tert-butyl N-[3-oxo-2-phenyl-3-[[5-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]amino]propyl]carbamate | 1159682-84-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl N-[3-oxo-2-phenyl-3-[[5-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]amino]propyl]carbamate
• CAS: 1159682-84-4
• 化学式: C₂₅H₂₆N₄O₃S
• 分子量: 462.572
• InChiKey: DOGPFYRSQFDLSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[3-oxo-2-phenyl-3-[[5-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]amino]propyl]carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到3-amino-2-phenyl-N-[5-(1H-pyrrolo[2,3-b]pyridin-4-yl)-2-thienyl]propanamide
  参考文献：
  名称：

  Discovery of 5-pyrrolopyridinyl-2-thiophenecarboxamides as potent AKT kinase inhibitors

  摘要：

  A pyrrolopyridinyl thiophene carboxamide 7 was discovered as a tractable starting point for a lead optimization effort in an AKT kinase inhibition program. SAR studies aided by a co-crystal structure of 7 in AKT2 led to the identification of AKT inhibitors with subnanomolar potency. Representative compounds showed antiproliferative activity as well as inhibition of phosphorylation of the downstream target GSK3 beta. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.094
• 作为产物：
  描述：

  在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl N-[3-oxo-2-phenyl-3-[[5-(1H-pyrrolo[2,3-b]pyridin-4-yl)thiophen-2-yl]amino]propyl]carbamate
  参考文献：
  名称：

  Discovery of 5-pyrrolopyridinyl-2-thiophenecarboxamides as potent AKT kinase inhibitors

  摘要：

  A pyrrolopyridinyl thiophene carboxamide 7 was discovered as a tractable starting point for a lead optimization effort in an AKT kinase inhibition program. SAR studies aided by a co-crystal structure of 7 in AKT2 led to the identification of AKT inhibitors with subnanomolar potency. Representative compounds showed antiproliferative activity as well as inhibition of phosphorylation of the downstream target GSK3 beta. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.094

文献信息

• [EN] INHIBITORS OF Akt ACTIVITY<br/>[FR] INHIBITEURS D'ACTIVITE Akt
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2007076423A2

  公开（公告）日：2007-07-05

  [EN] Invented are novel thiophene compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.
  [FR] La présente invention concerne des composés de thiophène atypiques, l'utilisation de tels composés comme inhibiteurs de l'activité de la protéine kinase B et pour le traitement du cancer et de l'arthrite.
• Discovery of 5-pyrrolopyridinyl-2-thiophenecarboxamides as potent AKT kinase inhibitors
  作者：Mark A. Seefeld、Meagan B. Rouse、Kenneth C. McNulty、Lihui Sun、Jizhou Wang、Dennis S. Yamashita、Juan I. Luengo、ShuYun Zhang、Elisabeth A. Minthorn、Nestor O. Concha、Dirk A. Heerding

  DOI：10.1016/j.bmcl.2009.02.094

  日期：2009.4

  A pyrrolopyridinyl thiophene carboxamide 7 was discovered as a tractable starting point for a lead optimization effort in an AKT kinase inhibition program. SAR studies aided by a co-crystal structure of 7 in AKT2 led to the identification of AKT inhibitors with subnanomolar potency. Representative compounds showed antiproliferative activity as well as inhibition of phosphorylation of the downstream target GSK3 beta. (c) 2009 Elsevier Ltd. All rights reserved.