N,N’-Substituted 1,2,5 Thiadiazolidine 1,1-Dioxides: Synthesis, Selected Chemical and Spectral Proprieties and Antimicrobial Evaluation †

A Bendjeddou,R Djeribi,Z Regainia,N Aouf

doi:10.3390/10111387

Abstract

The sulfamide functional group is increasingly relevant in both medicinal and bioorganic chemistry. We report here practical access to a series of N2,N5-substituted five-membered cyclosulfamides. The five-membered heterocyclic motif was prepared starting from proteogenic amino acids and chlorosulfonyl isocyanate via the Mitsunobu reaction. Selected chemical and spectral proprieties and the antimicrobial evaluation of these compounds are detailed.

Highlights

The synthesis and reactivity of heterocyclic compounds containing sulfonyl moieties have attracted much interest in recent years because of the interesting chemical and biological proprieties associated with their structural similarities with biomolecules containing carbonyl groups
In previous publications [13,14,15], we have described a convenient access to a series of five and n-membered cyclic sulfamides B and N,N’-disubstituted orthogonally protected ones A (Figure 1), starting from natural amino acids, chloroethylamine and chlorosulfonylisocynanate (CSI) followed by 5-exo-tet closure with base
In continuation of our efforts to design and synthesize new cyclic sulfamides, we have extended our studies to a series of new heterocyclic constrained peptides containing sulfamide groups C and D (Figure 1)

Summary

Introduction

The synthesis and reactivity of heterocyclic compounds containing sulfonyl moieties have attracted much interest in recent years because of the interesting chemical and biological proprieties associated with their structural similarities with biomolecules containing carbonyl groups.

Results

Conclusion