3-(2-氨基乙基)-1H-吲哚-5,7-二醇 | 31363-74-3

• 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
• 中文名称: 3-(2-氨基乙基)-1H-吲哚-5,7-二醇
• 中文别名: 5,7-二甲氧基色胺
• 英文名称: 5,7-dihydroxytryptamine
• 英文别名: 5,7-DHT；3-(2-aminoethyl)-1H-indole-5,7-diol
• CAS: 31363-74-3
• 化学式: C₁₀H₁₂N₂O₂
• mdl: MFCD05260760
• 分子量: 192.217
• InChiKey: LXWHQTNFZDTKBH-UHFFFAOYSA-N

物化性质

• 沸点：
  479.6±30.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.3
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(2-氨基乙基)-1H-吲哚-5,7-二醇 在 盐酸 作用下， 生成 5-hydroxytryptamine-4,7-dione monohydrochloride
  参考文献：
  名称：

  Oxidation of 5-hydroxytryptamine and 5,7-dihydroxytryptamine. A new oxidation pathway and formation of a novel neurotoxin

  摘要：

  The electrochemical oxidation of 5-hydroxytryptamine (5-HT) in acidic solution proceeds through a minor route leading first to 5,7-dihydroxytryptamine (5,7-DHT) then to 4,5,7-trihydroxytryptamine and finally to 5-hydroxytryptamine-4,7-dione. The latter compound is a major electrochemical oxidation product of 5,7-DHT at pH 2 and 7 and a major autoxidation product at pH greater than or equal to 6. Preliminary biological results indicate that 5-hydroxytryptamine-4,7-dione is a more potent central nervous system toxin than 5,7-DHT. These results show for the first time a chemical pathway from 5-HT to 5,7-DHT and suggest possible minor metabolic oxidative pathways for the neurotransmitter 5-HT to at least two powerful neurotoxins.

  DOI：

  10.1021/jm00154a013
• 作为产物：
  描述：

  5-羟基色胺 生成 3-(2-氨基乙基)-1H-吲哚-5,7-二醇
  参考文献：
  名称：

  WRONA, M. Z.;LEMORDANT, D.;LIN, L.;BLANK, C. LEROY;DRYHURST, G., J. MED. CHEM., 1986, 29, N 4, 499-505

  摘要：

  DOI：

文献信息

• HEXAHYDRODIAZEPINOQUINOLINES CARRYING A CYCLIC RADICAL
  申请人：AbbVie Deutschland GmbH & Co. KG

  公开号：US20150259343A1

  公开（公告）日：2015-09-17

  The present invention relates to tricyclic hexahydrodiazepinoquinolines carrying a cyclic substituent, to a method for producing them, to a pharmaceutical composition containing such compounds, to their use as modulators, especially agonists or partial agonists, of the 5-HT 2C receptor, their use for preparing a medicament for the prevention or treatment of conditions and disorders which respond to the modulation of 5-HT 2C receptor, to a method for preventing or treating conditions and disorders which respond to the modulation of 5-HT 2C receptor, and processes for preparing such compounds and compositions.

  本发明涉及携带环状取代基的三环六氢二氮杂喹啉类化合物，以及生产它们的方法，含有这类化合物的药物组合物，它们作为5-HT2C受体的调节剂，特别是激动剂或部分激动剂的用途，用于制备用于预防或治疗对5-HT2C受体调节产生反应的疾病和疾病的药物，用于预防或治疗对5-HT2C受体调节产生反应的疾病和疾病的方法，以及制备这类化合物和组合物的方法。
• TRICYCLIC QUINOLINE AND QUINOXALINE DERIVATIVES
  申请人：ABBVIE DEUTSCHLAND GMBH & CO. KG

  公开号：US20140080813A1

  公开（公告）日：2014-03-20

  The present invention relates to tricyclic quinoline and quinoxaline derivatives, to a pharmaceutical composition containing such compounds, to their use as modulators, especially agonists or partial agonists, of the 5-HT 2C receptor, their use for preparing a medicament for the prevention or treatment of conditions and disorders which respond to the modulation of 5-HT 2C receptor, and to a method for preventing or treating conditions and disorders which respond to the modulation of 5-HT 2C receptor.

