Butyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate | 1116066-84-2

• 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: Butyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate
• CAS: 1116066-84-2
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: WHQQGCATHISHMV-UHFFFAOYSA-N

物化性质

• 沸点：
  500.3±50.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Butyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate 、 对氟苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 butyl 3-(4-fluorobenzoyl)-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate
  参考文献：
  名称：

  Discovery of XL335 (WAY-362450), a Highly Potent, Selective, and Orally Active Agonist of the Farnesoid X Receptor (FXR)

  摘要：

  Azepino[4,5-b]indoles have been identified as potent agonists of the farnesoid X receptor (FXR). In vitro and in vivo optimization has led to the discovery of 6m (XL335, WAY-362450) as a potent, selective, and orally bioavailable FXR agonist (EC(50) = 4 nM, Eff = 149%). Oral administration of 6m to LDLR(-/-) mice results in lowering of cholesterol and triglycerides. Chronic administration in an atherosclerosis model results in significant reduction in aortic arch lesions.

  DOI：

  10.1021/jm8014124
• 作为产物：
  描述：

  butyl bromopyruvate 、 色胺盐酸盐 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 Butyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate
  参考文献：
  名称：

  Discovery of XL335 (WAY-362450), a Highly Potent, Selective, and Orally Active Agonist of the Farnesoid X Receptor (FXR)

  摘要：

  Azepino[4,5-b]indoles have been identified as potent agonists of the farnesoid X receptor (FXR). In vitro and in vivo optimization has led to the discovery of 6m (XL335, WAY-362450) as a potent, selective, and orally bioavailable FXR agonist (EC(50) = 4 nM, Eff = 149%). Oral administration of 6m to LDLR(-/-) mice results in lowering of cholesterol and triglycerides. Chronic administration in an atherosclerosis model results in significant reduction in aortic arch lesions.

  DOI：

  10.1021/jm8014124

文献信息

• Discovery of XL335 (WAY-362450), a Highly Potent, Selective, and Orally Active Agonist of the Farnesoid X Receptor (FXR)
  作者：Brenton Flatt、Richard Martin、Tie-Lin Wang、Paige Mahaney、Brett Murphy、Xiao-Hui Gu、Paul Foster、Jiali Li、Parinaz Pircher、Mary Petrowski、Ira Schulman、Stefan Westin、Jay Wrobel、Grace Yan、Eric Bischoff、Chris Daige、Raju Mohan

  DOI：10.1021/jm8014124

  日期：2009.2.26

  Azepino[4,5-b]indoles have been identified as potent agonists of the farnesoid X receptor (FXR). In vitro and in vivo optimization has led to the discovery of 6m (XL335, WAY-362450) as a potent, selective, and orally bioavailable FXR agonist (EC(50) = 4 nM, Eff = 149%). Oral administration of 6m to LDLR(-/-) mice results in lowering of cholesterol and triglycerides. Chronic administration in an atherosclerosis model results in significant reduction in aortic arch lesions.