The facile and efficient ultrasound-assisted synthesis, molecular docking and antimicrobial evaluation of 1, 3-dithiane derivatives
Author (s): Mohammad Arif Pasha1, Sumanta Mondal1, Naresh Panigrahi1*
A new, simple and efficient method for the synthesis of novel 1, 3- dithiane derivatives under ultrasonic conditions via a one-pot threecomponent reaction of activated methylene group malononitrile with carbon disulfide in the presence of arylidene malononitriles was reported. The effects of LiOH.H2O as a base under ultrasonic conditions at different concentrations have been investigated and the reaction provided products with good yields at 40-50.C temperature. Explorations of synthesized 1,3-dithiane substituted (ketene dithioacetals) compounds for the antimicrobial study were found to be effective towards S. aureus (ACPDM-5 and ACPDM- 13) with a zone of inhibition at 26mm and 22mm, which is compared to that of standard ciprofloxacin (26mm). This made our study to explore the inhibition mechanism with the help of molecular docking studies with possible binding energies (-6.4 to – 8.9 kJ/mol) by pyrx 0.8 software to represent a good prediction of interactions between the ligand and protein (2XCT). Based on the in-vitro and in-silico studies a series of ketene dithioacetals compounds may be helpful for further studying SAR, ADMET and designing antimicrobials that are more potent.
LiOH.H2O (lithium hydroxide monohydrate); 1,3- dithiane derivatives(ketene dithioacetals); Ultrasonication; onepot three-component reaction; antimicrobial activities; molecular docking.