  本发明涉及三环喹啉和喹啉衍生物，涉及含有这些化合物的药物组合物，以及它们作为5-HT2C受体调节剂，特别是激动剂或部分激动剂的用途，用于制备用于预防或治疗对5-HT2C受体调节有反应的病症和紊乱的药物，以及用于预防或治疗对5-HT2C受体调节有反应的病症和紊乱的方法。
• Chemical and enzyme-mediated oxidation of the serotonergic neurotoxin 5,7-dihydroxytryptamine: mechanistic insights
  作者：Tahereh Tabatabaie、Glenn Dryhurst

  DOI：10.1021/jm00090a018

  日期：1992.6

  Because of its enormous basicity O2- facilitates deprotonation of 1. The C(4)-centered carbanion so produced is oxidized by molecular O2 or by the hydroperoxy radical (HO2) to give radical intermediates and thence 2 and 3. Mechanistic pathways leading to the various products of oxidation of 1 are proposed and the potential roles of oxidation reactions of the indolamine are related to its neurodegenerative

  在生理pH条件下，在厌氧和好氧条件下，研究了5-羟色胺神经毒素5,7-二羟基色胺（1）的氧化化学和生物化学。在厌氧条件下，单电子氧化剂（铁细胞色素c，过氧化物酶/ H2O2，铜蓝蛋白，Cu2 +）产生自由基中间体。此自由基的C（6）中心共振形式的二聚反应，然后进行二次氧化，生成3-（2-氨基乙基）-6- [3-（2-氨基乙基）-1,7-二氢-5-羟基-7-氧代-6H-吲哚-6-亚烷基] -1-H-吲哚-5,7（4H，6H）-二酮。在有氧条件下，分子O2攻击以C（4）为中心的1自由基，产生氢过氧自由基，该自由基分解为5-羟基色胺-4,7-二酮（2）。1的自动氧化过程由分子O2对以C（4）为中心的碳负离子的主要攻击进行，从而形成超氧化物自由基复合物。这重新排列成一个以C（4）为中心的氢过氧化物，它分解为2。以AC（6）为中心的碳负离子与1相结合，最终得到6,6'-bi-5-hydroxytryptamine-4
• Autoxidation of the serotonergic neurotoxin 5,7-dihydroxytryptamine
  作者：Tahereh Tabatabaie、Monika Z. Wrona、Glenn Dryhurst

  DOI：10.1021/jm00164a032

  日期：1990.2

  The indolic neurotoxin 5,7-dihydroxytryptamine (5,7-DHT) has been widely speculated to express its neurodegenerative effects as a result of intraneuronol autoxidation. Until recently, it was believed that autoxidation led to reactive electrophilic quinone imine species which alkylated neuronal membrane proteins and that byproducts of the autoxidation reaction were cytotoxic reduced-oxygen species.

  吲哚神经毒素5,7-二羟基色胺（5,7-DHT）已被广泛认为可表达其神经变性，这是由于神经内自氧化作用引起的。直到最近，据信自氧化作用导致使神经元膜蛋白烷基化的反应性亲电醌亚胺种类，而自氧化反应的副产物是细胞毒性的还原氧种类。这项研究表明，在生理pH值下，5,7-DHT的碳负离子充当主要的电子给体，以1：2的比例生成以C（4）和C（6）为中心的自由基超氧化物复合物。以C（4）为中心的复合物反应生成最终的5-羟基色胺-4,7-二酮，该物质已被证明比5,7-DHT具有更强大的神经毒素。以C（6）为中心的自由基超氧化物络合物反应生成6,6'-双（5-羟基色胺4）7-dione）。后者反应很可能产生O2-作为细胞毒性副产物。
• MODULATORS OF 5-HT RECEPTORS AND METHODS OF USE THEREOF
  申请人：Akritopoulou-Zanze Irini

  公开号：US20110118231A1

  公开（公告）日：2011-05-19

  The present application relates to aryl- and heteroaryl-fused decahydropyrroloazepine, octahydrooxepinopyrrole, octahydropyrrolothiazepine dioxide, decahydrocyclohepta[c]pyrrole, and octahydrocyclohepta[c]pyrrole derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , A, Y 1 , Y 2 , and Y 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, processes for making such compounds, and methods of treating disease conditions using such compounds and compositions, and methods for identifying such compounds.

  本申请涉及公式（I）的芳基和杂环芳基融合的十氢吡咯-氮杂环庚烷、八氢氧杂环吡咯、八氢吡咯硫杂环庚烷二氧化物、十氢环庚烷[c]吡咯和八氢环庚烷[c]吡咯衍生物，其中R1、R2、R3、R4、R5、A、Y1、Y2和Y3如规范中所定义。本申请还涉及包含这些化合物的组合物、制备这些化合物的方法、使用这些化合物和组合物治疗疾病状况的方法，以及识别这些化合物的方法。