(6-溴-1-异喹啉基)氨基甲酸叔丁酯 | 552331-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: (6-溴-1-异喹啉基)氨基甲酸叔丁酯
• 中文别名: N-叔丁氧羰基-6-溴异喹啉-1-胺
• 英文名称: tert-butyl (6-bromoisoquinolin-1-yl)carbamate
• 英文别名: (6-Bromo-isoquinolin-1-yl)-carbamic acid tert-butyl ester；N-Boc-6-bromoisoquinolin-1-amine；tert-butyl N-(6-bromoisoquinolin-1-yl)carbamate
• CAS: 552331-12-1
• 化学式: C₁₄H₁₅BrN₂O₂
• 分子量: 323.189
• InChiKey: RBQZLNFQLLUPBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-溴-1-异喹啉基)氨基甲酸叔丁酯 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-{5-[(2S)-2-amino-3-(1H-indol-3-yl)propoxy]pyridin-3-yl}isoquinolin-1-amine
  参考文献：
  名称：

  Isoquinoline–pyridine-based protein kinase B/Akt antagonists: SAR and in vivo antitumor activity

  摘要：

  The structure-activity relationships of a series of isoquinoline-pyridine-based protein kinase B/Akt antagonists have been investigated in an effort to improve the major short-comings of the lead compound 3, including poor pharmacokinetic profiles in several species (e.g., mouse iv t(1/2) = 0.3 h, po F= 0%). Chlorination at C-1 position of the isoquinoline improved its pharmacokinetic property in mice (iv t(1/2) = 5.0 h, po F = 51%) but resulted in > 500-fold drop in potency. In a mouse MiaPaCa-2 xenograft model, an amino analog 10y significantly slowed the tumor growth, however was accompanied by toxicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.041
• 作为产物：
  描述：

  1-氯-6-溴异喹啉 在 乙酰胺 、 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 (6-溴-1-异喹啉基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Isoquinoline–pyridine-based protein kinase B/Akt antagonists: SAR and in vivo antitumor activity

  摘要：

  The structure-activity relationships of a series of isoquinoline-pyridine-based protein kinase B/Akt antagonists have been investigated in an effort to improve the major short-comings of the lead compound 3, including poor pharmacokinetic profiles in several species (e.g., mouse iv t(1/2) = 0.3 h, po F= 0%). Chlorination at C-1 position of the isoquinoline improved its pharmacokinetic property in mice (iv t(1/2) = 5.0 h, po F = 51%) but resulted in > 500-fold drop in potency. In a mouse MiaPaCa-2 xenograft model, an amino analog 10y significantly slowed the tumor growth, however was accompanied by toxicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.041

文献信息

• WO2022/118016
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] ENZYME INHIBITORS<br/>[FR] INHIBITEURS ENZYMATIQUES
  申请人：[en]KALVISTA PHARMACEUTICALS LIMITED

  公开号：WO2022118016A2

  公开（公告）日：2022-06-09

  The present invention provides compounds of formula (I): compositions comprising such compounds; the use of such compounds in medicine; and methods of treating patients with such compounds; wherein A, W, R5, n, Z, X, Y and B are as defined herein. The present invention also relates to compounds useful as synthetic intermediates of compounds of formula (I).