Amberlyst-15 catalyzed synthesis of novel thiophene–pyrazoline derivatives: Spectral and crystallographic characterization and anti-inflammatory and antimicrobial evaluation

Prabhudeva, M. G. and Karthik Kumara and Dileep Kumar, A. and Ningappa, M. B. and Lokanath, N. K. and Ajay Kumar, K. (2018) Amberlyst-15 catalyzed synthesis of novel thiophene–pyrazoline derivatives: Spectral and crystallographic characterization and anti-inflammatory and antimicrobial evaluation. Research on Chemical Intermediates, 44 (11). pp. 6453-6468. ISSN 1568-5675

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Official URL: https://doi.org/10.1007/s11164-018-3501-2

Abstract

Increasing instances of antimicrobial drug resistance and Inflammation-mediated disorders requires the design and synthesis of new small-molecules with higher affinity and specificity for their potential targets to serve as antibiotics or anti-inflammatory drugs, respectively. The current study presents the synthesis of a series of chalcones, 3(a–h) by the reaction of 3-methylthiophene-2-carbaldehyde, 1 and acetophenones, 2(a–h) by Claisen–Schmidt approach. The chalcones were efficiently transformed into thienyl-pyrazolines, 5(a–h) by their reaction with thiosemicarbazide hydrochloride, 4 in the presence of Amberlyst-15 as a catalyst in acetonitrile at room temperature. Alternatively, the compounds 5(a–h) were prepared by conventional method using acetic acid (40%) medium. Structures were characterized by spectral and single crystal X-ray diffraction studies. Preliminary assessment of the anti-inflammatory properties of the compounds showed that, amongst the series, compounds 5b and 5c have excellent anti-inflammatory activities. Further, compound 5c showed excellent activity against Escherichia coli (MIC, 15 µg/mL), Bacillus subtilis (MIC, 20 µg/mL), Aspergillus niger (MIC, 20 µg/mL), and Aspergillus flavus (MIC 15 µg/mL), respectively. Compounds 5a and 5b were also found to be active against the tested microorganisms.

Item Type: Article
Subjects: C Chemical Science > Chemistry
D Physical Science > Physics
Divisions: Yuvaraj college > Chemistry
Depositing User: manjula User
Date Deposited: 05 Jul 2019 05:06
Last Modified: 05 Jul 2019 05:06
URI: http://eprints.uni-mysore.ac.in/id/eprint/4607

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