N-[(1S)-1-(Benzo[b]thiophen-3-ylmethyl)-2-hydroxyethyl](tert-butoxy)carboxamide | 552330-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-[(1S)-1-(Benzo[b]thiophen-3-ylmethyl)-2-hydroxyethyl](tert-butoxy)carboxamide
• 英文别名: 1,1-dimethylethyl[(1S)-2-(1-benzothien-3-yl)-1-(hydroxymethyl)ethyl]carbamate；tert-butyl N-[(2S)-1-(1-benzothiophen-3-yl)-3-hydroxypropan-2-yl]carbamate
• CAS: 552330-21-9
• 化学式: C₁₆H₂₁NO₃S
• 分子量: 307.414
• InChiKey: HKRMPTMVIRBZJP-LBPRGKRZSA-N

物化性质

• 沸点：
  497.4±40.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(1S)-1-(Benzo[b]thiophen-3-ylmethyl)-2-hydroxyethyl](tert-butoxy)carboxamide 在 四(三苯基膦)钯 、 六甲基二锡 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 {1-benzo[b]thiophen-3-ylmethyl-2-[5-(3-methyl-1H-indazol-5-yl)-pyridin-3-yloxy]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Identification of a novel 3,5-disubstituted pyridine as a potent, selective, and orally active inhibitor of Akt1 kinase

  摘要：

  Based on lead compounds 2 and 3 a series of 3,5-disubstituted pyridines have been designed and evaluated for inhibition of AKT/PKB. Modifications at the 3 position of the pyridine ring led to a number of potent compounds with improved physical properties, resulting in the identification of 11g as a promising, orally active Akt inhibitor. The synthesis, structure-activity relationship studies, and pharmacokinetic data are presented in this paper. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.046
• 作为产物：
  描述：

  N-叔丁氧羰基-L-3-苯并噻吩丙氨酸 在 BH₃*THF 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N-[(1S)-1-(Benzo[b]thiophen-3-ylmethyl)-2-hydroxyethyl](tert-butoxy)carboxamide
  参考文献：
  名称：

  [EN] INHIBITORS OF AKT ACTIVITY
  [FR] INHIBITEURS DE L'ACTIVITE DE LA PROTEINE KINASE B (AKT)

  摘要：

  发明了新型的吡啶化合物，以及这些化合物作为PKB/AKT激酶活性的抑制剂以及用于治疗癌症和关节炎的用途。

  公开号：

  WO2005085227A1

文献信息

• Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith
  申请人：D'Sidocky Neil R.

  公开号：US20080242694A1

  公开（公告）日：2008-10-02

  Provided herein are Heterocyclic Compounds having the following structure: wherein R 1 , R 2 , X, Y and Z are as defined herein, compositions comprising an effective amount of a Heterocyclic Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heterocyclic Compound to a patient in need thereof.

  本文提供具有以下结构的杂环化合物： 其中R1、R2、X、Y和Z如本文所定义，包含有效量杂环化合物的组合物，以及治疗或预防癌症、炎症性疾病、免疫疾病、代谢性疾病以及通过给予患者需要的有效量杂环化合物来抑制激酶途径治疗或预防的疾病的方法。
• Inhibitors of akt activity
  申请人：Yamashita S. Dennis

  公开号：US20070185152A1

  公开（公告）日：2007-08-09

  Invented are novel pyridine compounds, the use of such compounds as inhibitors of PKB/AKT kinase activity and in the treatment of cancer and arthritis.

  发明了新型吡啶化合物，这些化合物可用作PKB/AKT激酶活性的抑制剂，并用于癌症和关节炎的治疗。
• 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
  作者：Qun Li、Tongmei Li、Gui-Dong Zhu、Jianchun Gong、Akiyo Claibone、Chris Dalton、Yan Luo、Eric F. Johnson、Yan Shi、Xuesong Liu、Vered Klinghofer、Joy L. Bauch、Kennan C. Marsh、Jennifer J. Bouska、Shannon Arries、Ron De Jong、Tilman Oltersdorf、Vincent S. Stoll、Clarissa G. Jakob、Saul H. Rosenberg、Vincent L. Giranda

  DOI：10.1016/j.bmcl.2005.12.017

  日期：2006.3

  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.
• Identification of a novel 3,5-disubstituted pyridine as a potent, selective, and orally active inhibitor of Akt1 kinase
  作者：Sheela A. Thomas、Tongmei Li、Keith W. Woods、Xiaohong Song、Garrick Packard、John P. Fischer、Robert B. Diebold、Xuesong Liu、Yan Shi、Vered Klinghofer、Eric F. Johnson、Jennifer J. Bouska、Amanda Olson、Ran Guan、Shayna R. Magnone、Kennan Marsh、Yan Luo、Saul H. Rosenberg、Vincent L. Giranda、Qun Li

  DOI：10.1016/j.bmcl.2006.04.046

  日期：2006.7

  Based on lead compounds 2 and 3 a series of 3,5-disubstituted pyridines have been designed and evaluated for inhibition of AKT/PKB. Modifications at the 3 position of the pyridine ring led to a number of potent compounds with improved physical properties, resulting in the identification of 11g as a promising, orally active Akt inhibitor. The synthesis, structure-activity relationship studies, and pharmacokinetic data are presented in this paper. (c) 2006 Elsevier Ltd. All rights reserved.
• [EN] INHIBITORS OF AKT ACTIVITY<br/>[FR] INHIBITEURS DE L'ACTIVITE DE LA PROTEINE KINASE B (AKT)
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005085227A1

  公开（公告）日：2005-09-15

  Invented are novel pyridine compounds, the use of such compounds as inhibitors of PKB/AKT kinase activity and in the treatment of cancer and arthritis.

  发明了新型的吡啶化合物，以及这些化合物作为PKB/AKT激酶活性的抑制剂以及用于治疗癌症和关节炎的用途。