2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

Sangeetha Karanth,Badiadka Narayana,Sharath Kodandoor,Balladka Sarojini

doi:10.3390/m1009

Abstract

Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as the catalyst. The structure of the title compound is determined by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectral data. In order to determine the molecular interactions with the bacterial enzyme, the title compound is further docked into the active site of the MurB protein of Staphylococcus aureus (PDB ID: 1HSK). The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. The compound is also evaluated for its antioxidant property by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging assay.

Highlights

The chemical modification of compounds containing 4-thiazolidinone moiety leads to their wide appositeness as efficacious pharmacological agents, paving the way for their discernible antimicrobial [5,6], antimalarial [7], anti-HIV [8], antioxidant [9], anticancer [10,11,12,13], antiarrhythmic [14] and anti-inflammatory [15,16]
The compound 1 was in turn in a mixture of toluene and dimethyl formamide (DMF) (25:1)
The compound 1 was in turn synthesized through the hydrazone synthesized through the hydrazone condensation between 4-hydroxy-3,5-dimethoxybenzaldehyde condensation between 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in ethanol, using a and thiosemicarbazide in ethanol, using a few drops of acetic acid as the catalyst [17]

Summary

Introduction

The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. Thiosemicarbazones have been reported for their wide spectrum of antibacterial [1], anticancer [2,3], anti-inflammatory and antioxidant activities [4]. The chemical modification of compounds containing 4-thiazolidinone moiety leads to their wide appositeness as efficacious pharmacological agents, paving the way for their discernible antimicrobial [5,6], antimalarial [7], anti-HIV [8], antioxidant [9], anticancer [10,11,12,13], antiarrhythmic [14] and anti-inflammatory [15,16]. Development of molecules with the property of targeting proteins concerned with initial stages of peptidoglycan biosynthesis can assure a better bactericidal effect than most of the clinically

Methods

Results

Discussion

Conclusion