(E)-N-[(1R)-1-(3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)prop-2-enamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-[(1R)-1-(3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)prop-2-enamide
• 化学式: C₁₉H₁₉FN₂O₂
• 分子量: 326.37
• InChiKey: KJKISBSTHVUMEV-BUUCAEBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N-[(1R)-1-(3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)prop-2-enamide 在 potassium carbonate 、 肼 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 (R)-1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethylamine
  参考文献：
  名称：

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzooxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide is a potent and efficacious KCNQ2 opener which inhibits induced hyperexcitability of rat hippocampal neurons

  摘要：

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide ((S)-2) was identified as a potent and efficacious KCNQ2 opener. This compound demonstrated significant activity in reducing neuronal hyperexcitability in rat hippocampal slices, and the inhibition mediated by (S)-2 was reversed by the KCNQ blocker linopirdine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.069
• 作为产物：
  描述：

  6-乙酰基-2H-1,4-苯并噁嗪-3(4H)-酮 在 镍 4-二甲氨基吡啶 、 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0 ℃ 、344.74 kPa 条件下， 生成 (E)-N-[(1R)-1-(3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)prop-2-enamide
  参考文献：
  名称：

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzooxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide is a potent and efficacious KCNQ2 opener which inhibits induced hyperexcitability of rat hippocampal neurons

  摘要：

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide ((S)-2) was identified as a potent and efficacious KCNQ2 opener. This compound demonstrated significant activity in reducing neuronal hyperexcitability in rat hippocampal slices, and the inhibition mediated by (S)-2 was reversed by the KCNQ blocker linopirdine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.069

文献信息

• (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzooxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide is a potent and efficacious KCNQ2 opener which inhibits induced hyperexcitability of rat hippocampal neurons
  作者：Yong-Jin Wu、Christopher G Boissard、Jie Chen、William Fitzpatrick、Qi Gao、Valentin K Gribkoff、David G Harden、Huan He、Ronald J Knox、Joanne Natale、Rick L Pieschl、John E Starrett、Li-Qiang Sun、Mark Thompson、David Weaver、Dedong Wu、Steven I Dworetzky

  DOI：10.1016/j.bmcl.2004.01.069

  日期：2004.4

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide ((S)-2) was identified as a potent and efficacious KCNQ2 opener. This compound demonstrated significant activity in reducing neuronal hyperexcitability in rat hippocampal slices, and the inhibition mediated by (S)-2 was reversed by the KCNQ blocker linopirdine. (C) 2004 Elsevier Ltd. All rights reserved.