Synthesis of quinoline based [1,2,4]-dithiazolidines through sulfur-sulfur bond formation and their evaluation as anti-inflammatory and antibacterial agents

GRAPHICAL ABSTRACT

Abstract

A series of [1,2,4]-dithiazolidines carrying the quinoline moiety has been synthesized. 2-Chloroquinolin-3-carbaldehyde reacted with various 4-arylthiosemicarbazides to form the corresponding 1-[(2-chloroquinolin-3-yl)methylene]-4-arylthiosemicarbazides. The synthesis of 3,5-(diarylimino)-4[(2-chloroquinolin-3-yl)methyleneamino]-[1,2,4]-dithiazolidines was achieved by the interaction of 1-[(2-chloroquinolin-3-yl)methylene]-4-arylthiosemicarbazides with N-aryl-S-chloroisothiocarbamoyl chlorides through S–S and C–N bond formations. The structures of newly synthesized compounds were confirmed on the basis of IR, ¹H & ¹³C NMR and Mass spectral data. The title compounds were screened for their anti-inflammatory and antibacterial activities.

Keywords:

• [1,2,4]-Dithiazolidine
• 2-Chloroquinolin-3-carbaldehyde; 4-arylthiosemicarbazides
• N-aryl-S-chloroisothiocarbamoyl chloride
• antibacterial activity
• anti-inflammatory activity

Acknowledgments

The authors are thankful to Prof. H.D. Juneja, Head, Post-Graduate Department of Chemistry, RTM Nagpur University, Nagpur, for providing laboratory facilities. They are also thankful to SAIF Chandigarh for spectral analysis and Biogenics, Hubli for biological activity.

Funding

Financial support in the form of SRF to SAC from CSIR, Delhi is gratefully acknowledged.