Issue

Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022

Copyright (c) 2022 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization and Biological Screening of Novel Imidazolylpyrazole Scaffolds

https://doi.org/10.14233/ajchem.2022.23570
Jyotsna Sharma
Department of Chemistry, Maharishi Markandeshwar University, Sadopur-Ambala-134007, India
Hardeep Singh Tuli
Department of Biotechnology, Maharishi Markandeshwar (Deemed to be)University, Mullana-Ambala-133207, India
Mayank Kinger
Department of Chemistry, Chaudhary Bansi Lal University, Bhiwani-127021, India
Ram Pal
R&D, SRF Limited, Chemicals Technology Group, Tijara-301019, India
Zahoor Abbas
Department of Chemistry, Maharishi Markandeshwar University, Sadopur-Ambala-134007, India
Manoj Kumar
Department of Chemistry, Maharishi Markandeshwar University, Sadopur-Ambala-134007, India

Corresponding Author(s) : Manoj Kumar

manojraju27@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022

Abstract

A novel series of 3-(4-aryl)-4-(4,5-diphenyl-1H-imidazol-2-yl)-1-phenyl-1H-pyrazole was synthesized by employing the well-known Debus-Radziszewski reaction. Structures of all the newly synthesized compounds have been characterized by various spectroscopic techniques viz. FTIR, 1H and 13C NMR, LC-MS and elemental analysis. All these compounds were also screened for antimicrobial potential against bacterial strains of S. aureus, K. pneumoniae and fungal strains of A. niger and T. rubrum.

