Synthesis, Spectral Characterization, Molecular Docking Studies, and
Biological Evaluation of Pyranoquinolinyl Acrylic Acid (PQAA)
Diastereomers as Antibacterial Agents Promoted by Indium (III) Triflate
in 1-Butyl-3-Methylimidazolium Tetrafluoroborate Ionic Liquid
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Published:2024-07-26
Issue:
Volume:21
Page:
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ISSN:1570-1786
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Container-title:Letters in Organic Chemistry
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language:en
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Short-container-title:LOC
Author:
venkatapathy K.1,
Magesh C. J.1
Affiliation:
1. PG & Research Department of Chemistry, Arignar Anna Govt. Arts and Science College Cheyyar, Tamilnadu, India
Abstract
In the present investigation, we report the multistep synthesis of pyranoquinolinyl acrylic
acid (PQAA)/furoquinolinyl acrylic acid (FQAA) diastereomers via perkin condensation and reduction,
followed by one-pot inverse electron demand Diels-Alder reaction among 2,3 dihydropyran,
amine, and aromatic aldehyde mediated by indium (III) triflate in 1-butyl-3-methylimidazolium tetrafluoroborate
(In(OTf)3/ [bmim]BF4) at 25.0-27.0oC. The pyranoquinolinyl acrylic acid/furoquinolinyl
acrylic acid diastereomers were evaluated for their in vitro antibacterial activity. Molecular docking
studies were carried out employing iGEMDOCK software to evaluate the mode of binding between
UDP-N-acetylenolpyruvoyl glucosamine reductase and PQAA adducts. All the pyranoquinolinyl/
furoquinolinyl/tetrahydro-cyclopentaquinolinyl acrylic acid (PQAA/FQAA/CPQAA) diastereomers
were thoroughly characterized by NMR, FT-IR, mass spectral, and CHN analysis.
Publisher
Bentham Science Publishers Ltd.