5-bromo-2-methyltryptamine hydrochloride

• 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: 5-bromo-2-methyltryptamine hydrochloride
• 英文别名: 2-(5-bromo-2-methyl-1H-indol-3-yl)ethanamine Hydrochloride；2-(5-bromo-2-methyl-1H-indol-3-yl)ethanamine;hydrochloride
• 化学式: C₁₁H₁₃BrN₂*ClH
• 分子量: 289.603
• InChiKey: QGCQZGODBUZGSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  41.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-2-methyltryptamine hydrochloride 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 tert-butyl (2-(1-benzyl-5-bromo-2-methyl-1H-indol-3-yl)ethyl)carbamate
  参考文献：
  名称：

  Synthesis and cytotoxic properties of tryptamine derivatives

  摘要：

  The cyclopropyliminium and subsequent Grandberg rearrangements of cyclopropylketone hydrozones lead to the formation of tryptamines, which were additionally substituted at either the aromatic ring atoms or the amino group. The products were tested for their cytotoxic properties against HepG2, Jurkat and HEK293 cell lines using MTT assay. The highest activity as well as the highest selectivity was found amongst the compounds derived with one benzyl substituent at the amino group. The flow cytometry technique revealed cell-type specificity in terms of the mechanism of viability inhibition. Thus, the compounds were found to induce mainly apoptosis in HEK293 and HepG2 cells, while Jurkat cells displayed late apoptotic and necrotic responses. The apoptosis pathway is most likely to include mitochondrial damage. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.070
• 作为产物：
  描述：

  环丙甲基酮 、 4-溴苯肼盐酸盐 以 乙醇 为溶剂， 反应 7.0h， 以80%的产率得到5-bromo-2-methyltryptamine hydrochloride
  参考文献：
  名称：

  The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines

  摘要：

  The cyclopropyliminium rearrangement of cyclopropylketone arylhydrazones may result in two possible products. The first one forms via cyclopropane ring-opening and ring-closure to give six-membered tetrahydropyridazines. The second is formed via ring-closure resulting in a five-membered ring and subsequent Grandberg rearrangement into a tryptamine. The product ratio depends on the nature of the starting hydrazones. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.017

文献信息

• [EN] 5-HALO-TRYPTAMINE DERIVATIVES USED AS LIGANDS OF THE 5-HT6 AND/OR 5-HT7 SEROTONIN RECEPTORS<br/>[FR] DERIVES DE 5-HALO-TRYPTAMINE UTILISES COMME LIGANDS DES RECEPTEURS SEROTONINERGIQUES 5-HT6 ET/OU 5-HT7
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2003000252A1

  公开（公告）日：2003-01-03

  Compounds of Formula (I): (I); wherein: R1 and R2 either the same or different, are H or linear or branched C1-C6 alkyl; R3 = linear or branched C1-C6 alkyl; R4 = halogen, and pharmaceutically acceptable salts thereof are useful as active ingredients in the preparation of medicaments used as ligands of the 5-HT6 and/or 5-HT7 serotoninergic receptors.

  化合物的化学式（I）：（I）；其中：R1和R2相同或不同，是氢或线性或支链的C1-C6烷基；R3 = 线性或支链的C1-C6烷基；R4 = 卤素，其药学上可接受的盐在制备用作5-HT6和/或5-HT7血清素受体配体的药物的活性成分中有用。
• 5-halo-tryptamine derivatives used as ligands of the 5-ht6 and/or 5-ht7 serotonin receptors
  申请人：——

  公开号：US20040235899A1

  公开（公告）日：2004-11-25

  Compounds of Formula (I): (I); wherein: R 1 and R 2 either the same or different, are H or linear or branched C 1 -C 6 alkyl; R 3 =linear or branched C 1 -C 6 alkyl; R 4 =halogen, and pharmaceutically acceptable salts thereof are useful as active ingredients in the preparation of medicaments used as ligands of the 5-HT 6 and/or 5-HT 7 serotoninergic receptors.

  公式为（I）的化合物：（I）; 其中：R1和R2相同或不同，是氢或线性或支链C1-C6烷基; R3 = 线性或支链C1-C6烷基; R4 = 卤素，其药学上可接受的盐在制备用作5-HT6和/或5-HT7 5-羟色胺受体配体的药物的活性成分时是有用的。
• 5-HALO-TRYPTAMINE DERIVATIVES USED AS LIGANDS OF THE 5-HT 6? AND/OR 5-HT 7? SEROTONIN RECEPTORS
  申请人：SIGMA-TAU IndustrieFarmaceutiche Riunite S.p.A.

  公开号：EP1404317A1

  公开（公告）日：2004-04-07
• US7098233B2
  申请人：——

  公开号：US7098233B2

  公开（公告）日：2006-08-29
• The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines
  作者：Rinat F. Salikov、Aleksandr Yu. Belyy、Yury V. Tomilov

  DOI：10.1016/j.tetlet.2014.09.017

  日期：2014.10

  The cyclopropyliminium rearrangement of cyclopropylketone arylhydrazones may result in two possible products. The first one forms via cyclopropane ring-opening and ring-closure to give six-membered tetrahydropyridazines. The second is formed via ring-closure resulting in a five-membered ring and subsequent Grandberg rearrangement into a tryptamine. The product ratio depends on the nature of the starting hydrazones. (C) 2014 Elsevier Ltd. All rights reserved.