{5-Bromo-3-[2-(3-methoxy-5-methyl-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone | 218800-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: {5-Bromo-3-[2-(3-methoxy-5-methyl-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone
• 英文别名: [5-Bromo-3-[2-(3-methoxy-5-methylphenyl)ethyl]pyridin-2-yl]-(1-methylpiperidin-4-yl)methanone
• CAS: 218800-10-3
• 化学式: C₂₂H₂₇BrN₂O₂
• 分子量: 431.373
• InChiKey: BYCFPYWCEMPPDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {5-Bromo-3-[2-(3-methoxy-5-methyl-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone 在 三氟甲磺酸 作用下， 以30%的产率得到3-Bromo-10-methoxy-8-methyl-11-(1-methyl-piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
  参考文献：
  名称：

  Analogues of 1-(3,10-Dibromo-8-chloro-6,11-dihydro-5 H -benzo[5,6]-cyclohepta[1,2- b ]pyridin-11-yl)piperidine as inhibitors of farnesyl protein transferase

  摘要：

  The synthesis of several 4-pyridylacetyl N-oxide derivatives of 4-(3-bromo-6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]-pyridin-11-yl)pi perazine/piperidine 3 is described. This study was aimed at identifying fomesyl protein transferase (FPT) inhibitors in these two series of tricycles containing different phenyl ring substituents. The in vitro activity profile of the initial group of compounds 7a-7g led to the synthesis of the 8-methyl-10-methoxy and 8-methyl-10-bromo analogues 7i, 13i, and 13j. The 11R(-) enantiomers of these compounds were found to exhibit potent in vitro FPT inhibition activity.

  DOI：

  10.1016/s0968-0896(99)00103-0
• 作为产物：
  描述：

  3-甲基-5-硝基-2-吡啶甲腈 在 盐酸 、 硫酸 、 氢溴酸 、 铁粉 、 N,N-二甲基甲酰胺 、 calcium chloride 、 lithium diisopropyl amide 、 sodium nitrite 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 水 、 甲苯 为溶剂， 反应 21.75h， 生成 {5-Bromo-3-[2-(3-methoxy-5-methyl-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone
  参考文献：
  名称：

  Analogues of 1-(3,10-Dibromo-8-chloro-6,11-dihydro-5 H -benzo[5,6]-cyclohepta[1,2- b ]pyridin-11-yl)piperidine as inhibitors of farnesyl protein transferase

  摘要：

  The synthesis of several 4-pyridylacetyl N-oxide derivatives of 4-(3-bromo-6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]-pyridin-11-yl)pi perazine/piperidine 3 is described. This study was aimed at identifying fomesyl protein transferase (FPT) inhibitors in these two series of tricycles containing different phenyl ring substituents. The in vitro activity profile of the initial group of compounds 7a-7g led to the synthesis of the 8-methyl-10-methoxy and 8-methyl-10-bromo analogues 7i, 13i, and 13j. The 11R(-) enantiomers of these compounds were found to exhibit potent in vitro FPT inhibition activity.

  DOI：

  10.1016/s0968-0896(99)00103-0

文献信息

• Analogues of 1-(3,10-Dibromo-8-chloro-6,11-dihydro-5 H -benzo[5,6]-cyclohepta[1,2- b ]pyridin-11-yl)piperidine as inhibitors of farnesyl protein transferase
  作者：Adriano Afonso、Jay Weinstein、Joseph Kelly、Ronald Wolin、Stuart B. Rosenblum、Michael Connolly、Timothy Guzi、Linda James、Donna Carr、Robert Patton、W.Robert Bishop、Paul Kirshmeier、M. Liu、L. Heimark、K.J. Chen、A.A. Nomeir

  DOI：10.1016/s0968-0896(99)00103-0

  日期：1999.9

  The synthesis of several 4-pyridylacetyl N-oxide derivatives of 4-(3-bromo-6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]-pyridin-11-yl)pi perazine/piperidine 3 is described. This study was aimed at identifying fomesyl protein transferase (FPT) inhibitors in these two series of tricycles containing different phenyl ring substituents. The in vitro activity profile of the initial group of compounds 7a-7g led to the synthesis of the 8-methyl-10-methoxy and 8-methyl-10-bromo analogues 7i, 13i, and 13j. The 11R(-) enantiomers of these compounds were found to exhibit potent in vitro FPT inhibition activity.