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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 26, Number 11
BKCSDE 26(11)
November 20, 2005 

Synthesis of 6-Alkyloxyl-3,4-dihydro-2(1H)-quinoliones and Their Anticonvulsant Activities
Zhe-Shan Quan, Jun-Min Wang, Jung-Rae Rho, Kyung-Chell Kwak, Hee-Cheol Kang, Chang-Soo Jun, Kyu-Yun Chai*
[1,2,4]Triazolo[4,3-a]quinoline, Anticonvulsant, Maximal electroshock, Pentylenetetrazole, Neurotoxicity
A series of 6-alkyloxyl-3,4-dihydro-2(1H)-quinoliones (5a-5n) were synthesized through nitration, reduction, diazotization, hydrolysis and alkylation from 3,4-dihydro-2(1H)-quinolione. Their structures were characterized by IR, 1H-NMR and MS. The anticonvulsant activity was evaluated by the Maximal electroshock test (MES) and the subcutaneous pentylenetetrazole (Metrazole) test (sc-Met). The neurotoxicity was measured by the Rotarod test (Tox). The result showed that 6-hexyloxy-3,4-dihydro-2 (1H)-quinolinone (5c) was potent in anti-MES and anti-scMet test with ED50 of 24.0 mg/kg and 21.2 mg/kg, respectively, albeit its TD50 (67.6mg/kg) revealed the high neurotoxicity. 6-Benzyloxy-3,4-dihydro-2(1H)-quinolinone (5f) was less effective against MES induced seizure with ED50 of 29.6 mg/kg, but no neurotoxicity was observed even under 300 mg/kg. Its Protective index (PI) was greater than 10 preferable to Phenytoin, Carbamazepin, Phenobarbital and Valproate.
1757 - 1760
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