Cyclic N‐2‐Chloroethyl‐sulfamide Compounds with a Phosphonate Moiety: Synthesis, Characterization, X‐Ray Crystallographic Study and Antimicrobial Evaluation

Abstract

An efficient access to a novel series of organophosphorus compounds with a cyclosulfamide moiety is described. Starting from α-hydroxyphosphonates, the 2-chloroethyl-(1, 2, 5-thiadiazoline-2-carbonyloxy-1-dioxide) phosphonates compounds were prepared in three steps including an Abramov reaction, carbamoylation-sulfamoylation with chlorosulfonyl isocyanate and an intramolecular cyclisation. The spectroscopic methods( 1 H NMR, 13 C NMR, 31 P NMR, MS and IR) were used to determine the structural characteristics of the synthesized compounds and X-ray crystallographic data were provided for compound 3c. Some selected compounds were screened in vitro for their antimicrobial activity against a panel of microorganisms, resulting in a good antibacterial activity compared to standard drugs.

In vitro antitumor activity, molecular dynamics simulation, DFT study, ADME prediction, and Eg5 binding of enastron analogues

“…On the other hand, benzothiadiazinone dioxides (also called cyclosulfamides) are important heterocyclic-based compounds bearing the sulfamide moiety that is recognized as a remarkable pharmacophore with a high number of applications in the fields of medicinal chemistry and drug development. 16 Different pharmacological activities of cyclic sulfamides were reported in the literature comprising antibacterial, 17 antiviral, 18 anti-inflammatory, 19 and anticancer activities. 20 Further, the high capacity of cyclosulfamides in inhibiting many enzymes and target proteins such as phosphodiesterase 7 (PDE7), 21 aspartic proteases, 22 and serine proteases 23 turned interest of scientists to conceive more molecules containing this scaffold.…”

A New family of Sulfamidophosphonates Derivatives: Microwave‐Accelerated Multicomponent Synthesis, Characterization and X‐Ray Crystallographic Study**

“…But surprisingly, in the literature, very few works have been reported on the synthesis of bifunctional compounds containing both sulfamide and phosphonate moieties [52,53] . In this context, our laboratory group research based on the development of novel biomolecules by effective and simplified procedures [54,55] . In 2015, Belhani et al .…”

“…[52,53] In this context, our laboratory group research based on the development of novel biomolecules by effective and simplified procedures. [54,55] In 2015, Belhani et al reported a simple and efficient method for the synthesis of a novel α-sulfamidophosphonates ultrasound activation and solvent-free conditions with excellent yields. [56] Recently, Guerfi et al described novel α-sulfamidophosphonates analogues of fotemustine by an efficient synthesis using ultrasound under solvent free conditions.…”

Experimental synthesis, biological evaluation, theoretical investigations of some novel benzoxazolinone based Schiff under eco-environmental conditions as potential antioxidant agents

“…Generally, catalyst-free and solvent-free processes can be achieved using microwave irradiation. [38,39] In continuation of our field of study on the synthesis and biological evaluation of organo-phosphorus and -sulfur compounds, [40][41][42][43] we describe here a simplified three-component one-pot synthesis of sulfamide-containing bisphosphonates derivatives under microwave irradiation. This method respects remarkable principles of green chemistry; atom economy, design for energy efficiency, safety and environment friendly without using any catalyst or solvent, thus reduce chemical waste and reaction time.…”