Issue

Vol. 30 No. 12 (2018): Vol 30 Issue 12

Copyright (c) 2018 AJC

Creative Commons License

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

Synthesis Characterization and Biological Evaluation of Some Novel Amino Pyrazole Derivatives

https://doi.org/10.14233/ajchem.2018.21499
Nilay Shah
Department of Chemistry, Kadi Sarva Vishwavidyalaya, Gandhinagar-382 024, India
Pineshkumar N. Patel
Huntsman International India Pvt Ltd, Vadodara-391 440, India
Denish C. Karia
Department of Chemistry, Patel J.D.K. Davolwala Science College, Borsad-388 540, India

Corresponding Author(s) : Nilay Shah

nilayashah315@rediffmail.com

Asian Journal of Chemistry, Vol. 30 No. 12 (2018): Vol 30 Issue 12

Abstract

Amino pyrazole and their derivatives for their biological activities. Present work describes the synthesis of novel amino pyrazole derivatives and evaluation of their medicinal value. The reaction of 3,5-bis(trifluoromethyl)aniline with cyanoacetic acid in presence of ethylene dichloride-hydrochloride produced N-[3,5-bis(trifluoromethyl)phenyl]-2-cyanoacetamide (1); this intermediate, upon further reaction with dimethyl sulfide in presence of K2CO3 followed by reaction with methyl iodide was converted to N-[3,5-bis(trifluoromethyl)phenyl]-2-cyano-3,3-bis(methylthio)acrylamide (2). The cyclization of 2 with hydrazine in isopropyl alcohol resulted in 3-amino-N-[3,5- bis(trifluoromethyl)phenyl]-5-(methylthio)-1H-pyrazole-4-carboxamide (3) as main scaffold. This isolated scaffold finally reacted with various derivatives of aldehyde followed by reduction with sodium borohydride to isolate target compounds AP-1 to AP-17. The structures of the synthesized compounds were confirmed by mass, FT-IR and 1H NMR analysis. All the compounds were tested for potential antifungal and antimicrobial activity. Out of 17 compounds AP-1, 3, 4, 7, 9, 10 and 11 compounds having good activity in antimicrobial agent.

