5-cyclohexyl-1-(2,4-dichlorophenyl)-3-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one | 503842-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-cyclohexyl-1-(2,4-dichlorophenyl)-3-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one
• 英文别名: 5-cyclohexyl-1-(2,4-dichlorophenyl)-3-methyl-6,7-dihydropyrrolo[3,2-c]pyridin-4-one
• CAS: 503842-35-1
• 化学式: C₂₀H₂₂Cl₂N₂O
• 分子量: 377.313
• InChiKey: ZNCQSMLTVWIXRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-cyclohexyl-1-(2,4-dichlorophenyl)-3-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以98%的产率得到
  参考文献：
  名称：

  Constrained analogs of CB-1 antagonists: 1,5,6,7-Tetrahydro-4H-pyrrolo[3,2-c]pyridine-4-one derivatives

  摘要：

  A series of pyrrolopyridinones was designed and synthesized as constrained analogs of the pyrazole CB-1 antagonist rimonabant. Certain examples exhibited very potent hCB-1 receptor binding affinity and functional antagonism with Ki and Kb values below 10 nM, and with high selectivity for CB-1 over CB-2 (> 100-fold). A representative analog was established to cause significant appetite suppression and reduction in body weight gain in industry-standard rat models used to develop new therapeutics for obesity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.095
• 作为产物：
  描述：

  1-(2,4-二氯苯基氨基)丙烷-2-酮 、 1-cyclohexylpiperidine-2,4-dione 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 5-cyclohexyl-1-(2,4-dichlorophenyl)-3-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one
  参考文献：
  名称：

  Constrained analogs of CB-1 antagonists: 1,5,6,7-Tetrahydro-4H-pyrrolo[3,2-c]pyridine-4-one derivatives

  摘要：

  A series of pyrrolopyridinones was designed and synthesized as constrained analogs of the pyrazole CB-1 antagonist rimonabant. Certain examples exhibited very potent hCB-1 receptor binding affinity and functional antagonism with Ki and Kb values below 10 nM, and with high selectivity for CB-1 over CB-2 (> 100-fold). A representative analog was established to cause significant appetite suppression and reduction in body weight gain in industry-standard rat models used to develop new therapeutics for obesity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.095

文献信息

• Preparation and use of 1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine derivatives for treatment of obesity
  申请人：——

  公开号：US20040224970A1

  公开（公告）日：2004-11-11

  This invention relates to 1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine derivatives which have been found to suppress appetite and induce weight loss. The invention also provides methods for synthesis of the compounds, pharmaceutical compositions comprising the compounds, and methods of using such compositions for inducing weight loss and treating obesity and obesity-related disorders.

  本发明涉及1,5,6,7-四氢吡咯并[3,2-c]吡啶衍生物，已发现其能够抑制食欲并引起减重。该发明还提供了合成该化合物的方法，包含该化合物的药物组合物，以及使用这种组合物诱导减重和治疗肥胖和肥胖相关疾病的方法。
• Preparation and use of 1,5,6,7-tetrahydropyrrolo[3,2-C]pyridine derivatives for the treatment of obesity
  申请人：Smith A. Roger

  公开号：US20060122215A1

  公开（公告）日：2006-06-08

  This invention relates to 1,5,6,7-tetrahydropynolo[3,2-c]pyridine derivatives which have been found to suppress appetite and induce weight loss. The invention also provides methods for synthesis of the compounds, pharmaceutical compositions comprising the compounds, and methods of using such compositions for inducing weight loss and treating obesity and obesity-related disorders.

  本发明涉及1,5,6,7-四氢吡啶并[3,2-c]吡啶衍生物，发现其具有抑制食欲和诱导减重的作用。本发明还提供了合成该化合物的方法，包括该化合物的制药组合物，以及使用这样的组合物诱导减重和治疗肥胖及相关疾病的方法。
• PREPARATION AND USE OF 1,5,6,7-TETRAHYDROPYRROLO 3,2-C]PYRIDINE DERIVATIVES FOR TREATMENT OF OBESITY
  申请人：Bayer Pharmaceuticals Corporation

  公开号：EP1432708B1

  公开（公告）日：2005-11-30
• US7071207B2
  申请人：——

  公开号：US7071207B2

  公开（公告）日：2006-07-04
• Constrained analogs of CB-1 antagonists: 1,5,6,7-Tetrahydro-4H-pyrrolo[3,2-c]pyridine-4-one derivatives
  作者：Roger A. Smith、Zahra Fathi、Su-Ellen Brown、Soongyu Choi、Jianmei Fan、Susan Jenkins、Harold C.E. Kluender、Anish Konkar、Rico Lavoie、Ronald Mays、Jennifer Natoli、Stephen J. O’Connor、Astrid A. Ortiz、Brent Podlogar、Christy Taing、Susan Tomlinson、Theresa Tritto、Zhonghua Zhang

  DOI：10.1016/j.bmcl.2006.10.095

  日期：2007.2

  A series of pyrrolopyridinones was designed and synthesized as constrained analogs of the pyrazole CB-1 antagonist rimonabant. Certain examples exhibited very potent hCB-1 receptor binding affinity and functional antagonism with Ki and Kb values below 10 nM, and with high selectivity for CB-1 over CB-2 (> 100-fold). A representative analog was established to cause significant appetite suppression and reduction in body weight gain in industry-standard rat models used to develop new therapeutics for obesity. (c) 2006 Elsevier Ltd. All rights reserved.