2-(5-methoxy-1-methyl-1H-indol-3-yl)propanoic acid | 92059-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(5-methoxy-1-methyl-1H-indol-3-yl)propanoic acid
• 英文别名: 2-(5-methoxy-1-methylindol-3-yl)propanoic acid
• CAS: 92059-79-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: QPFKORXBWDPRGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-methoxy-1-methyl-1H-indol-3-yl)propanoic acid 在 lithium aluminium tetrahydride 、 三乙胺 、 氯甲酸甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (+/-)-1,Beta-Dimethylmelatonin
  参考文献：
  名称：

  Mapping the Melatonin Receptor. 7. Subtype Selective Ligands Based on β-Substituted N-Acyl-5-methoxytryptamines and β-Substituted N-Acyl-5-methoxy-1-methyltryptamines

  摘要：

  A series of beta-substituted and beta,beta-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxy-tryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT(1) and MT(2) receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. beta-Methylmelatonin ( 17a) and beta,beta-dimethylmelatonin ( 17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus. N-Butanoyl 5-methoxy-1-methyl-beta,beta-trimethylenetryptamine ( 12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-beta,beta-tetramethylenetryptamine ( 13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.

  DOI：

  10.1021/jm0512544
• 作为产物：
  描述：

  2-(5-Methoxy-1-methyl-1H-indol-3-yl)-propionic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以5.20 g的产率得到2-(5-methoxy-1-methyl-1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Mapping the Melatonin Receptor. 7. Subtype Selective Ligands Based on β-Substituted N-Acyl-5-methoxytryptamines and β-Substituted N-Acyl-5-methoxy-1-methyltryptamines

  摘要：

  A series of beta-substituted and beta,beta-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxy-tryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT(1) and MT(2) receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. beta-Methylmelatonin ( 17a) and beta,beta-dimethylmelatonin ( 17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus. N-Butanoyl 5-methoxy-1-methyl-beta,beta-trimethylenetryptamine ( 12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-beta,beta-tetramethylenetryptamine ( 13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.

  DOI：

  10.1021/jm0512544

文献信息

• Substituted Heteroaromatic Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
  申请人：Frank Robert

  公开号：US20120115903A1

  公开（公告）日：2012-05-10

  Substituted heteroaromatic carboxamide and urea compounds corresponding to formula (i) processes for the preparation thereof, pharmaceutical compositions containing these compounds and also a method of using these compounds in pharmaceutical compositions for treating or inhibiting pain and other conditions mediated at least in part via the vanilloid receptor 1.

  将与式（i）对应的取代杂芳基羧酰胺和脲化合物翻译成中文，以及其制备方法、含有这些化合物的药物组合物，以及在药物组合物中使用这些化合物治疗或抑制至少部分通过辣椒素受体1介导的疼痛和其他症状的方法。
• [EN] SUBSTITUTED HETEROAROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS<br/>[FR] CARBOXAMIDE HÉTÉROAROMATIQUE SUBSTITUÉ ET DÉRIVÉS DE L'URÉE EN TANT QUE LIGANDS DU RÉCEPTEUR VANILLOÏDE
  申请人：GRUENENTHAL GMBH

  公开号：WO2012062462A1

  公开（公告）日：2012-05-18

  The invention relates to substituted heteroaromatic carboxamide and urea derivatives of formula (I), to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.

  这项发明涉及公式（I）的取代杂环羧酰胺和脲衍生物，涉及其制备方法，含有这些化合物的药物组合物，以及利用这些化合物制备药物组合物。
• HETEROCYCLIC AZA COMPOUNDS
  申请人：Grünenthal GmbH

  公开号：EP3130589A1

  公开（公告）日：2017-02-15

  The invention relates to heterocyclic aza compounds as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  本发明涉及杂环氮化物作为vanilloid受体配体，含有这些化合物的制药组合物，以及这些化合物用于治疗和/或预防疼痛和其他疾病和/或障碍的用途。
• SUBSTITUTED HETEROAROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
  申请人：Grünenthal GmbH

  公开号：EP2638034A1

  公开（公告）日：2013-09-18