Keywords

Pyrazole Amine derivatives Carboxamide derivatives Antimicrobial Antifungal activity
Shah, N., Patel, P. N., & Karia, D. C. (2018). Synthesis Characterization and Biological Evaluation of Some Novel Amino Pyrazole Derivatives. Asian Journal of Chemistry, 30(12), 2647–2651. https://doi.org/10.14233/ajchem.2018.21499
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. D.S. Jain and P.C. Sharma, Acta Pol. Pharm. Drug Res., 67, 63 (2010).
  2. Khalid Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y.N. Mabkhot, F.A. Al-Aizari and M. Ansar, Molecules, 23, 134 (2018); https://doi.org/10.3390/molecules23010134.
  3. B. Kocyigit-Kaymakcioglu, H.Z. Toklu, S. Ikiz, A.F. Bagcigil, S. Rollas, N.Y. Ozgur and A.K. Seyyal, J. Enzyme Inhib. Med. Chem., 23, 454 (2008) https://doi.org/10.1080/14756360701631686.
  4. R. Galici, J. Pharmacol. Exp. Ther., 318, 173 (2006); https://doi.org/10.1124/jpet.106.102046.
  5. D.S. Jain, P.C. Sharma, P. Verma, M. Kumar and C.P. Dora, Acta Pol. Pharm. Drug Res., 67, 225 (2010).
  6. A. Madhkar, N. Kannappan, A. Deep, P. Kumar, M. Kumar and P. Verma, Int. J. Chemtech Res., 1, 1376 (2009).
  7. C.X. Wei, M. Bian and G.H. Gong, Molecules, 20, 5528 (2015); https://doi.org/10.3390/molecules20045528.
  8. J.J. Liu, M.Y. Zhao, X. Zhang, X. Zhao and H.L. Zhu, Mini Rev. Med. Chem., 13, 1957 (2013); https://doi.org/10.2174/13895575113139990078.
  9. M.S. Mohamed, R. El-Domany and R. Abd El-Hameed, Acta Pharm., 59, 145 (2009); https://doi.org/10.2478/v10007-009-0016-9.
  10. H. Patil, D. Varadaraji, S.S. Suban, V.R. Ramasamy, K. Kubendiran, J.S. K.G. Raguraman and S.K. Nalilu, Org. Commun., 3, 45 (2010).
  11. S.J. Chao, X.P. Hui, S. Li, Z.Z. Qiu, P.F. Xu, Z.Y. Zhang, Q. Wang and Z.W. Guan, J. Chin. Chem. Soc., 52, 539 (2005); https://doi.org/10.1002/jccs.200500079.
  12. A.A. Bekhit, O.A. el-Sayed, E. Aboulmagd and J.Y. Park, Eur. J. Med. Chem., 39, 249 (2004); https://doi.org/10.1016/j.ejmech.2003.12.005.
  13. U. Natarajan, I. Kaliappan and N.K. Singh, Der Pharma Chem., 2, 159 (2010).
  14. A. Rajasekaran and P.P. Thampi, Eur. J. Med. Chem., 39, 273 (2004); https://doi.org/10.1016/j.ejmech.2003.11.016.
  15. C.N.S.S.P. Kumar, D.K. Parida, A. Santhoshi, A.K. Kota, B. Sridhar and V.J. Rao, MedChemComm, 2, 486 (2011); https://doi.org/10.1039/c0md00263a.
  16. V.H. Bhaskar and P.B. Mohite, J. Optoelectronics Biomed. Mater., 2, 249 (2010).
  17. S.B. Wang, X.Q. Deng, Y. Zheng, Y.P. Yuan, Z.S. Quan and L.P. Guan, Eur. J. Med. Chem., 56, 139 (2012); https://doi.org/10.1016/j.ejmech.2012.08.027.
  18. X.Y. Sun, C.X. Wei, X.Q. Deng, Z.-G. Sun and Z.-S. Quan, Pharmacol. Rep., 62, 273 (2010); https://doi.org/10.1016/S1734-1140(10)70266-8.
  19. J. Wu, Q. Wang, J. Guo, Z. Hu, Z. Yin, J. Xu and X. Wu, Eur. J. Pharmacol., 589, 220 (2008); https://doi.org/10.1016/j.ejphar.2008.05.007.
  20. S. Sharma, M.C. Sharma and D.V. Kohli, J. Optoelectron. Biomed. Mater., 1, 151 (2008).
  21. S. Rao and K.S. Babu, Org. Commun., 4, 105 (2011).
  22. J.H. Kim, J.H. Lee, S.H. Paik, J.H. Kim and Y.H. Chi, Arch. Pharm. Res., 35, 1123 (2012); https://doi.org/10.1007/s12272-012-0700-z.
  23. A. Rajasekaran and A.K. Rajagopal, Acta Pharm., 59, 355 (2009); https://doi.org/10.2478/v10007-009-0026-7.
  24. Y.L. Gao, G.L. Zhao, W. Liu, H. Shao, Y.L. Wang, W.R. Xu, L.D. Tang and J.W. Wang, Indian J. Chem., 49B, 1499 (2010).
  25. K. Pegklidou, C. Koukoulitsa, I. Nicolaou and V.J. Demopoulos, Bioorg. Med. Chem., 18, 2107 (2010); https://doi.org/10.1016/j.bmc.2010.02.010.
  26. A. Sharon, R. Pratap, P. Tiwari, A. Srivastava, P.R. Maulik and V.J. Ram, Bioorg. Med. Chem. Lett., 15, 2115 (2005); https://doi.org/10.1016/j.bmcl.2005.02.060.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0