Paper
Anticonvulsants. 3. Alkyl esters of 4-bromo-2-sulfamoylbenzoic acid and 4-chloro-2-sulfamoylbenzoic acid.
Published 1967 · G. H. Hamor, B. L. Reavlin
Journal of pharmaceutical sciences
14
Citations
1
Influential Citations
Abstract
In addition to steric factors, electronic effects may also be important in the anti-convulsant activity of alkyl o -sulfamoylbenzoates and related compounds. To further explore the relationship between electronic properties and antielectroshock activity, three esters of 4-bromo-2-sulfamoylbenzoic acid and four esters of 4-chloro-2-sulfamoylbenzoic acid were prepared by the alcohlysis reaction of passing hydrogen chloride into a refluxing solution of 6-bromo- or 6-chlorosaccharin in the appropriate alcohol. The following alkyl 4-bromo- and 4-chloro-2-sulfam-oylbenzoates were thus obtained: methyl; ethyl; i -propyl; and sec -butyl. In these compounds the bromine or chlorine atom is in the 4-position para to the alkoxycarbonyl group; thus, they do not possess the steric interactions between the large halogen atom and the ester moiety, which are believed to be necessary in the anticonvulsant activity of the related, potent ortbo -substituted alkyl 6-chloro-2-sulfamoylbenzoates. Preliminary pharmacological results indicate that isopropyl 4-bromo-2-sulfamoylbenzoate lacks antielectroshock effects in mice.
Alkyl esters of 4-bromo-2-sulfamoylbenzoic acid and 4-chloro-2-sulfamoylbenzoic acid lack antielectroshock effects in mice, suggesting electronic effects may play a role in their anticonvulsant activity.
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