1-(2-oxopropyl)indole-2,3-dione | 70097-14-2

• 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: 1-(2-oxopropyl)indole-2,3-dione
• 英文别名: N-acetonyl-isatin；N-acetonylisatin；1H-Indole-2,3-dione, 1-(2-oxopropyl)-
• CAS: 70097-14-2
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: WVUROUHQGKHFNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-oxopropyl)indole-2,3-dione 在 sodium hydroxide 、 N,N-二甲基甲酰胺 作用下， 反应 1.5h， 生成 2-acetyl-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Syntheses of 1-alkyl-2-acylindoles, 1-alkyl-2-acylindole-3-carboxylic acids, and their esters, in superbasic media

  摘要：

  DOI：

  10.1007/bf01165901
• 作为产物：
  描述：

  靛红 、 1-碘丙烷-2-酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以40%的产率得到1-(2-oxopropyl)indole-2,3-dione
  参考文献：
  名称：

  卤代甲基酮直接将Isatin进行N烷基化

  摘要：

  DOI：

  10.1007/s10593-005-0289-y

文献信息

• A simple synthesis of 2-acyl indoles from isatins
  作者：David St. C. Black、Laurence C. H. Wong

  DOI：10.1039/c39800000200

  日期：——

  N-Phenacyl- and N-acetonyl-isatins can be prepared and converted by treatment with sodium hydroxide into 2-acyl indoles and/or 2-acyl indole-3-carboxylic acids.

  Ñ -Phenacyl-和Ñ -acetonyl-靛红可制备并通过用氢氧化钠处理转化成2-酰基吲哚和/或2-酰基吲哚-3-羧酸。
• N-Heterocyclic carbene catalyzed desymmetrization of diols: access to enantioenriched oxindoles having a C3-quaternary stereocenter
  作者：Sourav Dutta、Arka Porey、Joyram Guin

  DOI：10.1039/d3cc00489a

  日期：——

  Herein, we describe an effective strategy for enantioselective synthesis of oxindoles having a C3-quaternary stereocenter via N-heterocyclic carbene (NHC) catalyzed desymmetrization of diols. The process is based on the catalytic asymmetric transfer acylation of primary alcohols using readily available aldehydes as an acylation agent. The reaction enables easy access to diversely functionalized C3-quaternary

  在此，我们描述了一种通过N-杂环卡宾 (NHC) 催化的二醇去对称化对映选择性合成具有 C3-季立体中心的羟吲哚的有效策略。该过程基于伯醇的催化不对称转移酰化，使用容易获得的醛作为酰化剂。该反应可以轻松获得具有出色对映选择性的多种功能化的 C3-季羟吲哚。通过制备 (−)-esermethole 和 (−)-physostigmine 的关键中间体，进一步证明了该过程的合成潜力。
• Synthesis of 2-acylindoles from ?-(N-isatinyl) ketones
  作者：V. I. Gorgos、L. M. Zorin、G. I. Zhungietu、M. A. Rekhter

  DOI：10.1007/bf00515352

  日期：1983.11
• Therapeutic investigations of novel indoxyl-based indolines: A drug target validation and Structure-Activity Relationship of angiotensin-converting enzyme inhibitors with cardiovascular regulation and thrombolytic potential
  作者：A. Manikandan、Pearl Moharil、M. Sathishkumar、C. Muñoz-Garay、A. Sivakumar

  DOI：10.1016/j.ejmech.2017.09.076

  日期：2017.12

  A family of 12 members of Naphthalene-2-ol-indolin-2-one-thiocarbamides (5a-1) with pharmacological potentials of cardiovascular modulator were efficiently synthesized and evaluated. These compounds show inhibitory activity on angiotensin-converting enzyme (ACE), which is a principal constituent of the renin angiotensin system and causative source for hypertension (HTN) (elevated blood pressure) and congestive heart failure (CHF), a parameter that was tested in this report. Prior to this, to get more insight into the binding mode and inhibition of human ACE C-domain (PDB ID: 2XY9) and N-domain (PDB ID: 3NXQ) compounds 5a-1 was docked into the active site of them. The established inhibitory constant (Ki) (range 40-500 nM) and least binding affinities (-18.52 to 30.57 kcal/mol) indicated the therapeutic selectivity of compounds 5a-1 towards ACE C-domain inhibition over ACE N-domain. The cytotoxicity effect of most potent compounds among 5a-1 were tested in normal breast cells and MCF-7 cell lines. Simultaneously, H2O2 induced antioxidant and DNA damage assessment was executed. Eventually, a thrombolytic activity followed by a human red blood cell (HRBC) membrane stabilization study to ensure the relaxation of blood and stabilization of RBC was executed. Structure-Activity Relationship (SAR) study discloses the potential of 5c, 5h, and 5k as cardiovascular protective therapeutic agents among 5a-1. (C) 2017 Elsevier Masson SAS. All rights reserved.
• BLACK D. S. C.; WONG L. C. H., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 4, 200
  作者：BLACK D. S. C.、 WONG L. C. H.

  DOI：——

  日期：——