5-Amino-2-pyrrolidinomethyl-benzothiophen | 96750-34-4

• 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: 5-Amino-2-pyrrolidinomethyl-benzothiophen
• 英文别名: [2-(1-pyrrolidinylmethyl)-1-benzothien-5-yl]amine；2-pyrrolidin-1-ylmethylbenzo[b]thiophen-5-ylamine；2-(Pyrrolidin-1-ylmethyl)-1-benzothiophen-5-amine
• CAS: 96750-34-4
• 化学式: C₁₃H₁₆N₂S
• 分子量: 232.349
• InChiKey: BSWCPGLZAYULAV-UHFFFAOYSA-N

物化性质

• 沸点：
  396.7±27.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 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：
  57.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylidene]amino}-2-thiophenecarboxylate 、 5-Amino-2-pyrrolidinomethyl-benzothiophen 以 苯酚 为溶剂， 反应 1.5h， 生成 6-(4-chlorophenyl)-3-[2-(1-pyrrolidinylmethyl)-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 5-Amino-2-pyrrolidinomethyl-benzothiophen
  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

文献信息

• Aminoalkyl-substituted aromatic bicyclic compounds, methods for their preparation and their use as pharmaceuticals
  申请人：——

  公开号：US20030212070A1

  公开（公告）日：2003-11-13

  The present invention relates to aminoalkyl-substituted aromatic bicyclic compounds of formula I, 1 which are valuable pharmaceutically active compounds that are suitable, for example, for the treatment of obesity, type II diabetes, arteriosclerosis, high blood pressure, paresthesia, depression, anxiety, anxiety neuroses, schizophrenia, disorders associated with the circadian rhythm, and drug abuse, as well as normalizing lipid metabolism.

  本发明涉及公式I的氨基烷基取代芳香双环化合物，这些化合物是有价值的药用活性化合物，例如适用于治疗肥胖症、2型糖尿病、动脉硬化、高血压、感觉异常、抑郁症、焦虑症、焦虑神经症、精神分裂症、与昼夜节律相关的疾病以及药物滥用，同时还能正常化脂质代谢。
• AMINOALKYL SUBSTITUIERTE AROMATISCHE BICYCLEN, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS ARZNEIMITTEL
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1418906A1

  公开（公告）日：2004-05-19
• [DE] AMINOALKYL SUBSTITUIERTE AROMATISCHE BICYCLEN, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS ARZNEIMITTEL<br/>[EN] AMINOALKYL-SUBSTITUTED AROMATIC BICYCLIC COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICAMENTS<br/>[FR] COMPOSES BICYCLIQUES AROMATIQUES A SUBSTITUTION AMINOALKYLE, PROCEDES DE PRODUCTION DE CES COMPOSES ET LEUR UTILISATION EN TANT QUE MEDICAMENTS
  申请人：AVENTIS PHARMA GMBH

  公开号：WO2003015769A1

  公开（公告）日：2003-02-27

  Die Erfindung betrifft Aminoalkyl substituierte aromatische Bicyclen sowie deren physiologisch verträgliche Salze und physiologisch funktionelle Derivate. Es werden Verbindungen der Formel (I), worin die Reste die angegebenen Bedeutungen haben, sowie deren physiologisch verträglichen Salze und Verfahren zu deren Herstellung beschrieben. Die Verbindungen eignen sich z.B. als Anorektika.
• 6-(4-Chlorophenyl)-3-substituted-thieno[3,2-<i>d</i>]pyrimidin-4(3<i>H</i>)-one-Based Melanin-Concentrating Hormone Receptor 1 Antagonist
  作者：Francis X. Tavares、Kamal A. Al-Barazanji、Michael J. Bishop、Christy S. Britt、David L. Carlton、Joel P. Cooper、Paul L. Feldman、Dulce M. Garrido、Aaron S. Goetz、Mary K. Grizzle、Donald L. Hertzog、Diane M. Ignar、Daniel G. Lang、Maggie S. McIntyre、Ronda J. Ott、Andrew J. Peat、Hui-Qiang Zhou

  DOI：10.1021/jm060814b

  日期：2006.11.30

  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.