(1-methyl-1H-indol-3-yl)(1H-pyrrol-3-yl)methanone | 220968-62-7

• 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-1H-indol-3-yl)(1H-pyrrol-3-yl)methanone
• 英文别名: (1-methylindol-3-yl)-(1H-pyrrol-3-yl)methanone
• CAS: 220968-62-7
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: CPGDZUGIBQACKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1-methyl-1H-indol-3-yl)(1H-pyrrol-3-yl)methanone 在 tris[2-(methoxyethoxy)ethyl]amine 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 1.0h， 生成 [3-(1-Methyl-1H-indole-3-carbonyl)-pyrrol-1-yl]-acetic acid
  参考文献：
  名称：

  Substituted Pyrrol-1-ylacetic Acids That Combine Aldose Reductase Enzyme Inhibitory Activity and Ability To Prevent the Nonenzymatic Irreversible Modification of Proteins from Monosaccharides

  摘要：

  Starting from the known inhibitory activity of (3-benzoylpyrrol-1-yl)acetic acid (1) and (2-benzoylpyrrol-1-yl)acetic acid (II), a series of 3-aroyl and 2,4-bis-aroyl derivatives (54-75) were synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. It was found that a number of the tested compounds exhibited considerable activity in the micromolar range. Important structural features for the potent compounds is the presence of substituents with relatively low Hammett sigma values and/ or moieties which increase their overall aromatic area. The most active derivative was the [2,4-bis(4-methoxybenzoyl)pyrrol-1-yl] acetic acid (75), with potency favorably compared to known ARIs such as tolrestat, epalrestat, zopolrestat, and fidarestat. Four selected derivatives were also evaluated for their ability to interfere with the oxidative modification of serum albumin in an in vitro experimental glycation model of diabetes mellitus. All of them showed considerable activity, comparable to the known inhibitor trolox. Our results, taken together, indicate that compound 75 combines favorably two biological activities directly connected to a number of pathological conditions related to the chronic diabetes mellitus.

  DOI：

  10.1021/jm0209477
• 作为产物：
  描述：

  1-甲基-1H-吲哚-3-羰酰氯 在 三氯化铝 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 (1-methyl-1H-indol-3-yl)(1H-pyrrol-3-yl)methanone
  参考文献：
  名称：

  1-苯磺酰基-1 H-吡咯的Friedel-crafts酰化制备3-芳酰基吡咯的研究

  摘要：

  在这项工作中，我们研究了氯化铝催化的1-苯磺酰基-1 H-吡咯与一系列11种芳酰氯的反应。形成的产物不是分离的，而是水解成目标3-芳基吡咯的总产率，通常高于50％。但是，在富含π电子的1-苯基-1 H-吡咯-3-羰基氯和1-甲基-1 H-吲哚-3-羰基氯的情况下，发生了显着的C-2取代，导致分离出相应的1-苯磺酰基-2-芳酰基吡咯作为主要或唯一产品。从1-三异丙基硅烷基-1 H-吡咯开始合成所需的C-3异构体。

  DOI：

  10.1002/jhet.5570350619

文献信息

• Substituted Pyrrol-1-ylacetic Acids That Combine Aldose Reductase Enzyme Inhibitory Activity and Ability To Prevent the Nonenzymatic Irreversible Modification of Proteins from Monosaccharides
  作者：Ioannis Nicolaou、Vassilis J. Demopoulos

  DOI：10.1021/jm0209477

  日期：2003.1.1

  Starting from the known inhibitory activity of (3-benzoylpyrrol-1-yl)acetic acid (1) and (2-benzoylpyrrol-1-yl)acetic acid (II), a series of 3-aroyl and 2,4-bis-aroyl derivatives (54-75) were synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. It was found that a number of the tested compounds exhibited considerable activity in the micromolar range. Important structural features for the potent compounds is the presence of substituents with relatively low Hammett sigma values and/ or moieties which increase their overall aromatic area. The most active derivative was the [2,4-bis(4-methoxybenzoyl)pyrrol-1-yl] acetic acid (75), with potency favorably compared to known ARIs such as tolrestat, epalrestat, zopolrestat, and fidarestat. Four selected derivatives were also evaluated for their ability to interfere with the oxidative modification of serum albumin in an in vitro experimental glycation model of diabetes mellitus. All of them showed considerable activity, comparable to the known inhibitor trolox. Our results, taken together, indicate that compound 75 combines favorably two biological activities directly connected to a number of pathological conditions related to the chronic diabetes mellitus.
• A study of the friedel-crafts acylation of 1-benzenesulfonyl-1<i>H</i>-pyrrole in the preparation of 3-aroylpyrroles
  作者：Ioannis Nicolaou、Vassilis J. Demopoulos

  DOI：10.1002/jhet.5570350619

  日期：1998.11

  In this work, we studied the aluminum chloride catalyzed reaction of 1-benzenesulfonyl-1H-pyrrole with a series of eleven aroyl chlorides. The products formed were not isolated, but hydrolyzed to the target 3-aroylpyrroles in overall yields, usually, higher than 50%. However, in the cases with the π electron rich 1-phenyl-1H-pyrrole-3-carbonyl chloride and 1-methyl-1H-indole-3-carbonyl chloride significant

  在这项工作中，我们研究了氯化铝催化的1-苯磺酰基-1 H-吡咯与一系列11种芳酰氯的反应。形成的产物不是分离的，而是水解成目标3-芳基吡咯的总产率，通常高于50％。但是，在富含π电子的1-苯基-1 H-吡咯-3-羰基氯和1-甲基-1 H-吲哚-3-羰基氯的情况下，发生了显着的C-2取代，导致分离出相应的1-苯磺酰基-2-芳酰基吡咯作为主要或唯一产品。从1-三异丙基硅烷基-1 H-吡咯开始合成所需的C-3异构体。