2-(5-methoxy-1H-indol-3-yl)-2-methylpropane-1-amine | 948053-93-8

• 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-1H-indol-3-yl)-2-methylpropane-1-amine
• 英文别名: 2-(5-methoxy-1H-indol-3-yl)-2-methylpropan-1-amine
• CAS: 948053-93-8
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: RDXJZGGKAQSDSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-methoxy-1H-indol-3-yl)-2-methylpropane-1-amine 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 19.0h， 生成 tert-butyl 6-methoxy-2,4,4-trimethyl-1-oxo-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-9-carboxylate
  参考文献：
  名称：

  The discovery of carboline analogs as potent MAPKAP-K2 inhibitors

  摘要：

  The discovery of a series of potent, carboline-based MK2 inhibitors is described. These compounds inhibit MK2 with IC(50)s as low as 10 nM, as measured in a DELFIA assay. An X-ray crystal structure reveals that they bind in a region near the p-loop and the hinge region of MK2a. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.101
• 作为产物：
  描述：

  5-甲氧基-A,A-二甲基-1H-吲哚-3-乙腈 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 0.75h， 生成 2-(5-methoxy-1H-indol-3-yl)-2-methylpropane-1-amine
  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

• 吲哚衍生物及其在药物上的应用
  申请人：广东东阳光药业有限公司

  公开号：CN104496985B

  公开（公告）日：2016-09-14

  本发明提供一系列吲哚类衍生物或其立体异构体，互变异构体，氮氧化物，代谢产物，药学上可接受的盐或前药，其可用作激动褪黑素受体激动剂。本发明还公开了含有这样的化合物的药物组合物，以及使用本发明化合物或其药物组合物治疗哺乳动物，特别是人类中枢神经系统功能障碍的用途。
• Process for the chemical resolution of 5-alkoxy-substituted (+/-)-1,3-dimethyloxindolylethylamines
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0418770A2

  公开（公告）日：1991-03-27

  A process for chemically resolving a mixture of enantiomers of primary amines, such as enantiomers of 1,3-dimethyl-5-methoxyoxindolylethylamine, provides one of the enantiomers in the form of a tartaric acid salt. In carrying out the process, an enantiomeric mixture is contacted with a chiral acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The resulting precipitate can then be recovered. The chiral acid is selected from the group consisting of dibenzoyl-D-tartaric acid, dibenzoyl-L-tartaric acid, ditoluoyl-D-tartaric acid, and ditoluoyl-L-tartaric acid. The precipitates can be used in the synthesis of stereospecific forms of physostigmine.

  一种对伯胺对映体混合物（如 1,3-二甲基-5-甲氧基吲哚乙胺的对映体）进行化学分解的工艺可提供酒石酸盐形式的其中一种对映体。在实施该工艺时，将对映体混合物与手性酸接触，接触量足以优先沉淀出手性酸和其中一种对映体的盐。然后回收沉淀物。手性酸选自二苯甲酰基-D-酒石酸、二苯甲酰基-L-酒石酸、二托洛尔-D-酒石酸和二托洛尔-L-酒石酸组成的组。沉淀物可用于合成立体特异形式的酞丁斯的明。