2-(4-(benzyloxy)-1H-indol-3-yl)ethanamine | 109249-04-9

• 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-(4-(benzyloxy)-1H-indol-3-yl)ethanamine
• 英文别名: 4-benzyloxytryptamine；2-(4-benzyloxy-indol-3-yl)-ethylamine；2-(4-Benzyloxy-indol-3-yl)-aethylamin；4-(Benzyloxy)-1H-indole-3-ethanamine；2-(4-phenylmethoxy-1H-indol-3-yl)ethanamine
• CAS: 109249-04-9
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: KSDRYRLZDHZMDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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-(4-(benzyloxy)-1H-indol-3-yl)ethanamine 在 sodium dihydrogenphosphate 、 potassium nitrososulfonate 、 palladium 10% on activated carbon 、 氢气 、 四丁基硫酸氢铵 、 magnesium 、 三乙胺 、 potassium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 97.0h， 生成 tert-butyl (2-(1,1-dioxido-5,9-dioxo-2,3,4,5,6,9-hexahydro-[1,4]thiazino[2,3-f]indol-8-yl)ethyl)(methyl)carbamate
  参考文献：
  名称：

  Total Synthesis of Thiaplakortone A: Derivatives as Metabolically Stable Leads for the Treatment of Malaria

  摘要：

  Thiaplakortone A (3a), an antimalarial natural product, was prepared by an operationally simple and scalable synthesis. In our efforts to deliver a lead compound with improved potency, metabolic stability, and selectivity, the synthesis was diverted to access a series of analogues. Compounds, 3a-d showed nanomolar activity against the chloroquine-sensitive (3D7) Plasmodium falciparum line and were more active against the chloroquine- and mefloquine-resistant (Dd2) P. falciparum line. All compounds are "Rule-of-5" compliant, and we show that metabolic stability can be enhanced via modification at either the primary or pyrrole nitrogen. These promising results lay the foundation for the development of this structurally unprecedented natural product.

  DOI：

  10.1021/ml400447v
• 作为产物：
  描述：

  4-苄氧基吲哚 在 lithium aluminium tetrahydride 、 乙醚 、 乙醇 、 溶剂黄146 、 碘甲烷 作用下， 生成 2-(4-(benzyloxy)-1H-indol-3-yl)ethanamine
  参考文献：
  名称：

  Eine neue合成von Bufotenin和verwandten Oxy-tryptaminen。40.米特伊龙·尤伯·穆特尔恩·科纳洛德

  摘要：

  Es wird eine rationelle合成了Bufotenin和Andereω-N-取代基5-羟基色胺Angegeben。羟基-色胺-维他命合剂：5-Oxy-ω-N-甲基-胰蛋白酶，5-Oxy-ω-N-乙基-胰蛋白酶，5-Oxy-ω-N，N-二乙基-胰蛋白酶，5-Oxy-ω-N-β-氨基萘基-胰蛋白酶，N- [β-（5-Oxy-吲哚基-（3））-th基]-哌啶，二羟色胺素，DAS 4-Oxy-tryptamin und das 6-Oxy-tryptamin。

  DOI：

  10.1002/hlca.19550380619

文献信息

• [EN] 3-(2-(AMINOETHYL)-INDOL-4-OL DERIVATIVES, METHODS OF PREPARATION THEREOF, AND THE USE AS 5-HT2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE 3-(2-(AMINOÉTHYL)-INDOL-4-OL, LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION EN TANT QUE MODULATEURS DU RÉCEPTEUR 5-HT2
  申请人：BRIGHT MINDS BIOSCIENCES INC

  公开号：WO2021179091A1

  公开（公告）日：2021-09-16

  A compound of Formula I, which possesses 5-HT2A and/or 5-HT2c selective receptor activity, but lacks at least some of the undesirable characteristics of 5-HT2B-agonist related activities, is disclosed. Methods of preparing said compounds are also described. The compound of Formula I may be useful in the treatment of depression, alcoholism, tobacco and cocaine addiction, inflammation, cluster headache, PTSD, seizure disorders and other CNS disorders.

  公开了一种具有5-HT2A和/或5-HT2c选择性受体活性但缺乏至少一些不良特性的5-HT2B激动剂相关活性的化合物I的化合物。还描述了制备所述化合物的方法。化合物I的化合物可能在治疗抑郁症、酒精中毒、吸烟和可卡因成瘾、炎症、集群头痛、创伤后应激障碍、癫痫和其他中枢神经系统疾病方面有用。
• Synthetic Studies of Psilocin Analogs Having Either a Formyl Group or Bromine Atom at the 5- or 7-Position.
  作者：Fumio Yamada、Mayumi Tamura、Atsuko Hasegawa、Masanori Somei

  DOI：10.1248/cpb.50.92

  日期：——

  Psilocin analogs having either a formyl group (9—12) or a bromine atom (13—18) at the 5- or 7-position have been prepared for the first time. Syntheses of 5- and 7-bromo derivatives of 4-hydroxy- (23, 24, 28) and 4-benzyloxyindole-3-carbaldehyde (19, 25, 29, 30), 4-benzyloxyindole-3-acetonitriles (20, 31), and 4-benzyloxy-N, N-dimethyltryptamine (32, 34, 35) have also been established.

