(S)-2-(6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidin]-3-yl)-2-methylpropanoic acid hydrochloride | 1243675-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (S)-2-(6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidin]-3-yl)-2-methylpropanoic acid hydrochloride
• CAS: 1243675-13-9
• 化学式: C₁₈H₂₄ClNO₂*ClH
• 分子量: 358.308
• InChiKey: AWWNIPSYHYSNLU-UQKRIMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-叔丁基-4-(2,4-二氟苯基)吡咯烷-3-羧酸 、 (S)-2-(6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidin]-3-yl)-2-methylpropanoic acid hydrochloride 、 (S)-3-吡咯烷醇 在 N-甲基吗啉 、 N-羟基-7-氮杂苯并三氮唑 、 HATU 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(1S)-1'-[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carbonyl]-5-chloro-6-methylspiro[1,2-dihydroindene-3,4'-piperidine]-1-yl]-1-[(3S)-3-hydroxypyrrolidin-1-yl]-2-methylpropan-1-one
  参考文献：
  名称：

  Spiroindane based amides as potent and selective MC4R agonists for the treatment of obesity

  摘要：

  We report a series of potent and selective MC4R agonists based on spiroindane amide privileged structures for potential treatments of obesity. Among the synthetic methods used, Method C allows rapid synthesis of the analogs. The series of compounds can afford high potency on MC4R as well as good rodent pharmacokinetic profiles. Compound 1r (MK-0489) demonstrates MC4R mediated reduction of food intake and body weight in mouse models. Compound 1r is efficacious in 14-day diet-induced obese (DIO) rat models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.062
• 作为产物：
  描述：

  2-[(1S)-5-chloro-6-methyl-1'-[(2-methylpropan-2-yl)oxycarbonyl]spiro[1,2-dihydroindene-3,4'-piperidine]-1-yl]-2-methylpropanoic acid 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (S)-2-(6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidin]-3-yl)-2-methylpropanoic acid hydrochloride
  参考文献：
  名称：

  Spiroindane based amides as potent and selective MC4R agonists for the treatment of obesity

  摘要：

  We report a series of potent and selective MC4R agonists based on spiroindane amide privileged structures for potential treatments of obesity. Among the synthetic methods used, Method C allows rapid synthesis of the analogs. The series of compounds can afford high potency on MC4R as well as good rodent pharmacokinetic profiles. Compound 1r (MK-0489) demonstrates MC4R mediated reduction of food intake and body weight in mouse models. Compound 1r is efficacious in 14-day diet-induced obese (DIO) rat models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.062