Synthesis of novel pyrazoline-thiazolidin-4-one hybrids and evaluation their biological activity

Serhii Holota

doi:10.15407/bioorganica2021.01.018

Abstract

In the present work, the synthesis of pyrazoline-thiazolidin-4-one hybrids and their pharmacological properties are described. The structure of compounds is characterized using 1H, 13C NMR, and LC-MS spectra. The antioxidant (DPPH assay), antimicrobial (Gram-positive bacterium Lactobacillus plantarum, Gram-negative bacterium Escherichia coli, and yeasts Candida albicans, MIC determination), redox (cyclic voltammetry) as well as herbicidal activity (against grass species Agrostis stolonifera) of compounds have been studied. All derivatives have demonstrated radical scavenging activity with IC50 values in the range from 4.67-7.12 mM in the DPPH test. The tested compounds presented very low antimicrobial and herbicidal activity and no redox peaks were observed in the cyclic voltammetry studies.

Highlights

The last decade has witnessed a growing interest in the development of redox modulating agents as effective tool in therapy oxidative-stress associated processes: cancers, diabetes, inflammatory diseases, neurological disorders, and others [1,2,3,4]
The application of the mentioned scaffolds is an attractive direction for the development of selective modulators of Nrf2 and NF-kB transcription factors, that play a key role in the regulation of cellular responses to oxidative-stress factors and are potential drug targets [9,10,11]
In our early-described researches some types thiazolidin4-one hybrids linked through “enamine” linker at C-5 has been synthesized and several compounds been have been identified with a high level of antibacterial and antifungal [12,13,14], anticancer and trypanocidal [15], and antiinflammatory activity [16] (Figure 1)

Summary

Introduction

The last decade has witnessed a growing interest in the development of redox modulating agents as effective tool in therapy oxidative-stress associated processes: cancers, diabetes, inflammatory diseases, neurological disorders, and others [1,2,3,4]. In this context, the structure modified thiazolidin-4-one and pyrazoline nucleus are prospective molecular platforms for design antioxidants and redoxmodulating agent design [5,6,7,8]. Taking into account the above reasons, the main goal of the present work was the design and synthesis of novel “enamine”-bearing pyrazoline-thiazolidin-4-one hybrid molecules and further evaluation of their antioxidant, antimicrobial, herbicidal, and redox activities

Results and Discussion

Findings

Conclusions