methyl 4'-<(4'-chloro-2'-pyridinyl)amino>-6-methyl-2-oxocyclohex-3-en-1-oate | 149221-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 4'-<(4'-chloro-2'-pyridinyl)amino>-6-methyl-2-oxocyclohex-3-en-1-oate
• 英文别名: methyl 4-[(4'-chloro-2'-pyridinyl)amino]-6-methyl-2-oxo-3-cyclohexen-1-carboxylate；methyl 4-[(5-chloro-2-pyridyl)amino]-6-methyl-2-oxo-3-cyclohexene-1-carboxylate；Methyl 4-((5-chloro-2-pyridinyl)amino)-6-methyl-2-oxo-3-cyclohexene-1-carboxylate；methyl 4-[(5-chloropyridin-2-yl)amino]-6-methyl-2-oxocyclohex-3-ene-1-carboxylate
• CAS: 149221-14-7
• 化学式: C₁₄H₁₅ClN₂O₃
• 分子量: 294.738
• InChiKey: BFAOEAQFZQPPRV-UHFFFAOYSA-N

物化性质

• 沸点：
  422.5±45.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-5-氯吡啶 、 甲基6-甲基-2,4-环己二酮羧酸酯 以 苯 为溶剂， 反应 5.0h， 以43%的产率得到methyl 4'-<(4'-chloro-2'-pyridinyl)amino>-6-methyl-2-oxocyclohex-3-en-1-oate
  参考文献：
  名称：

  烯胺酮的合成和抗惊厥活性。2.进一步的结构活性相关性。

  摘要：

  该报告继续对4-[（对氯苯基）氨基] -6-甲基-2-氧代环己基-3-烯-1-酸酯1（ADD 196022）和甲基4-（苄基氨基）进行深入评估-6-甲基-2-氧代环己基-3-烯-1-酸酯，2个，两个有效的抗惊厥性烯胺酮。这些化合物采用杏仁核点燃模型进行评估。1和2都没有针对杏仁核点燃的癫痫发作的活性，进一步支持了角膜点燃的模型作为抗电击癫痫发作评估的确定工具，如先前报道。关于1的其他腹膜内（ip）数据显示，在100 mg / kg的24小时内有毒性。为了使毒性最小化，已经制备了几种活性类似物。在由抗癫痫药物开发（ADD）计划开发的特殊ip大鼠屏幕中，对这些新的类似物进行了评估，以防最大剂量10 mg / kg的电击惊厥（MES）和100 mg / kg的神经毒性。从该筛选中，显示出几种化合物是更安全的替代品，最引人注目的是4-[（（对-溴苯基）氨基] -6-甲基-2-氧代环己基-3-en-

  DOI：

  10.1021/jm00066a003

文献信息

• Ultraviolet spectroscopy of anticonvulsant enaminones
  作者：I.O Edafiogho、O.A Phillips、M Abdel-Hamid、A.A.M Ali、W.C Matowe、A El-Hashim、S.B Kombian

  DOI：10.1016/s0968-0896(01)00314-5

  日期：2002.3

  The ultraviolet (UV) spectra of selected enaminones were determined in acidic, alkaline and neutral media and compared to their anticonvulsant activities. The wavelength of maximum absorption and molar absorptivity were compared with the anticonvulsant activity of the selected secondary and tertiary enaminones. and general inferences were made. The UV spectra of the enaminones had hypsochromic shifts in acidic media in comparison with neutral media. Generally, a small hypsochromic shift occurred in alkaline media when compared to the neutral solutions of the enaminones. The tertiary enaminones absorbed UV light at longer wavelength than the secondary enaminones in acidic, neutral and alkaline media. In particular, the tertiary enaminones displayed absorption at the higher end and secondary enaminones towards the lower end of the UV wavelength range 292-315 nm in aqueous media. Tertiary enaminones (30-33) which were devoid of the NH proton were found to be uniformly inactive in a mouse model of electroshock seizures, while some secondary enaminones (1, 5-8, 12. 16, 18, 20, 23-25, 28 and 29) had anticonvulsant activity. Thus the NH group of secondary enaminones is very important for anticonvulsant activity, and this agrees with an already established trend in proton NMR spectroscopy. In addition, the pares-substitution on the phenyl group in some enaminones result in higher molar absorptivity (a) values that enhance anticonvulsant activity. These results indicate that the anticonvulsant activity of enaminones is not due to electronic effect alone, but is probably due to a combination of factors including electronic and steric effects. lipophilicity, and hydrogen bonding. (C) 2002 Elsevier Science Ltd. All rights reserved.