ethyl 2-(1H-Indol-1-yl)propanoate | 77992-71-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(1H-Indol-1-yl)propanoate
• 英文别名: ethyl 2-indol-1-ylpropanoate
• CAS: 77992-71-3
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: FYCWDFQQAZYIFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1H-Indol-1-yl)propanoate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以81%的产率得到2-(1H-吲哚-1-基)丙酸
  参考文献：
  名称：

  外消旋 2-(1H-Pyrrol-1-yl) 链烷酸作为 α-氨基酸等价物的非酶促、对映收敛动态动力学拆分 (DKR)

  摘要：

  我们报告了一种有效的外消旋 2-(1H-pyrrol-1-yl) 链烷酸动态动力学拆分 (DKR) 系统，该系统由通过活化底物和对映体的快速外消旋化步骤组成。

  DOI：

  10.1246/cl.150826
• 作为产物：
  描述：

  (R,S)-2-(2-phenylsulfonylindol-1-yl)propionic acid ethyl ester 在 Raney nickel 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以74%的产率得到ethyl 2-(1H-Indol-1-yl)propanoate
  参考文献：
  名称：

  2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions

  摘要：

  The N-alkylation of 2- and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions.

  DOI：

  10.1007/s10593-010-0504-3

文献信息

• Photochemical Asymmetric Nickel‐Catalyzed Acyl Cross‐Coupling
  作者：Eugenio Gandolfo、Xinjun Tang、Sudipta Raha Roy、Paolo Melchiorre

  DOI：10.1002/anie.201910168

  日期：2019.11.18

  Photochemical enantioselective nickel-catalyzed cross-coupling reactions are difficult to implement. We report a visible-light-mediated strategy that successfully couples symmetrical anhydrides and 4-alkyl dihydropyridines (DHPs) to afford enantioenriched α-substituted ketones under mild conditions. The chemistry does not require exogenous photocatalysts. It is triggered by the direct excitation of

  光化学对映选择性镍催化的交叉偶联反应难以实现。我们报告了一种可见光介导的策略，该策略成功地将对称酸酐和4-烷基二氢吡啶（DHPs）偶联，以在温和条件下提供对映体富集的α-取代的酮。化学过程不需要外源光催化剂。它是由DHPs的直接激发触发的，DHPs作为自由基源和还原剂，促进了手性催化镍络合物的周转。
• Antifungal and/or antiparasitic pharmaceutical composition and novel indole derivatives as active principle of such a composition
  申请人：——

  公开号：US20040067998A1

  公开（公告）日：2004-04-08

  The present invention relates to novel indole derivatives, their method of preparation and their pharmacological activity as antimycotic and/or antiparasitic compounds.

  这项发明涉及新型吲哚衍生物，它们的制备方法以及它们作为抗真菌和/或抗寄生虫化合物的药理活性。
• An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer
  作者：Helen E. Colley、Munitta Muthana、Sarah J. Danson、Lucinda V. Jackson、Matthew L. Brett、Joanne Harrison、Sean F. Coole、Daniel P. Mason、Luke R. Jennings、Melanie Wong、Vamshi Tulasi、Dennis Norman、Peter M. Lockey、Lynne Williams、Alexander G. Dossetter、Edward J. Griffen、Mark J. Thompson

  DOI：10.1021/acs.jmedchem.5b01312

  日期：2015.12.10

  A number of indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors, although none has yet been successfully developed clinically. We report here a new series of related compounds, modified according to a strategy of reducing aromatic ring count and introducing a greater degree of saturation, which retain potent tubulin polymerization activity but with a distinct SAR from previously documented libraries. A subset of active compounds from the reported series is shown to interact with tubulin at the colchicine binding site, disrupt the cellular microtubule network, and exert a cytotoxic effect against multiple cancer cell lines. Two compounds demonstrated significant tumor growth inhibition in a mouse xenograft model of head and neck cancer, a type of the disease which often proves resistant to chemotherapy, supporting further development of the current series as potential new therapeutics.
• tert-Butyl (2S)-(p-tolylsulfonyloxy)propionate — a suitable reagent for the direct alkylation of indole derivatives
  作者：A. V. Kurkin、D. S. Belov、M. A. Yurovskaya

  DOI：10.1007/s10593-008-0160-z

  日期：2008.9

  A new method is proposed for the synthesis of indole derivatives containing a chiral substituent at the nitrogen atom, which includes the direct alkylation of indole derivatives with tert-butyl (2S)-(p-tolylsulfonyloxy)propionate, obtained from commercial ethyl (S)-lactate with subsequent conversion to the corresponding p-toluenesulfonyloxy derivative by hydrolysis, and esterification.
• Acylated indole derivatives, processes for their preparation and pharmaceutical compositions and drugs comprising them
  申请人：TEIJIN LIMITED

  公开号：EP0022634B1

  公开（公告）日：1983-04-06