Synthesis and Anticonvulsant Activity of 1-Substituted-7-Benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Starting from 6-hydroxy-3,4-dihydro-1H-quinoline-2-one, a series of 1-substituted-7-benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolines was synthesized and their structures were characterized using IR, 1H-NMR, MS, and elemental analysis techniques. Anticonvulsant activity was evaluated in the max...

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Bibliographic Details
Published in:Biological & Pharmaceutical Bulletin 2005, Vol.28(7), pp.1216-1220
Main Authors: Cui, Li-Jing, Xie, Zhi-Feng, Piao, Hu-Ri, Li, Gao, Chai, Kyu-Yun, Quan, Zhe-Shan
Format: Article
Language:English
Subjects:
[1,2,4]triazolo[4,3-a]quinoline
Animals
anticonvulsant
Anticonvulsants - chemical synthesis
Anticonvulsants - chemistry
Anticonvulsants - pharmacology
Magnetic Resonance Spectroscopy
Mass Spectrometry
maximal electroshock test
Mice
Mice, Inbred C57BL
neurotoxicity
pentylenetetrazole
Quinolones - chemical synthesis
Quinolones - chemistry
Quinolones - pharmacology
Spectrophotometry, Infrared
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Summary:Starting from 6-hydroxy-3,4-dihydro-1H-quinoline-2-one, a series of 1-substituted-7-benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolines was synthesized and their structures were characterized using IR, 1H-NMR, MS, and elemental analysis techniques. Anticonvulsant activity was evaluated in the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scMet) test, and rotarod neurotoxicity test. The most active compound was 7-benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline 4a. Its ED50 in the MES and scMet tests was 17.3 and 24 mg·kg−1, respectively. The safest compound was 4g, 1-phenyl-7-benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline, with TD50 and protective index (PI) (PI=TD50/ED50) values of greater than 300 mg·kg−1 and 13, respectively. The PI value of compound 4g was better than that of most marketed drugs. Structure–activity relationships are also described in this paper.
ISSN:0918-6158
1347-5215
DOI:10.1248/bpb.28.1216