2-(7-甲基-1H-吲哚-3-基)-2-氧代乙酰氯 | 59022-69-4

• 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: 2-(7-甲基-1H-吲哚-3-基)-2-氧代乙酰氯
• 英文名称: 2-(7-methyl-1H-indol-3-yl)-2-oxoacetyl chloride
• CAS: 59022-69-4
• 化学式: C₁₁H₈ClNO₂
• 分子量: 221.643
• InChiKey: GKWQILOPRWVNTD-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C (decomp)
• 沸点：
  414.8±37.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(7-甲基-1H-吲哚-3-基)-2-氧代乙酰氯 在 4-二甲氨基吡啶 、 chlorobis(cyclooctene)rhodium(I) dimer 、 (R)-N-cinnamyl-t-butanesulfinamide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 tert-butyl 3-[(1R)-2-ethoxy-1-hydroxy-1-(4-methoxyphenyl)-2-oxoethyl]-7-methylindole-1-carboxylate
  参考文献：
  名称：

  Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters

  摘要：

  第一例催化不对称1,2-加成芳基硼酸到杂芳类α-酮酯的反应已经被开发，用于高效和选择性合成四次碳含量的杂芳类α-羟基酯。在非常温和的条件下，该反应对多种α-酮酯表现良好，包括3-吲哚乙二酸酯、3-苯并呋喃乙二酸酯和3-苯并噻吩乙二酸酯，产物的收率中等到良好，且具有高的对映体过量（高达97%）。

  DOI：

  10.1039/c2ob26316e
• 作为产物：
  描述：

  7-甲基吲哚 、 草酰氯 生成 2-(7-甲基-1H-吲哚-3-基)-2-氧代乙酰氯
  参考文献：
  名称：

  HIV-1附着抑制剂。第2部分：吲哚取代方式的初步调查

  摘要：

  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。

  DOI：

  10.1016/j.bmcl.2009.02.040

文献信息

• Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade
  作者：Long Han、Chuan Liu、Wei Zhang、Xiao-Xin Shi、Shu-Li You

  DOI：10.1039/c3cc47921h

  日期：——

  An enantioselective epoxidation of tryptophols followed by an intramolecular epoxide opening reaction was realized by chiral vanadium catalysts derived from C2 symmetric bis-hydroxamic acid (BHA) ligands. 3a-Hydroxyfuroindoline derivatives with up to 89% yield and 90% ee were obtained under mild reaction conditions.

  通过衍生自C2对称双异羟肟酸（BHA）配体的手性钒催化剂实现了对三酚的对映选择性环氧化，然后进行了分子内环氧化物开环反应。在温和的反应条件下获得了产率高达89％和ee达90％的3a-羟基呋喃二氢吲哚衍生物。
• 3-(7-Azaindolyl)-4-indolylmaleimides as a novel class of mutant isocitrate dehydrogenase-1 inhibitors: Design, synthesis, and biological evaluation
  作者：Yuanyuan Hu、Anhui Gao、Honghui Liao、Mengmeng Zhang、Gaoya Xu、Lixin Gao、Lei Xu、Yubo Zhou、Jianrong Gao、Qing Ye、Jia Li

  DOI：10.1002/ardp.201800039

  日期：2018.10

  A series of 3‐(7‐azainodyl)‐4‐indolylmaleimides was designed, synthesized, and evaluated for their isocitrate dehydrogenase 1 (IDH1)/R132H inhibitory activities. Many compounds such as 11a, 11c, 11e, 11g, and 11s exhibited favorable inhibitory effects on IDH1/R132H and were highly selective against the wild‐type IDH1. Evaluation of the biological activities at the cellular level showed that compounds

  设计、合成了一系列 3-(7-azainodyl)-4-indolylmaleimides，并评估了它们的异柠檬酸脱氢酶 1 (IDH1)/R132H 抑制活性。许多化合物如 11a、11c、11e、11g 和 11s 对 IDH1/R132H 表现出良好的抑制作用，并且对野生型 IDH1 具有高度选择性。在细胞水平上对生物活性的评估表明，化合物 11a、11c、11e、11g 和 11s 可以有效抑制表达 IDH1/R132H 的 U87MG 细胞中 2-羟基戊二酸的产生。基于获得的实验数据讨论了初步构效关系 (SAR) 和分子建模研究。这些发现可能为开发新型 IDH1/R132H 抑制剂提供新的见解。
• 3-Thio-1,2,4-triazoles, novel somatostatin sst2/sst5 agonists
  作者：Marie-Odile Contour-Galcéra、Alban Sidhu、Pascale Plas、Pierre Roubert

  DOI：10.1016/j.bmcl.2005.05.061

  日期：2005.8

  Novel 3-thio-1,2,4-triazoles have been obtained via a solution-phase parallel synthesis strategy, affording potent non-peptidic human somatostatin receptor subtypes 2 and 5 agonists. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of 3-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-4-(indol-3-yl)-maleimides as potent, selective GSK-3β inhibitors and neuroprotective agents
  作者：Qing Ye、Weili Mao、Yubo Zhou、Lei Xu、Qiu Li、Yuanxue Gao、Jing Wang、Chenhui Li、Yazhou Xu、Yuan Xu、Hong Liao、Luyong Zhang、Jianrong Gao、Jia Li、Tao Pang

  DOI：10.1016/j.bmc.2014.12.026

  日期：2015.3

  A series of novel 3-([1,2,4] triazolo[4,3-a] pyridin-3-yl)-4-(indol-3-yl)-maleimides were designed, prepared and evaluated for their GSK-3 beta inhibitory activities. Most compounds showed high potency to GSK-3 beta inhibition with high selectivity. Among them, compounds 7c, 7f, 7h, 7l and 7m significantly reduced GSK-3 beta substrate Tau phosphorylation at Ser396 in primary neurons, showing the inhibition of cellular GSK-3 beta. In the in vitro neuronal injury models, compounds 7c, 7f, 7h, 7l and 7m prevented neuronal death against glutamate, oxygen-glucose deprivation and nutrient serum deprivation which are associated with cerebral ischemic stroke. In the in vivo cerebral ischemia animal model, compound 7f reduced infarct size by 15% and improved the neurological deficit following focal cerebral ischemia. These findings may provide new insights into the development of novel GSK-3b inhibitors with potential neuroprotective activity. (C) 2015 Published by Elsevier Ltd.
• 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.