Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives.

Ramesh Ramesh,Hong Hong,Reddy Reddy,Rao Rao

doi:10.3390/molecules24173038

Ramesh Ramesh, Hong Hong + Show 2 more

Open Access

https://doi.org/10.3390/molecules24173038

Copy DOI

Abstract

A series of 2-hydroxy-3-chrysino dithiocarbamate derivatives (3a–k) were designed, synthesized, and characterized for their structure determination by 1H NMR, 13C NMR, and HRMS (ESI) spectral data. They were screened for their in vitro biological activities against a panel of selected bacterial and fungal strains. These antimicrobial studies indicate that some of the analogues manifested significant activity compared to standard drugs. Among the synthetic analogues (3a–k), compounds 3d, 3f, and 3j exhibited very good antibacterial activity and compounds 3d, 3f, and 3h showed very good antifungal activity compared to the standard drugs penicillin and itrazole, respectively. The compounds 3e, 3g, and 3h showed moderate antibacterial activity and the compounds 3j and 3k showed moderate antifungal activity. Molecular docking studies were performed and the experimental antimicrobial screening results were also correlated with the binding energy values obtained by molecular docking. The synthesized chrysin analogues (3a–k) have obeyed Lipinski’s “rule of five” and have drug-likeness.

Highlights

In the recent past, many pharmaceutical products have been designed and developed using plant based lead compounds like polyphenols [1]
Our aim is to enhance the biological activity of chrysin by linking it to 22-hydroxy dithiocarbamates at
Epoxy-methyl group wasgroup was was linked to chrysin at its position by reacting with epichlorohydrin in presence of 3 in linkedtotochrysin chrysin position by reacting with epichlorohydrin in presence linked at at itsits position by reacting with epichlorohydrin in presence of K2CO3 of in DMF

Summary

Introduction

Many pharmaceutical products have been designed and developed using plant based lead compounds like polyphenols [1]. Flavonoids exhibit a wide variety of biological activities like antibacterial, anti-inflammatory, anti-diabetic, anti-allergic, antiviral, vasodilatory, and anticancer activities [7,8,9,10,11,12,13,14,15,16,17] and have potential to be developed or modified as effective drug candidates. Chrysin (5,7-dihydroxy flavone) is an important biologically active compound. Chrysin is reported to exhibit various biological activities, which includes antibacterial [31], anti-inflammatory [32] anti-allergic [33], antioxidant [34], and anticancer [35] activities. Several attempts have been made to synthesize the structural derivatives

Objectives

Methods

Results

Conclusion