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.
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Abbreviations
- TLC:
-
Thin layer chromatography
- CCD:
-
Charge couple device
- CIF:
-
Crystallographic information file
- CCDC:
-
Cambridge Crystallographic Data Centre
- NMR:
-
Nuclear magnetic resonance
- UPLC:
-
Ultimate performance liquid chromatography
- ESI:
-
Electrospray
- APCI:
-
Atmospheric pressure chemical ionization
- MTCC:
-
Microbial type culture collection
- VRV-PL-8a:
-
Vipera russelli (Russell’s viper) snake venom phospholipase A2
- RFU:
-
Relative Fluorescence Unit
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Acknowledgements
The authors are grateful to the IOE Instrumentation Facility, Vijnana Bhavana, University of Mysore, for recording spectra and X-ray diffraction studies.
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Prabhudeva, M.G., Kumara, K., Dileep Kumar, A. et al. Amberlyst-15 catalyzed synthesis of novel thiophene–pyrazoline derivatives: spectral and crystallographic characterization and anti-inflammatory and antimicrobial evaluation. Res Chem Intermed 44, 6453–6468 (2018). https://doi.org/10.1007/s11164-018-3501-2
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DOI: https://doi.org/10.1007/s11164-018-3501-2