1-(8-Benzyl-7-hydroxy-1-methyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone | 851477-85-5

• 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: 1-(8-Benzyl-7-hydroxy-1-methyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone
• 英文别名: N-trifluoroacetyl-8-benzyl-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol；1-(7-benzyl-8-hydroxy-5-methyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-2,2,2-trifluoroethanone
• CAS: 851477-85-5
• 化学式: C₂₀H₂₀F₃NO₂
• 分子量: 363.38
• InChiKey: QHADNNHTMPCSHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(8-Benzyl-7-hydroxy-1-methyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 8-benzyl-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol
  参考文献：
  名称：

  Discovery and SAR of new benzazepines as potent and selective 5-HT2C receptor agonists for the treatment of obesity

  摘要：

  We report on the synthesis, biological evaluation and structure-activity relationships for a series of 3-benzazepine derivatives as 5-HT2C receptor agonists. The compounds were evaluated in functional assays measuring [H-3] phosphoinositol turnover in HEK-293 cells transiently transfected with h5-HT2C, h5-HT2A or h5-HT2B receptors. Several compounds are shown to be potent and selective 5-HT2C receptor agonists, which decrease food intake in a rat feeding model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.080
• 作为产物：
  描述：

  N-trifluoroacetyl-7-methoxy-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 氢气 、 三溴化硼 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1-(8-Benzyl-7-hydroxy-1-methyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone
  参考文献：
  名称：

  Discovery and SAR of new benzazepines as potent and selective 5-HT2C receptor agonists for the treatment of obesity

  摘要：

  We report on the synthesis, biological evaluation and structure-activity relationships for a series of 3-benzazepine derivatives as 5-HT2C receptor agonists. The compounds were evaluated in functional assays measuring [H-3] phosphoinositol turnover in HEK-293 cells transiently transfected with h5-HT2C, h5-HT2A or h5-HT2B receptors. Several compounds are shown to be potent and selective 5-HT2C receptor agonists, which decrease food intake in a rat feeding model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.080

文献信息

• [EN] BENZAZEPINE DERIVATIVES AND METHODS OF PROPHYLAXIS OR TREATMENT OF 5HT2C RECEPTOR ASSOCIATED DISEASES<br/>[FR] DERIVES DE BENZAZEPINE ET METHODES DE PROPHYLAXIE OU TRAITEMENT DE MALADIES ASSOCIEES AU RECEPTEUR 5HT2C
  申请人：ARENA PHARM INC

  公开号：WO2005042491A1

  公开（公告）日：2005-05-12

  The present invention relates to substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives that are modulators of the 5HT2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.

  本发明涉及替代的2,3,4,5-四氢-3-苯并哌啶衍生物，它们是5HT2C受体的调节剂。因此，本发明的化合物对于预防或治疗与5HT2C受体相关的疾病、症状或障碍，如肥胖及相关疾病，具有用处。
• Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2c Receptor Associated Diseases
  申请人：Smith Brian

  公开号：US20080009478A1

  公开（公告）日：2008-01-10

  The present invention relates to substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives that are modulators of the 5HT 2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT 2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.

  本发明涉及替代的2,3,4,5-四氢-3-苯并氮平衍生物，其是5HT2C受体的调节剂。因此，本发明的化合物对于预防或治疗与5HT2C受体相关的疾病、状况或障碍，例如肥胖症及相关障碍，具有用途。
• Discovery and SAR of new benzazepines as potent and selective 5-HT2C receptor agonists for the treatment of obesity
  作者：Brian M. Smith、Jeffrey M. Smith、James H. Tsai、Jeffrey A. Schultz、Charles A. Gilson、Scott A. Estrada、Rita R. Chen、Douglas M. Park、Emily B. Prieto、Charlemagne S. Gallardo、Dipanjan Sengupta、William J. Thomsen、Hazel R. Saldana、Kevin T. Whelan、Frederique Menzaghi、Robert R. Webb、Nigel R.A. Beeley

  DOI：10.1016/j.bmcl.2004.12.080

  日期：2005.3

  We report on the synthesis, biological evaluation and structure-activity relationships for a series of 3-benzazepine derivatives as 5-HT2C receptor agonists. The compounds were evaluated in functional assays measuring [H-3] phosphoinositol turnover in HEK-293 cells transiently transfected with h5-HT2C, h5-HT2A or h5-HT2B receptors. Several compounds are shown to be potent and selective 5-HT2C receptor agonists, which decrease food intake in a rat feeding model. (c) 2005 Elsevier Ltd. All rights reserved.