Synthesis and Anticonvulsant Activity of Some Alkyl Esters of 6-Chloro-2-sulfamoylbenzoic Acid

Anticonvulsants IV: Vinylogs, Alkyl Esters of 2-Sulfamoylcinnamic Acid and Related Compounds

“…Hamor noted previously that secondary alcohol esters of orthosulfamoylbenzoic acid were more active than the esters of primary alcohols (2). In this study, the s-butyl ester (VII, R = s-butyl) was found to possess a slight antielectroshock activity in mice while the other esters did not have any activity.…”

“…In this study, the s-butyl ester (VII, R = s-butyl) was found to possess a slight antielectroshock activity in mice while the other esters did not have any activity. Hamor also observed that the compounds possessing antielectroshock activity had the sulfamoyl and the ester groups sterically crowding each other, especially in the case of the secondary alcohol esters (2). The sulfamoyl and the ester group in IV are not as sterically crowded as they are in I.…”

“…recently reported that the alkyl esters of ortho-sulfamoylbenzoic acid (I), 4-amino-2-sulfamoylbenzoic acid (II), and 6-chloro-2-sulfamoylbenzoic acid (111) were capable of preventing convulsions induced by strychnine or maximal electroshock in mice (1)(2)(3). Loev and Korrnendy also reported on the effectiveness of some 4-amino-2-sulfamoylbenzoates (4,5).…”

Anticonvulsants III

“…Chromatog., 3, 253(1965 It has been proposed that the activity of these sulfamoylbenzoates is related to their resistance to hydrolysis (5). T o support this concept, data correlating anticonvulsant potency with increased chain branching of the alkyl portion of the ester were presented (5). Apart from the steric factors noted, a relationship also appears to exist between the anticonvuisant activity of these esters and the electronic effects of substituents attached to the benzene ring.…”

“…Chromatog., 3, 253(1965 It has been proposed that the activity of these sulfamoylbenzoates is related to their resistance to hydrolysis (5). T o support this concept, data correlating anticonvulsant potency with increased chain branching of the alkyl portion of the ester were presented (5).…”