1-[4-(3-bromo-8-chloro-5H-[1]benzoxepino[4,3-b]pyridin-11-ylidene)piperidin-1-yl]-2-(1-oxidopyridin-1-ium-4-yl)ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 1-[4-(3-bromo-8-chloro-5H-[1]benzoxepino[4,3-b]pyridin-11-ylidene)piperidin-1-yl]-2-(1-oxidopyridin-1-ium-4-yl)ethanone
• 化学式: C₂₅H₂₁BrClN₃O₃
• 分子量: 526.817
• InChiKey: ZRMWHAYAESKTOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 4-(8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-1-piperidine-carboxylate 在 盐酸 、 氢溴酸 、 溴 、 四丁基硝酸铵 、 铁粉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸酐 、 calcium chloride 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 1-[4-(3-bromo-8-chloro-5H-[1]benzoxepino[4,3-b]pyridin-11-ylidene)piperidin-1-yl]-2-(1-oxidopyridin-1-ium-4-yl)ethanone
  参考文献：
  名称：

  Inhibitors of farnesyl protein transferase. synthesis and biological activity of amide and cyanoguanidine derivatives containing a 5,11-dihydro[1]benzthiepin, benzoxepin, and benzazepin [4,3-b]pyridine ring system

  摘要：

  Bioisosteric replacement of the C-6 carbon atom in piperidine I and piperazine II with S, O, and N heteroatoms is described. Amide and cyanoguanidine derivatives of these compounds were evaluated in vitro and found to be good inhibitors of farnesyl-protein transferase. An improved method of preparing the 5,11-dihydro-[1]-benzthiepin nucleus 6 was accomplished in high yield and with excellent regioselectivity using an AlCl3 melt protocol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00439-9

文献信息

• Inhibitors of farnesyl protein transferase. synthesis and biological activity of amide and cyanoguanidine derivatives containing a 5,11-dihydro[1]benzthiepin, benzoxepin, and benzazepin [4,3-b]pyridine ring system
  作者：Ronald Wolin、Michael Connolly、Joseph Kelly、Jay Weinstein、Stuart Rosenblum、Adriano Afonso、Linda James、Paul Kirschmeier、W. Robert Bishop

  DOI：10.1016/s0960-894x(98)00439-9

  日期：1998.9

  Bioisosteric replacement of the C-6 carbon atom in piperidine I and piperazine II with S, O, and N heteroatoms is described. Amide and cyanoguanidine derivatives of these compounds were evaluated in vitro and found to be good inhibitors of farnesyl-protein transferase. An improved method of preparing the 5,11-dihydro-[1]-benzthiepin nucleus 6 was accomplished in high yield and with excellent regioselectivity using an AlCl3 melt protocol. (C) 1998 Elsevier Science Ltd. All rights reserved.