((S)-1-(1H-Indol-3-ylmethyl)-2-{5-[(E)-2-(2-indol-1-yl-pyridin-4-yl)-vinyl]-pyridin-3-yloxy}-ethyl)-carbamic acid tert-butyl ester | 882170-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ((S)-1-(1H-Indol-3-ylmethyl)-2-{5-[(E)-2-(2-indol-1-yl-pyridin-4-yl)-vinyl]-pyridin-3-yloxy}-ethyl)-carbamic acid tert-butyl ester
• CAS: 882170-49-2
• 化学式: C₃₆H₃₅N₅O₃
• 分子量: 585.706
• InChiKey: UVYHCTVKTFGMJI-SYJLOCQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((S)-1-(1H-Indol-3-ylmethyl)-2-{5-[(E)-2-(2-indol-1-yl-pyridin-4-yl)-vinyl]-pyridin-3-yloxy}-ethyl)-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1S)-1-(1H-Indol-3-ylmethyl)-2-{5-[2-(2-indol-1-yl-pyridin-4-yl)-vinyl]-pyridin-3-yloxy}-ethylamine
  参考文献：
  名称：

  Discovery of trans-3,4′-bispyridinylethylenes as potent and novel inhibitors of protein kinase B (PKB/Akt) for the treatment of cancer: Synthesis and biological evaluation

  摘要：

  A novel series of Akt/PKB inhibitors derived from a screening lead (1) has been prepared. The novel trans-3,4'-bispyridinylethylenes described herein are potent inhibitors of Akt/PKB with IC50 values in the low double-digit nanomolar range against Akt1. Compound 2q shows excellent selectivity against distinct families of kinases such as tyrosine kinases and CAMK, and displays poor to modest selectivity against closely related kinases in the AGC and CMGC families. The cellular activities including inhibition of cell growth and phosphorylation of downstream target GSK3 are also described. The X-ray structure of compound 2q complexed with PKA in the ATP binding site was determined. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.017
• 作为产物：
  描述：

  2-氟吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 、 三(邻甲基苯基)磷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 ((S)-1-(1H-Indol-3-ylmethyl)-2-{5-[(E)-2-(2-indol-1-yl-pyridin-4-yl)-vinyl]-pyridin-3-yloxy}-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of trans-3,4′-bispyridinylethylenes as potent and novel inhibitors of protein kinase B (PKB/Akt) for the treatment of cancer: Synthesis and biological evaluation

  摘要：

  A novel series of Akt/PKB inhibitors derived from a screening lead (1) has been prepared. The novel trans-3,4'-bispyridinylethylenes described herein are potent inhibitors of Akt/PKB with IC50 values in the low double-digit nanomolar range against Akt1. Compound 2q shows excellent selectivity against distinct families of kinases such as tyrosine kinases and CAMK, and displays poor to modest selectivity against closely related kinases in the AGC and CMGC families. The cellular activities including inhibition of cell growth and phosphorylation of downstream target GSK3 are also described. The X-ray structure of compound 2q complexed with PKA in the ATP binding site was determined. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.017