(3R)-1-[(5-amino-1-benzothien-2-yl)methyl]-3-pyrrolidinol | 832103-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (3R)-1-[(5-amino-1-benzothien-2-yl)methyl]-3-pyrrolidinol
• 英文别名: 3-Pyrrolidinol, 1-[(5-aminobenzo[b]thien-2-yl)methyl]-, (3R)-；(3R)-1-[(5-amino-1-benzothiophen-2-yl)methyl]pyrrolidin-3-ol
• CAS: 832103-04-5
• 化学式: C₁₃H₁₆N₂OS
• 分子量: 248.349
• InChiKey: VKDSSQMRQBYPOD-LLVKDONJSA-N

物化性质

• 沸点：
  462.6±45.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylidene]amino}-2-thiophenecarboxylate 、 (3R)-1-[(5-amino-1-benzothien-2-yl)methyl]-3-pyrrolidinol 以 苯酚 为溶剂， 反应 1.5h， 生成 6-(4-chlorophenyl)-3-(2-{[(3R)-3-hydroxypyrrolidin-1-yl]methyl}-1-benzothien-5-yl)thieno[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  6-(4-Chlorophenyl)-3-substituted-thieno[3,2-d]pyrimidin-4(3H)-one-Based Melanin-Concentrating Hormone Receptor 1 Antagonist

  摘要：

  Genetic manipulation studies in mice at both the MCH receptor 1 (MCHR1) as well as the MCH peptide levels have implicated MCHR1 as a key player in energy homeostasis. The phenotype exhibited by these studies, that is, increased metabolic rate, resistance to high fat diet, and subsequent weight loss, has spurred considerable efforts to develop antagonists of MCHR1. In continuation of efforts directed toward this goal, the present work capitalizes on the putative binding mode of an MCH antagonist, resulting in the identification of several novel chemotypes that are potent and selective MCHR1 antagonists. In addition, the favorable pharmacokinetics of representative examples has allowed for the evaluation of an MCHR1 antagonist in a high fat diet-induced obese rodent model of obesity. The tolerability of the right-hand side of the template for diverse chemotypes accompanied by favorable effects on weight loss enhances the attractiveness of this template in the pursuit toward development of effective anti-obesity agents.

  DOI：

  10.1021/jm060814b
• 作为产物：
  描述：

  2-氯-5-硝基苯甲醛 在 Pd/C 氢氧化钾 、 lithium hydroxide 、 lithium aluminium tetrahydride 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 57.0h， 生成 (3R)-1-[(5-amino-1-benzothien-2-yl)methyl]-3-pyrrolidinol
  参考文献：
  名称：

  6-(4-Chlorophenyl)-3-substituted-thieno[3,2-d]pyrimidin-4(3H)-one-Based Melanin-Concentrating Hormone Receptor 1 Antagonist

  摘要：

  Genetic manipulation studies in mice at both the MCH receptor 1 (MCHR1) as well as the MCH peptide levels have implicated MCHR1 as a key player in energy homeostasis. The phenotype exhibited by these studies, that is, increased metabolic rate, resistance to high fat diet, and subsequent weight loss, has spurred considerable efforts to develop antagonists of MCHR1. In continuation of efforts directed toward this goal, the present work capitalizes on the putative binding mode of an MCH antagonist, resulting in the identification of several novel chemotypes that are potent and selective MCHR1 antagonists. In addition, the favorable pharmacokinetics of representative examples has allowed for the evaluation of an MCHR1 antagonist in a high fat diet-induced obese rodent model of obesity. The tolerability of the right-hand side of the template for diverse chemotypes accompanied by favorable effects on weight loss enhances the attractiveness of this template in the pursuit toward development of effective anti-obesity agents.

  DOI：

  10.1021/jm060814b