Anticonvulsant evaluation of some 3-oxo and 3-thiosemicarbazono analogues of 1-aryl-1-ethylthio-nonanes and related compounds.
A number of 3-oxo and 3-thiosemicarbazono analogues of 1-aryl-1-ethylthio-nonanes and related compounds were synthesized. Solutions of the thiosemicarbazones in deuterochloroform were shown by PMR spectroscopy to exist principally in the anti configuration at equilibria except when an ortho-methoxy group was present in the aryl ring. In this case intramolecular hydrogen bonding probably accounts principally for the presence of equal amounts of anti and syn isomers. Evaluation of these compounds for anti-convulsant properties revealed that 1-(2-aminoethylthio)-1-(2-chlorophenyl)nonan-3-one hydrochloride (6a) and sodium 2-(N-acetylamino)-3-[1-(2-chlorophenyl)-3-oxononylthio]propionate (6c) were active and thus they could serve as prototype molecules for future development.
D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002722:Chlorobenzenes / Q000138:chemical synthesis* / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical; D005021:Ethylamines / Q000138:chemical synthesis* / Q000494:pharmacology; D007659:Ketones / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000494:pharmacology
D000927:Anticonvulsants; D002722:Chlorobenzenes; D005021:Ethylamines; D007659:Ketones; D013882:Thiosemicarbazones; C052877:1-(2-aminoethylthio)-1-(2-chlorophenyl)nonan-3-one; C052878:2-(N-acetylamino)-3-(1-(2-chlorophenyl)-3-oxononylthio)propionate