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 | 433692-66-1

• 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: 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
• CAS: 433692-66-1
• 化学式: C₂₂H₂₁Br₂ClN₂O₂
• 分子量: 540.682
• InChiKey: BCGPEBPVPBSMQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  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 在 N-甲基吗啉 、 盐酸 、 乙胺嗪 、 碳酸氢钠 、 1-羟基苯并三唑 、 三氟乙酸 作用下， 生成 4-[2-[4-[(2R)-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]piperidin-1-yl]-2-oxoethyl]piperidine-1-carboxamide
  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：

  N-methyl-4-piperidinylmagnesium bromide 在 二溴亚砜 、 N,N-二甲基乙酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 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

文献信息

• 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.