7-methoxyindole-3-glyoxyl chloride | 50656-47-8

• 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: 7-methoxyindole-3-glyoxyl chloride
• 英文别名: 7-Methoxy-3-indol-glyoxylchlorid；2-(7-methoxy-1H-indol-3-yl)-2-oxoacetyl chloride
• CAS: 50656-47-8
• 化学式: C₁₁H₈ClNO₃
• 分子量: 237.642
• InChiKey: HOFMRJTYEWFTOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  7-methoxyindole-3-glyoxyl chloride 在 lithium aluminium tetrahydride 、 氨 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 2-(7-甲氧基-1H-吲哚-3-基)乙基氯化铵
  参考文献：
  名称：

  Alpha-ethyltryptamines as dual dopamine–serotonin releasers

  摘要：

  The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were > 10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.062
• 作为产物：
  描述：

  1-(3-甲氧基-2-硝基苯基)-2-硝基乙醇 在 palladium on activated charcoal 氢气 、 sodium acetate 、 乙酸酐 作用下， 以 乙醚 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 1.08h， 生成 7-methoxyindole-3-glyoxyl chloride
  参考文献：
  名称：

  乙二腈的合成

  摘要：

  提出了一种新型的昆虫拒食剂二甲状腺素（1）的有效合成方法。

  DOI：

  10.1016/s0040-4039(00)77496-x

文献信息

• Studies of New Indole Alkaloid Coupling Methods for the Synthesis of Haplophytine
  作者：Pankaj D. Rege、Yuan Tian、E. J. Corey

  DOI：10.1021/ol061319c

  日期：2006.7.1

  [reaction: see text] The two novel bisindole alkaloid structures shown can be synthesized in a few steps from the canthiphytine derivative 9.

  [反应：见正文]所示的两个新颖的双吲哚生物碱结构可通过邻苯二酚衍生物9分几步合成。
• Novel, potent and selective cyclin D1/CDK4 inhibitors: indolo[6,7-a]pyrrolo[3,4-c]carbazoles
  作者：Thomas A. Engler、Kelly Furness、Sushant Malhotra、Concha Sanchez-Martinez、Chuan Shih、Walter Xie、Guoxin Zhu、Xun Zhou、Scott Conner、Margaret M. Faul、Kevin A. Sullivan、Stanley P. Kolis、Harold B. Brooks、Bharvin Patel、Richard M. Schultz、Tammy B. DeHahn、Kashif Kirmani、Charles D. Spencer、Scott A. Watkins、Eileen L. Considine、Jack A. Dempsey、Catherine A. Ogg、Nancy B. Stamm、Bryan D. Anderson、Robert M. Campbell、Vasu Vasudevan、Michelle L. Lytle

  DOI：10.1016/s0960-894x(03)00461-x

  日期：2003.7

  The synthesis and CDK inhibitory properties of a series of indolo[6,7-a]pyrrolo[3,4-c]carbazoles is reported. In addition to their potent CDK activity, the compounds display antiproliferative activity against two human cancer cell lines. These inhibitors also effect strong G1 arrest in these cell lines and inhibit Rb phosphorylation at Ser780 consistent with inhibition of cyclin D1/CDK4.

  报道了一系列吲哚[6，7-a]吡咯并[3，4-c]咔唑的合成和CDK抑制性能。这些化合物除了具有强大的CDK活性外，还具有针对两种人类癌细胞系的抗增殖活性。这些抑制剂还影响这些细胞系中的强G1阻滞，并抑制Ser780处的Rb磷酸化，这与抑制细胞周期蛋白D1 / CDK4一致。
• Inhibitors of HIV-1 attachment. Part 2: An initial survey of indole substitution patterns
  作者：Nicholas A. Meanwell、Owen B. Wallace、Haiquan Fang、Henry Wang、Milind Deshpande、Tao Wang、Zhiwei Yin、Zhongxing Zhang、Bradley C. Pearce、Jennifer James、Kap-Sun Yeung、Zhilei Qiu、J.J. Kim Wright、Zheng Yang、Lisa Zadjura、Donald L. Tweedie、Suresh Yeola、Fang Zhao、Sunanda Ranadive、Brett A. Robinson、Yi-Fei Gong、Hwei-Gene Heidi Wang、Wade S. Blair、Pei-Yong Shi、Richard J. Colonno、Pin-fang Lin

  DOI：10.1016/j.bmcl.2009.02.040

  日期：2009.4

  inhibitor of the interaction between HIV gp120 and host cell CD4 receptors, on activity in an HIV entry assay was examined. Small substituents at C-4 generally resulted in increased potency whilst substitution at C-7 was readily tolerated and uniformly produced more potent HIV entry inhibitors. Substituents deployed at C-6 and, particularly, C-5 generally produced a modest to marked weakening of potency

  将简单的卤素，烷基和烷氧基取代基引入1-（4-苯甲酰基哌嗪-1-基）-2-（1 H检测了HIV gp120和宿主细胞CD4受体之间相互作用的抑制剂-吲哚-3-基）乙烷-1,2-二酮对HIV进入检测活性的抑制作用。C-4处的小取代基通常会提高效力，而C-7处的取代很容易被接受，并且会均匀产生更有效的HIV进入抑制剂。与原型相比，部署在C-6（尤其是C-5）上的替代品通常会产生一定程度的效力减弱。N-1处的小烷基取代基对活性的影响最小，同时增加了烷基部分的大小，导致抑制性能逐渐降低。这些研究建立了对HIV附着抑制剂药效团的吲哚成分的基本理解。
• N-(Indol-3-ylglyoxylyl)piperidines: high affinity agonists of human GABA-A receptors containing the α1 subunit
  作者：Ian Collins、William B Davey、Michael Rowley、Kathleen Quirk、Frances A Bromidge、Ruth M McKernan、Sally-Anne Thompson、Keith A Wafford

  DOI：10.1016/s0960-894x(00)00245-6

  日期：2000.6

  A new class of N-(indol-3-ylglyoxylyl)piperidines are high affinity agonists at the benzodiazepine binding site of human GABA-A receptor ion-channels, with modest selectivity for receptors containing the alpha(1) subunit over alpha(2) and alpha(3). All three receptor subtypes discriminate substantially between the two enantiomers of the chiral ligand 10. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and Biological Characterization of 3-Substituted-1<i>H</i>-indoles as Ligands of GluN2B-Containing <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptors
  作者：Rosaria Gitto、Laura De Luca、Stefania Ferro、Maria Rosa Buemi、Emilio Russo、Giovambattista De Sarro、Lara Costa、Lucia Ciranna、Orazio Prezzavento、Emanuela Arena、Simone Ronsisvalle、Giuseppe Bruno、Alba Chimirri

  DOI：10.1021/jm2008002

  日期：2011.12.22

  As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-l-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [H-3]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the sigma(2) receptor.