• Title/Summary/Keyword: 2(1H)-Quinolinone

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Synthesis of 6-Alkyloxyl-3,4-dihydro-2(1H)-quinoliones and Their Anticonvulsant Activities

  • Quan, Zhe Shan;Wang, Jun-Min;Rho, Jung-Rae;Kwak, Kyung-Chell;Kang, Hee-Cheol;Jun, Chang-Soo;Chai, Kyu-Yun
    • Bulletin of the Korean Chemical Society
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    • v.26 no.11
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    • pp.1757-1760
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    • 2005
  • 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 $ED_{50}$ of 24.0 mg/kg and 21.2 mg/kg, respectively, albeit its $TD_{50}$ (67.6 mg/kg) revealed the high neurotoxicity. 6-Benzyloxy-3,4-dihydro-2(1H)-quinolinone (5f) was less effective against MES induced seizure with $ED_{50}$ 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.

Antifungal Activity of the Extracts of Zanthoxylum Schinifolium Sieb. et Zucc. against Dermatophytes (산초나무 추출물의 피부사상균에 대한 항균활성과 그 성분)

  • Min, Kyeong-Heui
    • Journal of the Korean Wood Science and Technology
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    • v.26 no.4
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    • pp.78-85
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    • 1998
  • The antifungal activity of methanol extracts against dermatophytes was the highest at root-bark methanol extract, and the highest inhibitory effect was revealed in petroleum ether fraction of root-bark methanol extract. Compound I and compound II with significant antifungal activity were isolated from the fractions by silica gel column chromatography. As a result of the instrumental analyses, compound I and compound II were already known alkaloids. Compound I was identified as 4-methoxyfuro[2,3-6]quinoline (dictamnine ; $C_{12}H_9NO_2$) and compound II was identified as 4-methoxy-lmethyl-2(1H)-quinolinone ($C_{11}H_{11}NO_2$). The MIC of compound I against T. mentagrophytes and T. rubrum was $40{\mu}g/m\ell$ and the MIC of compound II against the same fungi was $800{\mu}g/m\ell$.

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Therapeutic Effect of Rebamipide on Ammonia-induced Gastric Mucosal Hemorrhagic Lesion in Rats

  • Huh, Keun;Kwon, Tae-Hyub;Kim, Soo-Kyun;Kim, Jin-Sook;Shin, Uk-Seob
    • Archives of Pharmacal Research
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    • v.21 no.1
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    • pp.1-5
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    • 1998
  • Rebamipide, 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinone-4-yl]-propionic acid, a novel antipeptic ulcer agent, has been reported to prevent various acute experimental gastric mucosal lesions and to accelerate the healing of chronic ulcers. Therapeutic effect of rebamipide was investigated with regard to the inhibitory effect on xanthine oxidase activity and type conversion of the enzyme which play a profound role in oxygen radicals generation system. Intraperitoneal administration of rebamipide at 60 mg/kg body weight reduced the xanthine oxidase activity, lipid peroxide content in ammonia induced hemorrhagic lesion. These results suggest that the therapeutic effect of rebamipide on gastric mucosal lesion may be in part due to the inhibitory activity of xanthine oxidase and type conversion rate of the enzyme.

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Isolation and Identification of 3 Low-molecular Compounds from Pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) Fruit Peel (추황배(Pyrus pyrifolia Nakai cv. Chuhwangbae) 과피로부터 3종의 저분자 화합물의 단리·동정)

  • Lee, Yu Geon;Cho, Jeong-Yong;Kim, Chan-Mi;Jeong, Hang-Yeon;Lee, DongI;Kim, Soo Ro;Lee, Sang-Hyen;Kim, Wol-Soo;Park, Keun-Hyung;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.45 no.2
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    • pp.174-179
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    • 2013
  • Three low-molecular compounds were isolated from methanol extracts of pear (Pyrus pyrifolia N. cv. Chuhwangbae) fruit peels using solvent fractionation, various types of column chromatogrphy (Diaion HP-20, Sephadex LH-20, and silica gel), and high performance liquid chromatography with an assay guided by 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity. The isolated compounds were identified as 2-carboxyl-4(1H)-quinolinone (kynurenic acid, 1) from butanol fraction, cis-p-coumaric acid (2) from ethyl acetate-acidic fraction, and vanillin (3) from the ethyl acetate-phenolic fraction, respectively. These isolated compounds were confirmed on the basis of the spectroscopic data of electrospray ionization mass spectrometry and nuclear magnetic resonance. This is the first time that compounds 1-3 were isolated and identified in pear.