Synthesis and characterization of chloromaleimidobenzenesulfonylhydrazones

Abstract

This paper describes the synthesis of a new series of imidosulfonylhydrazones in a search for antibactericidal and/or antinociceptive lead compounds.Cyclic imides comprise an important family of organic compounds with therapeutic potential, including the sulfonylhydrazones. 3,4-Dichloro-1-phenyl-1H-pyrrole-2,5-dione (1) was obtained from the reaction between aniline and dichloromaleic anhydride in acetic acid. Reaction of (1) with pyrrolidine gave 3-chloro-1-phenyl-4-pyrrolidin-1-yl-1H-pyrrole-2,5-dione (2). 4-(3-Chloro-2,5-dioxo-4-pyrrolidin-1-yl-2,5-dihydro-1H-pyrrol-1-yl)benzenesulfonyl chloride (3) was obtained from the chlorosulfonation of compound (2). The reaction of (3) with hydrazine hydrate produced 4-(3-chloro-2,5-dioxo-4-pyrrolidin-1-yl-2,5-dihydro-1H-pyrrol-1-yl)benzenesulfonohydrazide (4), which was characterized through condensation with aldehydes to yield the imidosulfonylhydrazones (5-12).

Investigation of Photochemical Reactions of some Metal Carbonyls with N´-(2-Hydroxy-6- Methylbenzylidene)Methanesulfonohydrazide and 5-Methyl- 2-Hydroxyacetophenonemethanesulfonylhydrazone

“…They are less toxic as compared to other drugs and are scalable. 8,9 In chemical synthesis, photochemical reactions are usually cleaner and more efficient than other types of reactions because the key reagent is light of particular energy. In fine chemical synhhesis and pharmaceutical productions, photochemical reaction steps offer shorter routes for many synthetic schemes, e.g.…”

Synthesis and Evaluation of Anti-Lipase Potential and Molecular Docking of N’-(2-Hydroxy-5-nitrobenzylidene) naphthalene-2-sulfonohydrazide

“…It is represented in drugs such as methane sulfonyl hydrazide which shows antibacterial effect (Ozdemir et al, 2015). Sulfonyl hydrazide behaves also as DNA binder agent and has antitumor actions against several tumor types (Silva et al, 2006). Sulfonyl hydrazine's derivatives also behave as cancer chemotherapeutic agents such as: 1, 2-bis (methylsulfonyl) -1-2 (methylamino) carbonyl-hydrazine, which exhibits broad anticancer activities (Zhao et al, 2015).…”

Benzyl and Sulfonyl Derivatives of N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide (T2288): Biological Screening and Fingerprint applications

“…Many scientific repor ts reveals that sulfonyl group when linked to piperazine derivatives possess wide pharmacological activities like anti-inflammatory 18 , antidiabetic 19 , anticancer [20][21][22][23] , antibacterial [24][25] , antiprotozoal 26 , antifungal [27][28] , nonpeptidic vasopressin receptor antagonists 29 and translation initiation inhibitors [30][31] . In addition, many acetamide derivatives have been reported to exhibit various biological activities such as anthelmintic, anticonvulsant, antioxidant, anti-inflammatory, anti-ar thritic, anticancer, anti-bacterial and antifungal [32][33][34][35][36] .…”