Synthesis and Biological Screening of New 2-(5-Aryl-1-phenyl-1 H-pyrazol-3-yl)-4-aryl Thiazole Derivatives as Potential Antimicrobial Agents

Yogesh Nandurkar; Abhijit Shinde; Manish R Bhoye; Shivaji Jagadale; Pravin Chimaji Mhaske

doi:10.1021/acsomega.2c08137

Synthesis and Biological Screening of New 2-(5-Aryl-1-phenyl-1 H-pyrazol-3-yl)-4-aryl Thiazole Derivatives as Potential Antimicrobial Agents

ACS Omega. 2023 Feb 22;8(9):8743-8754. doi: 10.1021/acsomega.2c08137. eCollection 2023 Mar 7.

Authors

Yogesh Nandurkar^{1

2}, Abhijit Shinde¹, Manish R Bhoye^{1

3}, Shivaji Jagadale⁴, Pravin Chimaji Mhaske¹

Affiliations

¹ Post-Graduate Department of Chemistry, S. P. Mandali's Sir Parashurambhau College, Tilak Road, Pune 411030, India.
² Department of Chemistry, Nowrosjee Wadia College, Pune 411001, India.
³ Department of Chemistry, S.N. Arts, D.J.M. Commerce and B.N.S. Science College, Sangamner 422605, District Ahmednagar, India.
⁴ Department of Chemistry, S.K. Gandhi Arts, Amolak Science and P.H. Gandhi Commerce College Kada, Tal. Ashti 414202, District Beed, India.

Abstract

A new series of 2-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl thiazoles (10a-ab) have been synthesized by a cyclocondensation reaction of 5-aryl-1-phenyl-1H-pyrazole-3-carbothioamide (7a-d) with substituted phenacyl bromide (8a-f). The structure of newly synthesized 2-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl thiazole (10a-ab) derivatives was characterized by spectroscopic analysis. The compounds 10a-ab were evaluated for in vitro antibacterial activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388), Bacillus subtilis (NCIM 2063), Staphylococcus aureus (NCIM 2178), and in vitro antifungal activity against Aspergillus niger (ATCC 504) and Candida albicans (NCIM 3100). Among the twenty-eight pyrazolyl-thiazole derivatives, six compounds, 10g, 10h, 10i, 10j, 10o, and 10t, showed good activity against P. mirabilis; four compounds 10q, 10u, 10y, and 10z showed good activity against S. aureus; and twenty-four derivatives showed good antifungal activity against A. niger. Compounds 10g, 10q, 10r, 10s, and 10ab showed comparable activity with respect to the reference drug Ravuconazole. Thus, the significant antimicrobial activity of 2-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl thiazole (10a-ab) derivatives prompted that these scaffolds could assist in the development of lead compounds to treat microbial infections.