Keywords

Heterocycles Vilsmeier-Haack reaction Imidazolylpyrazole hybrids Benzil Antimicrobial activity
Sharma, J., Singh Tuli, H., Kinger, M., Pal, R., Abbas, Z., & Kumar, M. (2022). Synthesis, Characterization and Biological Screening of Novel Imidazolylpyrazole Scaffolds. Asian Journal of Chemistry, 34(3), 614–618. https://doi.org/10.14233/ajchem.2022.23570
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. B. Ardiansah, Asian J. Pharm. Clin. Res., 10, 45 (2017); https://doi.org/10.22159/ajpcr.2017.v10i12.22065
  2. R. Alam, D. Wahi, R. Singh, D. Sinha, V. Tandon, A. Grover and Rahisuddin, Bioorg. Chem., 69, 77 (2016); https://doi.org/10.1016/j.bioorg.2016.10.001
  3. J.K. Sony and S. Ganguly, Int. J. Pharm. Pharm. Sci., 8, 75 (2016); https://doi.org/10.22159/ijpps.2016v8i11.12634
  4. A.A. Bekhit, A.M.M. Hassan, H.A. Abd El Razik, M.M.M. El-Miligy, E.J. El-Agroudy and A.E.-D.A. Bekhit, Eur. J. Med. Chem., 94, 30 (2015); https://doi.org/10.1016/j.ejmech.2015.02.038
  5. V. Michon, C.H. du Penhoat, F. Tombret, J.M. Gillardin, F. Lepage and L. Berthon, Eur. J. Med. Chem., 30, 147 (1995); https://doi.org/10.1016/0223-5234(96)88220-1
  6. D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice and M.E. Feigenson, J. Med. Chem., 28, 256 (1985); https://doi.org/10.1021/jm00380a020
  7. A. Mathew, T.L. Mary Sheeja, T. Arun Kumar, K. Radha, Hygeia J. D. Med., 3, 48 (2011).
  8. H. Kumar, K.K. Bansal and A. Goyal, Anti-Infective Agents, 18, 207 (2020); https://doi.org/10.2174/2211352517666191022103831
  9. F. Nikhath and I.A.K. Mohammed, Chem. Sci. Trans., 3, 450 (2014); https://doi.org/10.7598/cst2014.588
  10. M. Khoobi, F. Ghanoni, H. Nadri, A. Moradi, M. Pirali Hamedani, F.H. Moghadam, S. Emami, M. Vosooghi, R. Zadmard, A. Foroumadi and A. Shafiee, Eur. J. Med. Chem., 89, 296 (2015); https://doi.org/10.1016/j.ejmech.2014.10.049
  11. S. Mert, Z. Alim, M.M. Isgör, B. Anil, R. Kasimogullari and S. Beydemir, Arab. J. Chem., 12, 2740 (2019); https://doi.org/10.1016/j.arabjc.2015.05.020
  12. Y.R. Li, C. Li, J.C. Liu, M. Guo, T.Y. Zhang, L.P. Sun, C.J. Zheng and H.R. Piao, Bioorg. Med. Chem. Lett., 25, 5052 (2015); https://doi.org/10.1016/j.bmcl.2015.10.028
  13. A.A. Estrada, B.K. Chan, C. Baker-Glenn, A. Beresford, D.J. Burdick, M. Chambers, H. Chen, S.L. Dominguez, J. Dotson, J. Drummond, M. Flagella, R. Fuji, A. Gill, J. Halladay, S.F. Harris, T.P. Heffron, T. Kleinheinz, D.W. Lee, C.E.L. Pichon, X. Liu, J.P. Lyssikatos, A.D. Medhurst, J.G. Moffat, K. Nash, K. Scearce-Levie, Z. Sheng, D.G. Shore, S. Wong, S. Zhang, X. Zhang, H. Zhu and Z.K. Sweeney, J. Med. Chem., 57, 921 (2014); https://doi.org/10.1021/jm401654j
  14. R.H. Wiley and P. Wiley, Pyrazolones, Pyrazolidones and Derivatives, John Wiley and Sons, New York, p. 102 (1964).
  15. A. Jamwal, A. Javed and V. Bhardwaj, J. Pharm. BioSci., 3, 114 (2013);
  16. S.T. Heller and S.R. Natarajan, Org. Lett., 8, 2675 (2006); https://doi.org/10.1021/ol060570p
  17. M. Kinger, J. Sharma, M. Kumar, R. Bala, V. Kumar and V. Prakash, Indian J. Heterocycl. Chem., 30, 341 (2020).
  18. V. Satyanarayana and A. Sivakumar, Chem. Pap., 65, 519 (2011); https://doi.org/10.2478/s11696-011-0028-z
  19. A.J. Carrilo-Muñoz, C. Tur, J. Torres and A.C. Seymour, J. Antimicrob. Chemother., 37, 815 (1996); https://doi.org/10.1093/jac/37.4.815
  20. H. Che, T.N. Tuyen, H.P. Kim and H. Park, Bioorg. Med. Chem. Lett., 20, 4035 (2010); https://doi.org/10.1016/j.bmcl.2010.05.092
  21. P. Zhan, X. Liu, J. Zhu, Z. Fang, Z. Li, C. Pannecouque and E.D. Clercq, Bioorg. Med. Chem., 17, 5775 (2009); https://doi.org/10.1016/j.bmc.2009.07.028
  22. R. Kitbunnadaj, O.P. Zuiderveld, B. Christophe, S. Hulscher, W.M. Menge, E. Gelens, E. Snip, R.A. Bakker, S. Celanire, M. Gillard, P. Talaga, H. Timmerman and R. Leurs, J. Med. Chem., 47, 2414 (2004); https://doi.org/10.1021/jm049932u
