Synthesis and anticonvulsant activity of 5-phenyl-[1,2,4]-triazolo[4,3-a]quinolines.
A series of novel 5-phenyl-[1,2,4]-triazolo[4,3-a]quinoline derivatives was synthesized by the cyclization of 2-chloro-4-phenyl-1,2-dihydronaphthalene with formohydrazide. The starting material 2-chloro-4-phenyl-1,2-dihydronaphthalene was synthesized from ethyl-3-oxo-3-phenylpropanoate and substituted aniline. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The maximal electroshock test showed that 7-hexyloxy-5-phenyl-[1,2,4]-triazolo[4,3-a]quinoline 4f was found to be the most potent compound with an ED(50) value of 6.5 mg/kg and a protective index (PI = ED(50) / TD(50)) value of 35.1, which was much higher than the PI of the reference drug phenytoin.
Guan
Li-Ping
LP
Key Laboratory of Organism Functional Factors of Changbai Mountain (Yanbian University), Ministry of Education, Yanji, Jilin, PR China.
Jin
Qing-Hao
QH
Wang
Shou-Feng
SF
Li
Fu-Nan
FN
Quan
Zhe-Shan
ZS
D000814:Aniline Compounds / Q000737:chemistry; D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D004597:Electroshock / Q000009:adverse effects; D051379:Mice; D009281:Naphthalenes / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000627:therapeutic use; D013329:Structure-Activity Relationship
D000814:Aniline Compounds; D000927:Anticonvulsants; D009281:Naphthalenes; D015363:Quinolones; C031721:naphthalene; C023650:aniline