Synthesis of novel 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones as anticonvulsant agents

被引：28
作者：
Piao, Zhong-Tai [1 ,2 ]
Guan, Li-Ping [1 ]
Zhao, Li-Ming [1 ]
Piao, Hu-Ri [1 ]
Quan, Zhe-Shan [1 ,2 ]
机构：
[1] Yanbian Univ, Coll Pharm, Yanji 133000, Jilin Province, Peoples R China
[2] Yanbian Univ, Key Lab Organism Funct Factors Changbai Mt, Minist Educ, Yanji 133000, Jilin Province, Peoples R China
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2008年 / 43卷 / 06期
基金：
中国国家自然科学基金;
关键词：
1,4-benzoxazin-3(4H)-one; anticonvulsant; MES; sc-PTZ; isoniazid; strychnine;
D O I：
10.1016/j.ejmech.2007.08.006
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones were synthesized using 2-amino-5-nitrophenol as a starting material. Their anticonvulsant activities were evaluated by the maximal electroshock test (MES test) and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox.). The MES test showed that 7-(4-fluorobenzylamino)-2H-1,4-benzoxazin-3(4H)-one 4b was the most potent with ED50 Value of 31.7 mg/kg and protective index (PI = TD50/ED50) value of 7.2. To explain the possible mechanism of anticonvulsant activity, the compound 4b was tested in sc-PTZ test, isoniazid test and strychnine test. (c) 2007 Published by Elsevier Masson SAS.
引用
收藏
页码：1216 / 1221
页数：6
相关论文
共 50 条
  • [41] Novel spiro[indene-1,2′-quinazolin]-4′(3′H)-one derivatives as potent anticonvulsant agents: One-pot synthesis, in vivo biological evaluation, and molecular docking studies
    Mohammadi, Ali Asghar
    Taheri, Salman
    Shisheboran, Sanaz
    Ahdenov, Reza
    Mohammadi-Khanaposhtani, Maryam
    Darjani, Pedram Salehi
    Masihi, Patrick Honarchian
    Shakiba, Aidin
    Larijani, Bagher
    Mahdavi, Mohammad
    Ahangar, Nematollah
    JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY, 2023, 37 (01)
  • [42] Synthesis and Evaluation of the Anticonvulsant Activities of 4-(2-(Alkylthio)benzo[d]oxazol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ones
    Song, Ming-Xia
    Wang, Zhen-Yuan
    He, Shi-Hui
    Yu, Sheng-Wang
    Chen, Shi-Long
    Guo, Dong-Fu
    Zhao, Wen-Hao
    Deng, Xian-Qing
    MOLECULES, 2018, 23 (04):
  • [43] Synthesis, resolution and anticonvulsant activity of chiral N-1′-ethyl,N-3′-(1-phenylethyl)-(R,S)-2′H,3H,5′H-spiro-(2-benzofuran-1,4′-imidazolidine)-2′,3,5′- trione diastereomers
    Sadarangani, Ishwar R.
    Bhatia, Souful
    Amarante, Daniel
    Lengyel, Istvan
    Stephani, Ralph A.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (07) : 2507 - 2509
  • [44] Synthesis and anticonvulsant activity study of 7-substituted phenoxyl-4,5-dihydro[1,2,4]triazolo[4,3-a]quinolines and quinoline-1(2H)-ones
    Jin, Yun-Zhe
    Guan, Li-Ping
    Zhao, Li-Ming
    Piao, Hu-Pi
    Quan, Zhe-Shan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (12) : 1567 - 1572
  • [45] Synthesis and anticonvulsant activity evaluation of 7-alkoxy-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-1-ones in various murine experimental seizure models
    Cao, Xu
    Wang, Shi-Ben
    Deng, Xian-Qing
    Liu, Da-Chuan
    Quan, Zhe-Shan
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (04) : 1829 - 1838
  • [46] Anticonvulsant and sedative-hypnotic activity of some novel 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2-styrylquinazoline-4(3H)-ones
    Sushil K. Kashaw
    Vivek Gupta
    Varsha Kashaw
    P. Mishra
    J. P. Stables
    N. K. Jain
    Medicinal Chemistry Research, 2010, 19 : 250 - 261
  • [47] Anticonvulsant and sedative-hypnotic activity of some novel 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2-styrylquinazoline-4(3H)-ones
    Kashaw, Sushil K.
    Gupta, Vivek
    Kashaw, Varsha
    Mishra, P.
    Stables, J. P.
    Jain, N. K.
    MEDICINAL CHEMISTRY RESEARCH, 2010, 19 (03) : 250 - 261
  • [48] Synthesis and anticonvulsant activity evaluation of 7-alkoxy-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-1-ones in various murine experimental seizure models
    Xu Cao
    Shi-Ben Wang
    Xian-Qing Deng
    Da-Chuan Liu
    Zhe-Shan Quan
    Medicinal Chemistry Research, 2014, 23 : 1829 - 1838
  • [49] CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones
    Jatav, Varsha
    Mishra, Pradeep
    Kashaw, Sushil
    Stables, J. P.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (09) : 1945 - 1954
  • [50] Synthesis and Anticonvulsant Activity Evaluation of 4-Aryl-3,4-dihydropyrimidin-2(1H)-(thi)one
    Tang, Wen-Li
    Bi, Fu-Long
    Wei, Cheng-Xi
    LATIN AMERICAN JOURNAL OF PHARMACY, 2017, 36 (07): : 1308 - 1315
12345