Amberlyst-15 catalyzed synthesis of novel thiophene–pyrazoline derivatives: spectral and crystallographic characterization and anti-inflammatory and antimicrobial evaluation
| Autor: | Kariyappa Ajay Kumar, Mylarappa Ningappa, Neratur Krishnappagowda Lokanath, Karthik Kumara, Achutha Dileep Kumar, M. G. Prabhudeva |
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| Rok vydání: | 2018 |
| Předmět: |
biology
010405 organic chemistry Aspergillus niger Aspergillus flavus General Chemistry Bacillus subtilis 010402 general chemistry biology.organism_classification Antimicrobial 01 natural sciences 0104 chemical sciences Catalysis chemistry.chemical_compound Acetic acid chemistry Thiophene Acetonitrile Nuclear chemistry |
| Zdroj: | Research on Chemical Intermediates. 44:6453-6468 |
| ISSN: | 1568-5675 0922-6168 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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