5-methoxy-3-(pyrrolidin-3-yl)indole | 190326-15-9

• 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: 5-methoxy-3-(pyrrolidin-3-yl)indole
• 英文别名: 5-methoxy-3-pyrrolidin-3-yl-1H-indole
• CAS: 190326-15-9
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: XQPKIIGWDBNEFP-UHFFFAOYSA-N

物化性质

• 沸点：
  415.6±40.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-(pyrrolidin-3-yl)indole 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 生成 Prop-2-en-1-yl 5-methoxy-9,12-diazatetracyclo[10.2.1.0^{2,10}.0^{3,8}]pentadeca-2(10),3,5,7-tetraene-11-carboxylate
  参考文献：
  名称：

  Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.

  DOI：

  10.1016/j.bmcl.2007.05.070
• 作为产物：
  描述：

  5-甲氧基吲哚-3-甲醛 在 哌啶 、 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 5-methoxy-3-(pyrrolidin-3-yl)indole
  参考文献：
  名称：

  Structure-based design of 7-azaindole-pyrrolidine amides as inhibitors of 11β-hydroxysteroid dehydrogenase type I

  摘要：

  Indole-pyrrolidines were identified as inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) by high-throughput screening. Optimisation of the initial hit through structure-based design led to 7-azaindole-derivatives, with the best analogues displaying single digit nanomolar IC(50) potency. The modeling hypotheses were confirmed by solving the X-ray co-crystal structure of one of the lead compounds. These compounds were selective against 11β-hydroxysteroid dehydrogenase type 2 (selectivity ratio >200) and exhibited good inhibition of 11β-HSD1 (IC(50)<1μM) in a cellular model (3T3L1 adipocytes).

  DOI：

  10.1016/j.bmcl.2012.07.070

文献信息

• A Direct Synthesis of 3-(Pyrrolidin-3-yl)indoles for Use As Conformationally Restricted Analogs of Tryptamines
  作者：John E. Macor、David H. Blank、Kevin Ryan、Ronald J. Post

  DOI：10.1055/s-1997-1214

  日期：1997.4

  An efficient, two step synthesis of 3-(pyrrolidin-3-yl)indoles 4 is described. Indoles react with maleimides in refluxing acetic acid affording 3-(indol-3-yl)succinimides 6. Reaction times and yields depend on the substituents on the indole 5. Direct reduction of the succinimides 6 with LAH affords the desired conformationally restricted tryptamine derivatives 4.

  本文描述了一种 3-(吡咯烷-3-基)吲哚 4 的高效两步合成法。吲哚与马来酰亚胺在回流乙酸中反应，生成 3-(吲哚-3-基)琥珀酰亚胺 6。反应时间和产量取决于吲哚 5 上的取代基。用 LAH 直接还原琥珀酰亚胺 6，可得到所需的构象受限的色胺衍生物 4。
• Beta-carboline compounds and analogues thereof as mitogen-activated protein kinase-activated protein kinase-2 inhibitors
  申请人：Meyers J. Marvin

  公开号：US20050101623A1

  公开（公告）日：2005-05-12

  The present invention provides novel bridged beta-carboline compounds that are capable of inhibiting mitogen activated protein kinase-activated protein kinase-2 and analogues thereof and pharmaceutical compositions and kits that include these compounds.

  本发明提供了新型的桥接β-喹啉衍生物，能够抑制有丝分裂原活化蛋白激酶激活蛋白激酶-2及其类似物，并且包括这些化合物的制药组合物和试剂盒。
• [EN] INDOLE DERIVATIVES AS SEROTONERGIC AGENTS USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO<br/>[FR] DÉRIVÉS D'INDOLE UTILISÉS EN TANT QU'AGENTS SÉROTONINERGIQUES UTILES POUR LE TRAITEMENT DE TROUBLES ASSOCIÉS À CEUX-CI
  申请人：[en]MINDSET PHARMA INC.

  公开号：WO2023019367A1

  公开（公告）日：2023-02-23

  The present application relates to indole compounds of general formula I, to processes for their preparation, to compositions comprising them and to their use in activation of a serotonin receptors in a cell, as well as to treating diseases, disorders or conditions by activation of a serotonin receptors in a cell. The diseases, disorders or conditions include, for example, psychosis, mental illnesses and CNS disorders. Formula I (I) wherein Q is selected from (Q1), (Q2), (Q2'), (Q3), (Q4) and (Q5).
• Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
  作者：John I. Trujillo、Marvin J. Meyers、David R. Anderson、Shridhar Hegde、Matthew W. Mahoney、William F. Vernier、Ingrid P. Buchler、Kun K. Wu、Syaluan Yang、Susan J. Hartmann、David B. Reitz

  DOI：10.1016/j.bmcl.2007.05.070

  日期：2007.8

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.
• Structure-based design of 7-azaindole-pyrrolidine amides as inhibitors of 11β-hydroxysteroid dehydrogenase type I
  作者：Eric Valeur、Serge Christmann-Franck、Franck Lepifre、Denis Carniato、Daniel Cravo、Christine Charon、Sophie Bozec、Djordje Musil、Per Hillertz、Liliane Doare、Fabien Schmidlin、Marc Lecomte、Melanie Schultz、Didier Roche

  DOI：10.1016/j.bmcl.2012.07.070

  日期：2012.9

  Indole-pyrrolidines were identified as inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) by high-throughput screening. Optimisation of the initial hit through structure-based design led to 7-azaindole-derivatives, with the best analogues displaying single digit nanomolar IC(50) potency. The modeling hypotheses were confirmed by solving the X-ray co-crystal structure of one of the lead compounds. These compounds were selective against 11β-hydroxysteroid dehydrogenase type 2 (selectivity ratio >200) and exhibited good inhibition of 11β-HSD1 (IC(50)<1μM) in a cellular model (3T3L1 adipocytes).