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. 3,4Dichloro-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-1phenyl-4-pyrrolidin-1-yl-1H-pyrrole-2,5-dione (2). 4-(3-Chloro-2,5-dioxo-4-pyrrolidin-1-yl-2,5dihydro-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-4pyrrolidin-1-yl-2,5-dihydro-1H-pyrrol-1-yl)benzenesulfonohydrazide (4), which was characterized through condensation with aldehydes to yield the imidosulfonylhydrazones (5-12).
Highlights
The synthesis of sulfonylhydrazones is of great interest since these compounds have shown antiinflammatory, analgesic[1,2,3], anti-pyretic[4], and antibacterial activities[5]
Studies carried out by Barreiro et al have shown that sulfonylhydrazone derivatives of safrole have potent analgesic action, exceeding and/or equalling the potency observed under the same conditions for either dypirone or indomethacin[7]
This paper describes the synthesis of chloromaleimidobenzenesulfonylhydrazones, in a search for antibactericidal and/or antinociceptive lead compounds
Summary
The synthesis of sulfonylhydrazones is of great interest since these compounds have shown antiinflammatory, analgesic[1,2,3], anti-pyretic[4], and antibacterial activities[5]. Was obtained from the reaction of compound (1) (1 mol) and pyrrolidine (2 mol) in dichloromethane at room temperature[9].
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