1-methyl-1,4,5,6-tetrahydro-7H-indol-7-one | 113342-39-5

• 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-methyl-1,4,5,6-tetrahydro-7H-indol-7-one
• 英文别名: 1-methyl-7-oxo-4,5,6,7-tetrahydroindole；1-Methyl-1,4,5,6-tetrahydro-7H-indole-7-one；1-methyl-4,5,6,7-tetrahydro-1H-indole-7-one；1-methyl-5,6-dihydro-4H-indol-7-one
• CAS: 113342-39-5
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: PRHGWZFYDVSVJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-1,4,5,6-tetrahydro-7H-indol-7-one 在 TEA 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 dimethyl 2-{[(1-methyl-4,5,6,7-tetrahydro-1H-(E)-7-indolyliden)amino]oxy}-(Z)-2-butenedioate
  参考文献：
  名称：

  Pinna, Gerard Aime; Sechi, Mario; Paglietti, Giuseppe, Journal of Chemical Research, Miniprint, 2003, # 3, p. 362 - 380

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(Phenylsulfonyl)-7-oxo-4,5,6,7-tetrahydroindole 在 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 生成 1-methyl-1,4,5,6-tetrahydro-7H-indol-7-one
  参考文献：
  名称：

  PHOTOCHEMOTHERAPEUTIC HETEROCYCLIC AGENTS HAVING ANTIPROLIFERATIVE AND ANTINEOPLASTIC ACTIVITY

  摘要：

  本发明涉及合成新的天使光素类似物，吡咯并[3,2-h]喹啉，用于治疗具有增殖性特征的病理，包括具有肿瘤性质的病理。治疗基于吡咯并[3,2-h]喹啉和紫外线-A光的联合作用，通过被定义为PUVA（苯酞-UVA光）的临床方法。这些化合物最重要的特点是它们在没有任何DNA损伤的情况下发挥显着的光毒性，这是PUVA治疗的副作用的主要来源。

  公开号：

  US20120129884A1

文献信息

• Pyrrolo[3,2-h]quinazolines as Photochemotherapeutic Agents
  作者：Paola Barraja、Libero Caracausi、Patrizia Diana、Alessandra Montalbano、Anna Carbone、Alessia Salvador、Paola Brun、Ignazio Castagliuolo、Silvia Tisi、Francesco Dall'Acqua、Daniela Vedaldi、Girolamo Cirrincione

  DOI：10.1002/cmdc.201100085

  日期：2011.7.4

  with the aim of obtaining new potent photochemotherapeutic agents. Many derivatives caused a significant decrease in cell proliferation in several human tumor cell lines after irradiation with UVA light (GI50=15.2–0.2 μM). Their phototoxicity effected apoptosis in Jurkat cells with the involvement of mitochondria (as determined by the loss of mitochondrial membrane potential and production of reactive

  当归，吡咯并[3,2-的Heteroanalogues ħ ]喹唑啉，与获得新的有效光化学治疗剂的目的进行了合成。许多衍生物引起细胞增殖的显著减少在几种人肿瘤细胞系用UVA光（GI照射后50 = 15.2-0.2μ中号）。它们的光毒性通过线粒体（由线粒体膜电位的丧失和活性氧的产生确定）和溶酶体的作用影响Jurkat细胞的凋亡。这些化合物的光毒性可以通过脂质过氧化来解释。
• Synthesis and Antiproliferative Activity of the Ring System [1,2]Oxazolo[4,5-<i>g</i>]indole
  作者：Paola Barraja、Libero Caracausi、Patrizia Diana、Virginia Spanò、Alessandra Montalbano、Anna Carbone、Barbara Parrino、Girolamo Cirrincione

  DOI：10.1002/cmdc.201200296

  日期：2012.11

  Brand new ring: A series of 27 derivatives of the new ring system [1,2]oxazolo[4,5‐g]indole were conveniently prepared and tested at the NCI for antiproliferative studies. Several of them showed good inhibitory activity toward all tested cell lines, reaching GI50 values generally at the micromolar and sub‐ micromolar levels and in some cases at nanomolar concentrations. The mean GI50 values, calculated

  全新的环：方便地制备了新环系统[1,2]恶唑并[4,5- g ]吲哚的27种衍生物，并在NCI进行了抗增殖研究测试。其中一些对所有测试的细胞系均表现出良好的抑制活性，通常在微摩尔和亚微摩尔水平，在某些情况下在纳摩尔浓度下达到GI 50值。平均GI 50值，全面板上计算，分别在范围0.25-7.08μ中号。
• Synthesis of pyrrolo[3,2-h]quinolinones with good photochemotherapeutic activity and no DNA damage
  作者：Paola Barraja、Libero Caracausi、Patrizia Diana、Anna Carbone、Alessandra Montalbano、Girolamo Cirrincione、Paola Brun、Giorgio Palù、Ignazio Castagliuolo、Francesco Dall’Acqua、Daniela Vedaldi、Alessia Salvador

  DOI：10.1016/j.bmc.2010.04.080

  日期：2010.7

  In the search for new photochemotherapeutic agents, a series of derivatives of the ring system pyrrolo[3,2-h]quinoline—bioisosters of the angular furocoumarin angelicin—were synthesized through a four-step synthetic approach, in reasonable overall yields. Eight of the synthesized derivatives showed a remarkable phototoxicity against a panel of four human tumor cell lines and a great dose UV-A dependence

  在寻找新的光化学治疗剂时，通过四步合成方法以合理的总收率合成了一系列环系统吡咯并[3,2 - h ]喹啉衍生物（角型呋喃香豆素当归的生物异构体）。八种合成衍生物对一组四个人类肿瘤细胞系表现出显着的光毒性，并具有大剂量的UV-A依赖性，在亚微摩尔水平下达到IC 50值。通过一系列的流式细胞仪分析评估了吡咯并[3,2- h ]喹啉光诱导的细胞死亡方式，并进行了其他测试以阐明其作用机理。
• A dichotomy in the Friedel-Crafts reactions of lactones provides a convenient new route to 2-acylated pyrroles and tetrahydroindolones
  作者：David C. Harrowven、Richard F. Dainty

  DOI：10.1016/00404-0399(50)1328-f

  日期：1995.9

  In striking contrast to arenes, N-methylpyrrole undergoes Friedel-Crafts acylation with lactones. The reaction is most efficient with γ- and δ-lactones; ε-lactones proceed with poor overall conversion while β-lactones display poor selectivity. γ-Alkyl-γ-lactones readily yield 4,5,6,7-tetrahydroindol-7-ones through a sequence analogous to the Truce-Olson annulation.

  与芳烃形成鲜明对比的是，N-甲基吡咯与内酯进行了Friedel-Crafts酰化反应。用γ-和δ-内酯进行反应最有效。ε-内酯的总转化率很低，而β-内酯的选择性很差。γ-烷基-γ-内酯通过类似于Truce-Olson环化的序列容易产生4,5,6,7-四氢吲哚-7-。
• Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: a mechanistic interpretation and conversion into 4- and 7-oxoindoles
  作者：Antonio Garrido Montalban、Sven M. Baum、Justin Cowell、Alexander McKillop

  DOI：10.1016/j.tetlet.2012.05.090

  日期：2012.8

  An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7-tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center a to the nitrogen and preparation of enantiomerically enriched products. (c) 2012 Elsevier Ltd. All rights reserved.