Structural modifications of the primary amino group of anticonvulsant aryl semicarbazones.
A number of aryl semicarbazones had been shown previously to possess significant anticonvulsant properties. The principal objective of the present investigation was to determine the importance of the primary amino group in this series of compounds by replacing it with other substituents. The results indicate that the amino group was not essential for anticonvulsant activity. However its replacement by an aryl ring generally abolished activity while a terminal phenylamino function was better tolerated. Thus both the size of the group and its hydrogen bonding capabilities appear to influence bioactivity. Alteration of the oxygen atom of the semicarbazones by isosteres did not enhance anticonvulsant properties.
Dimmock
J R
JR
College of Pharmacy and Nutrition, University of Saskatchewan, Saskatoon, Canada.
Puthucode
R N
RN
Lo
M S
MS
Quail
J W
JW
Yang
J
J
Stables
J P
JP
D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004597:Electroshock; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D009498:Neurotoxins / Q000037:antagonists & inhibitors / Q000633:toxicity; D010433:Pentylenetetrazole; D051381:Rats; D012640:Seizures / Q000139:chemically induced / Q000503:physiopathology / Q000517:prevention & control; D012664:Semicarbazones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000927:Anticonvulsants; D009498:Neurotoxins; D012664:Semicarbazones; D010433:Pentylenetetrazole