7-(4-butyl-benzenesulfonylamino)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester | 956102-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7-(4-butyl-benzenesulfonylamino)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester
• CAS: 956102-17-3
• 化学式: C₂₅H₃₄N₂O₄S
• 分子量: 458.622
• InChiKey: RIKHQKVBUGOCCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-(4-butyl-benzenesulfonylamino)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester 在 盐酸 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 4-butyl-N-(3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)benzenesulfonamide
  参考文献：
  名称：

  Studies towards the identification of a new generation of atypical antipsychotic agents

  摘要：

  A rational structure-activity relationship study around compound (1) is reported. The lead optimisation programme led to the identification of sulfonamide (25), a molecule combining dopamine D-2/D-3 receptor antagonism with serotonin 5-HT2A, 5-HT2C, 5-HT6 receptor antagonism for an effective treatment of schizophrenia. Compound (25) was shown to possess the required in vivo activity with no EPS liability. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.036
• 作为产物：
  描述：

  3-BOC-7-氨基-1,2,4,5-四氢苯并[D]氮杂卓 、 4-正丁基苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80%的产率得到7-(4-butyl-benzenesulfonylamino)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Studies towards the identification of a new generation of atypical antipsychotic agents

  摘要：

  A rational structure-activity relationship study around compound (1) is reported. The lead optimisation programme led to the identification of sulfonamide (25), a molecule combining dopamine D-2/D-3 receptor antagonism with serotonin 5-HT2A, 5-HT2C, 5-HT6 receptor antagonism for an effective treatment of schizophrenia. Compound (25) was shown to possess the required in vivo activity with no EPS liability. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.036

文献信息

• The discovery and optimisation of benzazepine sulfonamide and sulfones as potent agonists of the motilin receptor
  作者：James M. Bailey、Jackie S. Scott、Jonathan B. Basilla、Victoria J. Bolton、Izzy Boyfield、David G. Evans、Etienne Fleury、Tom D. Heightman、Emma M. Jarvie、Kirk Lawless、Kim L. Matthews、Fiona McKay、Hindy Mok、Alison Muir、Barry S. Orlek、Gareth J. Sanger、Geoffrey Stemp、Alexander J. Stevens、Mervyn Thompson、John Ward、Kalindi Vaidya、Susan M. Westaway

  DOI：10.1016/j.bmcl.2009.09.027

  日期：2009.11

  Optimisation of a series of benzazepine sulfonamide hit compounds identified from high throughput screening led to the discovery of a new series of tractable, potent motilin receptor agonists. (C) 2009 Elsevier Ltd. All rights reserved.