  首次合成了在5位或7位具有甲酰基（9—12）或溴原子（13—18）的Psilocin类似物。此外，还建立了4-羟基（23, 24, 28）和4-苄氧吲哚-3-甲醛（19, 25, 29, 30）、4-苄氧吲哚-3-乙腈（20, 31）以及4-苄氧-N,N-二甲基色氨酸（32, 34, 35）的5-和7-溴衍生物的合成方法。
• Gold-Catalyzed Asymmetric Intramolecular Cyclization of N-Allenamides for the Synthesis of Chiral Tetrahydrocarbolines
  作者：Yidong Wang、Peichao Zhang、Xiaoyu Di、Qiang Dai、Zhan-Ming Zhang、Junliang Zhang

  DOI：10.1002/anie.201709595

  日期：2017.12.11

  Ringing the changes: The first example of highly enantioselective gold-catalyzed intramolecular cyclization of N-allenamides was implemented by utilizing PC-Phos ligands. The utility of this reaction was validated by the total synthesis of (R)-desbromoarborescidine A.

  顺应变化：利用PC-Phos配体实现了N-allenamides的高对映选择性金催化的分子内环化的第一个例子。该反应的实用性通过（R）-desbromoarborescidine A的全合成得到验证。
• Highly Enantioselective Bromocyclization of Tryptamines and Its Application in the Synthesis of (−)-Chimonanthine
  作者：Weiqing Xie、Guangde Jiang、Huan Liu、Jiadong Hu、Xixian Pan、Hui Zhang、Xiaolong Wan、Yisheng Lai、Dawei Ma

  DOI：10.1002/anie.201306774

  日期：2013.12.2

  A shorter path: A highly enantioselective bromocyclization of tryptamine has been developed using an anionic chiral phase‐transfer catalyst. This method provides a direct approach for preparing chiral 3‐bromopyrroloindoline from tryptamine, which enables a four‐step enantioselective synthesis of (−)‐chimonanthine. PG=protecting group.

  较短的路径：使用阴离子手性相转移催化剂开发了对色胺的高度对映选择性溴环化反应。该方法为从色胺中制备手性3-溴吡咯并吲哚啉提供了一种直接方法，该方法可实现（-）-烟酰胺嘌呤的四步对映选择性合成。PG ＝保护基。
• [EN] NITRATED PSILOCYBIN DERIVATIVES AND USE THEREOF FOR MODULATING 5-HT2A RECEPTOR AND FOR TREATING A PSYCHIATRIC DISORDER<br/>[FR] DÉRIVÉS NITRÉS DE PSILOCYBINE ET UTILISATION ASSOCIÉE POUR LA MODULATION DU RÉCEPTEUR 5-HT2A ET POUR LE TRAITEMENT D'UN TROUBLE PSYCHIATRIQUE
  申请人：MAGICMED IND INC

  公开号：WO2022047583A1

  公开（公告）日：2022-03-10

  Disclosed are nitrated psilocybin compounds of formula (I), wherein at least one of R2, R4, R5, R6, or R7, is a nitro group, and wherein each non-nitrated R2, R5, R6, or R7, is a hydrogen atom, an alkyl, O-alkyl or O-aryl group, wherein R4 when it is not nitrated is a hydrogen atom, an alkyl, O-alkyl or O-aryl group, a hydroxy group, or a phosphate group, and wherein R3a, and R3b, are a hydrogen atom, an alkyl group, an aryl group, or an acyl group, pharmaceutical formulations containing the same. The nitrated psilocybin compounds of formula (I) may be chemically synthesized or biochemically synthesized in host cells. The nitrated compounds of formula (I) may be used for modulating 5-HT2A receptor, and for treating a psychiatric disorder in a subject.

  本发明涉及一种公式（I）的硝化哌醋酸衍生物，其中R2、R4、R5、R6或R7中至少有一个是硝基，且每个未硝化的R2、R5、R6或R7是氢原子、烷基、O-烷基或O-芳基基团，当R4未硝化时，它是氢原子、烷基、O-烷基或O-芳基基团、羟基或磷酸酯基团，而R3a和R3b是氢原子、烷基、芳基或酰基团，制备这种化合物的制剂。公式（I）的硝化哌醋酸衍生物可以在宿主细胞中化学合成或生物化学合成。公式（I）的硝化化合物可用于调节5-HT2A受体，并用于治疗受试者的精神障碍。