6,15-Dibromo-13-chloro-2-(1-methylpiperidin-4-yl)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ol | 213771-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并环庚烷吡啶
• 英文名称: 6,15-Dibromo-13-chloro-2-(1-methylpiperidin-4-yl)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ol
• CAS: 213771-92-7
• 化学式: C₂₀H₂₁Br₂ClN₂O
• 分子量: 500.661
• InChiKey: QQKVXZYOIVKQLM-UHFFFAOYSA-N

物化性质

• 沸点：
  540.2±50.0 °C(predicted)
• 密度：
  1.625±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,15-Dibromo-13-chloro-2-(1-methylpiperidin-4-yl)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ol 在 二溴亚砜 、 N,N-二甲基乙酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 Ethyl 4-(6,15-dibromo-13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  Bridgehead modification of trihalocycloheptabenzopyridine lead to a potent farnesyl protein transferase inhibitor with improved oral metabolic stability

  摘要：

  Modification of the ethano bridge of the core structure of the antitumor agent, SARASAR(R) (SCH66336) with concomitant introduction of a sulfonamide moiety off the distal piperidine afforded inhibitor 9-(S-), a compound with greatly improved PK profile. Other compounds with enhanced FPTase inhibitory activity were obtained as exemplified by amide 10-(S-) and urea 11-(S-): these compounds demonstrated activity in picomolar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.020
• 作为产物：
  描述：

  magnesium,1-methylpiperidin-4-ide,chloride 、 3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one 以 四氢呋喃 为溶剂， 反应 1.0h， 以60%的产率得到6,15-Dibromo-13-chloro-2-(1-methylpiperidin-4-yl)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ol
  参考文献：
  名称：

  SYNTHESIS OF INTERMEDIATES USEFUL IN PREPARING TRICYCLIC COMPOUNDS

  摘要：

  公开号：

  EP0977739B1

文献信息

• SYNTHESIS OF INTERMEDIATES USEFUL IN PREPARING TRICYCLIC COMPOUNDS
  申请人：SCHERING CORPORATION

  公开号：EP0977739B1

  公开（公告）日：2003-10-29
• Bridgehead modification of trihalocycloheptabenzopyridine lead to a potent farnesyl protein transferase inhibitor with improved oral metabolic stability
  作者：F. George Njoroge、Bancha Vibulbhan、Xiongwei Shi、Corey Strickland、Paul Kirschmeier、Robert Bishop、Amin Nomeir、Viyyoor Girijavallabhan

  DOI：10.1016/j.bmcl.2004.09.020

  日期：2004.12

  Modification of the ethano bridge of the core structure of the antitumor agent, SARASAR(R) (SCH66336) with concomitant introduction of a sulfonamide moiety off the distal piperidine afforded inhibitor 9-(S-), a compound with greatly improved PK profile. Other compounds with enhanced FPTase inhibitory activity were obtained as exemplified by amide 10-(S-) and urea 11-(S-): these compounds demonstrated activity in picomolar range. (C) 2004 Elsevier Ltd. All rights reserved.