Pyridine and Benzoisothiazole Decorated Vanillin Chalcones: Synthesis, Antimicrobial, Antioxidant, Molecular Docking Study and ADMET Properties

Pintu Pathare; Sunil Tekale; Rafique Shaikh; Manoj Damale; Jaiprakash Sangshetti; Dhanaji Rajani; Rajendra Pawar

doi:10.2174/1570179417666200407130122

Pyridine and Benzoisothiazole Decorated Vanillin Chalcones: Synthesis, Antimicrobial, Antioxidant, Molecular Docking Study and ADMET Properties

Curr Org Synth. 2020;17(5):367-381. doi: 10.2174/1570179417666200407130122.

Authors

Pintu Pathare¹, Sunil Tekale¹, Rafique Shaikh², Manoj Damale³, Jaiprakash Sangshetti⁴, Dhanaji Rajani⁵, Rajendra Pawar¹

Affiliations

¹ Department of Chemistry, Deogiri College, Station Road, Aurangabad (MS) 431005, India.
² Department of Botany, Poona College of Arts, Commerce and Science, Pune (MS) 411 001, India.
³ Department of Pharmaceutical Chemistry, Shrinath College of Pharmacy, Aurangabad (MS) 431136, India.
⁴ Y. B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Aurangabad (MS) 431 001, India.
⁵ Microcare Laboratory and Tubercular Research Centre, Surat (Gujrat) 395 003, India.

PMID: 32264812
DOI: 10.2174/1570179417666200407130122

Abstract

Background: The search for new antimicrobial drugs is a never-ending task due to microbial resistance to the existing drugs. Antioxidants are essential to prevent free radical reactions which lead to chronic diseases to humankind.

Objective: The present studies were aimed at synthesis, characterization, antimicrobial and antioxidant activities of pyridine and benzoisothiazole decorated chalcones.

Materials and methods: FTIR spectra were recorded using KBr pellets on Shimadzu FT-IR spectrophotometer. 1H and 13C NMR spectra were recorded on Bruker 400 MHz spectrometer. Antimicrobial activity of the synthesized chalcones was found to be good against different bacterial and fungal strains. Antioxidant activity was studied in terms of 2,2-diphenyl-1-picrylhydrazyl, hydroxyI and superoxide radical scavenging activities. Molecular docking was studied using Discovery Studio Visualizer Software, version 16 whereas Autodock Vina program was used to predict the toxicity profile of the compounds using FAFDrugs2 predictor.

Results and discussion: The compounds 5c, 5d & 6c showed good antioxidant activities. The insilico molecular docking study supports the experimental results and demonstrated that the chalcones 5d, 6a and 7a are the most active among the synthesized derivatives.

Conclusion: Prediction of pharmacokinetic parameters and molecular docking studies suggest that the synthesized chalcones have good pharmacokinetic properties to act as lead molecules in the drug discovery process.

Keywords: ADMET; Benzoisothiazole; antimicrobial; antioxidant; chalcones; molecular docking; pyridine.