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Research on Chemical Intermediates

, Volume 44, Issue 11, pp 6453–6468 | Cite as

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

  • Malledevarapura Gurumurthy Prabhudeva
  • Karthik Kumara
  • Achutha Dileep Kumar
  • Mylarappa B. Ningappa
  • Neratur K. Lokanath
  • Kariyappa Ajay Kumar
Article

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(ah) by the reaction of 3-methylthiophene-2-carbaldehyde, 1 and acetophenones, 2(ah) by Claisen–Schmidt approach. The chalcones were efficiently transformed into thienyl-pyrazolines, 5(ah) 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(ah) 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.

Keywords

Anti-inflammatory Antimicrobial Chalcone Condensation Carbothioamide 

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

Notes

Acknowledgements

The authors are grateful to the IOE Instrumentation Facility, Vijnana Bhavana, University of Mysore, for recording spectra and X-ray diffraction studies.

Compliance with ethical standards

Conflict of interest

All authors declare no conflict of interest including financial, personal or other relationships with other people or organizations for this article.

Supplementary material

11164_2018_3501_MOESM1_ESM.doc (2.7 mb)
Supplementary material 1 (DOC 2793 kb)

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Malledevarapura Gurumurthy Prabhudeva
    • 1
  • Karthik Kumara
    • 2
  • Achutha Dileep Kumar
    • 1
  • Mylarappa B. Ningappa
    • 3
  • Neratur K. Lokanath
    • 2
  • Kariyappa Ajay Kumar
    • 1
  1. 1.Department of Chemistry, Yuvaraja’s CollegeUniversity of MysoreMysoreIndia
  2. 2.Department of Studies in Physics, ManasagangotriUniversity of MysoreMysoreIndia
  3. 3.Rangos Research CenterUniversity of PittsburghPittsburghUSA

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