some New 1,2,4-Triazole Derivatives, Indian J. Chem., 52B, 1176 (2013).
  3. S. Swamy, B. Basappa, B.S. Priya, B. Prabhuswamy, B.H. Doreswamy, J.S. Prasad and K.S. Rangappa, Synthesis of Pharmaceutically Important Condensed Heterocyclic 4,6-Disubstituted-1,2,4-Triazolo-1,3,4-Thiadiazole Derivatives as Antimicrobials, Eur. J. Med. Chem., 41, 531 (2006); https://doi.org/10.1016/j.ejmech.2005.12.009.
  4. M. Akhter, M. Hassan and M. Amir, Synthesis and Pharmacological Evaluation of 3-Diphenylmethyl-6-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles: A Condensed Bridgehead Nitrogen Heterocyclic System, Arab. J. Chem., 7, 955 (2014); https://doi.org/10.1016/j.arabjc.2014.05.036.
  5. N. Chidananda, B. Poojary, V. Sumangala, N.S. Kumari, P. Shetty and T. Arulmoli, Facile Synthesis, Characterization and Pharmacological Activities of 3,6-Disubstituted 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles and 5,6-Dihydro-3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles, Eur. J. Med. Chem., 51, 124 (2012); https://doi.org/10.1016/j.ejmech.2012.02.030.
  6. A. Husain, M. Rashid, R. Mishra, S. Parveen, D. Shin and D. Kumar, Benzimidazole Bearing Oxadiazole and Triazolo-Thiadiazoles Nucleus: Design and Synthesis as Anticancer Agents, Bioorg. Med. Chem. Lett., 22, 5438 (2012); https://doi.org/10.1016/j.bmcl.2012.07.038.
  7. S. El-Khawass, M. Khalil, A. Hazzaa, H. Bassiouny and N. Loutfy, Synthesis of Some 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles as Potential Anthelmintics, Farmaco, 44, 703 (1989).
  8. Y.A. Al-Soud, N.A. Al-Masoudi, R. Loddo and P. La Colla, in vitro Anti-HIV and Antitumor Activity of New 3,6-Disubstituted [1,2,4]triazolo-[3,4-b][1,3,4]thiadiazoles and Thiadiazine Analogues, Arch. Pharm., 341, 365 (2008); https://doi.org/10.1002/ardp.200700272.
  9. M. Karthikeyan, B. Holla, B. Kalluraya and N. Kumari, Biological Studies of Some 2,4-Dichloro-5-fluorophenyl Containing Triazolothia-diazoles, Monatsh. Chem., 138, 1309 (2007); https://doi.org/10.1007/s00706-007-0718-y.
  10. R. Shingare, Y. Patil, S. Gadekar, J. Sangshetti and B. Madje, Synthesis and Antibacterial Screening of Novel 1,3,5-Triaryl-4, 5-dihydro-1H-pyrazole Derivatives, Moroc. J. Chem., 5, 177 (2017).
  11. H.A. Abdel-Aziz, K.A. Al-Rashood, K.E.H. ElTahir and G.M. Suddek, Synthesis of N-benzenesulfonamide-1H-pyrazoles Bearing Arylsulfonyl Moiety: Novel Celecoxib Analogs as Potent Anti-Inflammatory Agents, Eur. J. Med. Chem., 80, 416 (2014); https://doi.org/10.1016/j.ejmech.2014.04.065.
  12. P. Khloya, P. Kumar, A. Mittal, N.K. Aggarwal and P.K. Sharma, Synthesis of Some Novel 4-Arylidene Pyrazoles as Potential Antimicrobial Agents, Org. Med. Chem. Lett., 3, 9 (2013); https://doi.org/10.1186/2191-2858-3-9.
  13. A.A. Bekhit, H.M.A. Ashour, A.E.-D.A. Bekhit, H.M. Abdel-Rahman and S.A. Bekhit, Synthesis of Some Pyrazolyl Benzenesulfonamide Derivatives as Dual Anti-Inflammatory Antimicrobial Agents, J. Enzyme Inhib. Med. Chem., 24, 296 (2009); https://doi.org/10.1080/14756360802188404.
  14. H.S. Ibrahim, S.M. Abou-Seri, M. Tanc, M.M. Elaasser, H.A. Abdel-Aziz and C.T. Supuran, Isatin-Pyrazole Benzenesulfonamide Hybrids Potently Inhibit Tumor-Associated Carbonic Anhydrase Isoforms IX And XII, Eur. J. Med. Chem., 103, 583 (2015); https://doi.org/10.1016/j.ejmech.2015.09.021.
  15. T. Rogez-Florent, S. Meignan, C. Foulon, P. Six, A. Gros, C. Bal-Mahieu, C.T. Supuran, A. Scozzafava, R. Frederick, B. Masereel, P. Depreux, A. Lansiaux, J.F. Goossens, S. Gluszok and L. Goossens, New Selective Carbonic Anhydrase IX Inhibitors: Synthesis and Pharmacological Evaluation of Diarylpyrazole-Benzenesulfonamides, Bioorg. Med. Chem., 21, 1451 (2013); https://doi.org/10.1016/j.bmc.2012.10.029.
  16. P.M. Hawkey and D.A. Lewis, Medical Bacteriology-A Practical Approach, Oxford University Press, United Kingdom (1994).
  17. H.N. Raundal, R.P. Jadhav, A.A. Patil and V.D. Bobade, Synthesis and Biological Screening of Novel Pyrazole and Isoxazole Derivatives, Indian J. Chem., 54B, 979 (2015).
  18. H.N. Raundal, R.P. Jadhav, A.A. Patil and V.D. Bobade, Synthesis and Biological Activity of Novel Derivatives of 2-(5-(3-Fluro-4-methoxy phenyl)-1H-pyrazol-3-yl)-5-aryl-1,3,4-oxadiazole, Indian J. Chem., 55B, 892 (2016).
  19. A. Cansiz, A. Cetin, P. Kutulay and M. Koparir, Synthesis of Tautomeric Forms of 5-(2-Hydroxyphenyl)-4-substituted-3H-1,2,4-triazole-3-thione, Asian J. Chem., 21, 617 (2009).
  20. S. Ozturk, M. Akkurt, A. Cansiz, M. Koparir, M. Sekerci, F.W. Heinemann, 4-(4-Chloro­phenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione, Acta Cryst., E60, o425 (2004); https://doi.org/10.1107/S1600536804003721.