  23. C.A. Valdez, J.C. Tripp, Y. Miyamoto, J. Kalisiak, P. Hruz, Y.S. Andersen, S.E. Brown, K. Kangas, L.V. Arzu, B.J. Davids, F.D. Gillin, J.A. Upcroft, P. Upcroft, V.V. Fokin, D.K. Smith, K.B. Sharpless and L. Eckmann, J. Med. Chem., 52, 4038 (2009); https://doi.org/10.1021/jm900356n
  24. D. Pectasides, H. Yianniotis, N. Alevizakos, D. Bafaloukos, V. Barbounis, J. Varthalitis, M. Dimitriadis and A. Athanassiou, Br. J. Cancer, 60, 627 (1989); https://doi.org/10.1038/bjc.1989.327
  25. L. Salerno, M.N. Modica, G. Romeo, V. Pittalà, M.A. Siracusa, M.E. Amato, R. Acquaviva, C. Di Giacomo and V. Sorrenti, Eur. J. Med. Chem., 49, 118 (2012); https://doi.org/10.1016/j.ejmech.2012.01.002
  26. K. Anand and S. Wakode, Int. J. Chem. Biol., 5, 350 (2017).
  27. G.K. Sharma and D. Pathak, Chem. Pharm. Bull., 58, 375 (2010); https://doi.org/10.1248/cpb.58.375
  28. M.W. Bhade and P.R. Rajput, Int. J. Appl. Pure Sci. Agric., 2, 80 (2016)
  29. A.S. Salman, A. Abdel-Aziem and M. J. Alkubbat, Am. J. Org. Chem., 5, 57 (2015); https://doi.org/10.5923/j.ajoc.20150502.01
  30. B. Behmaram, N. Foroughifar, N. Foroughifar and S. Hallajian, Int. J. Chem., 9, 45 (2017); https://doi.org/10.5539/ijc.v9n2p45
  31. R. Ganapathi and A. Krishan, Cancer Res., 40, 1103 (1980).
  32. J.C. Pelling and C. Shipman Jr., Biochem. Pharmacol., 25, 2377 (1976); https://doi.org/10.1016/0006-2952(76)90031-9
  33. A.M. Vijesh, A.M. Isloor, S. Telkar, S.K. Peethambar, S. Rai and N. Isloor, Eur. J. Med. Chem., 46, 3531 (2011); https://doi.org/10.1016/j.ejmech.2011.05.005
  34. D. Zampieri, M.G. Mamolo, E. Laurini, G. Scialino, E. Banfi and L. Vio, Bioorg. Med. Chem., 16, 4516 (2008); https://doi.org/10.1016/j.bmc.2008.02.055
  35. P.N. Kalaria, S.P. Satasia and D.K. Raval, Eur. J. Med. Chem., 78, 207 (2014); https://doi.org/10.1016/j.ejmech.2014.02.015
  36. K. Sato, T. Kawagishi and H. Kobayashi, Silver Halide Color Photo-graphic Material, Tech. Rep., JP 07134380 (1995).
  37. H. Brahmbhatt, M. Molnar and V. Pavic, Karbala Int. J. Mod. Sci., 4, 200 (2018); https://doi.org/10.1016/j.kijoms.2018.01.006
  38. F. Hatamjafari and H. Khojastehkouhi, Orient. J. Chem., 30, 329 (2014); https://doi.org/10.13005/ojc/300143
  39. S. Punia, V. Verma, D. Kumar, A. Kumar, L. Deswal and M. Parshad, Synth. Commun., 51, 2832 (2021); https://doi.org/10.1080/00397911.2021.1953532
  40. G. Arora, S. Sharma and S. Joshi, Asian J. Chem., 29, 1651 (2017); https://doi.org/10.14233/ajchem.2017.20423
  41. P. Rajput and S. S. Rajput, Int. J. Pharm. Pharm. Sci., 3, 346 (2011),
  42. K. Singh, S. Ralhan, P.K. Sharma and S.N. Dhawan, J. Chem. Res., 316 (2005); https://doi.org/10.3184/0308234054323959
  43. R.P. Saini, V. Kumar, A.K. Gupta and G.K. Gupta, Med. Chem. Res., 23, 690 (2014); https://doi.org/10.1007/s00044-013-0657-6
  44. M. Kumar, H.S. Pallvi, H.S. Tuli and R. Khare, Asian J. Chem., 31, 799 (2019); https://doi.org/10.14233/ajchem.2019.21732
  45. F. Chaudhry, S. Naureen, M. Aslam, M. Al-Raashida, J. Rahman, R. Huma, J. Fatima, M. Khan, M.A. Munawar and M.A. Khan, ChemistrySelect, 5, 11817 (2020); https://doi.org/10.1002/slct.202002482
  46. F. Chaudhry, S. Naureen, M. Ashraf, M. Al-Rashida, B. Jahan, M.A. Munawar and M.A. Khan, Bioorg. Chem., 82, 267 (2019); https://doi.org/10.1016/j.bioorg.2018.10.047
  47. B. Khameneh, M. Iranshahy, V. Soheili and B.S. Fazly Bazzaz, Antimicrob. Resist. Infect. Control, 8, 118 (2019); https://doi.org/10.1186/s13756-019-0559-6
  48. G.P. Bodey, Clin. Infect. Dis., 14, 161 (1992); https://doi.org/10.1093/clinids/14.Supplement_1.S161
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0