Synthesis, Characterization and Biological Activities of Pyrazole Based Heterocycles

Nitin V. Kale, Supriya P. Salve, Bhaskar H. Zaware, Bhausaheb K. Karale, Anil E. Athare, Sushama B. Dare and Sushama J. Takate*,

Department of Chemistry, New Arts, Commerce and Science College (Affiliated to Savitribai Phule Pune University, Pune), Ahmednagar-414001, India

*Corresponding author: Fax: + 91 241 2324715; E-mail: sjtakate26@gmail.com

Abstract

In this work, a unique pyrazolyl compounds comprising flourine and thiophene were synthesized. In brief, esters 3a-f were synthesized by reacting thiophene and pyrazolyl acid (1) with various 2-hydroxyacetophenones (2a-f). The 1,3-diketones 4a-f were formed by Baker-Venkataraman rearrangement of esters 3a-f. Compounds 4a-f were cyclized to form chromene derivatives 5a-f, which further converted into pyrazolyl derivatives 6a-f. The majority of the compounds in series 3a-f, 4a-f, 5a-f and 6a-f showed promising antibacterial activity against S. typhii, S. aureus, B. subtilis and E. coli. Compounds 4e and 4f exhibited considerable antifungal activity against A. niger, while the majority of the compounds had promising activity against T. viride. At 1 mg/mL concentration, some of the synthesized compounds shown potential α-amylase inhibitory action.

Keywords

Baker-Venkataraman rearrangement, Chromone, Pyrazole, Antimicrobial activity.

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