2,2,2-trifluoro-1-(6-methyl-1H-indol-3-yl)-ethanone | 676476-82-7

• 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: 2,2,2-trifluoro-1-(6-methyl-1H-indol-3-yl)-ethanone
• 英文别名: 1-(6-methyl-1H-indol-3-yl)-2,2,2-trifluoroethanone；2,2,2-trifluoro-1-(6-methyl-1H-indole-3-yl)ethanone；2,2,2-trifluoro-1-(6-methyl-1H-indol-3-yl)ethanone；2,2,2-Trifluoro-1-(6-methyl-3-indolyl)ethanone
• CAS: 676476-82-7
• 化学式: C₁₁H₈F₃NO
• 分子量: 227.186
• InChiKey: FGKOAZGNYHYTKU-UHFFFAOYSA-N

物化性质

• 沸点：
  316.6±37.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(6-methyl-1H-indol-3-yl)-ethanone 在 4-二甲氨基吡啶 、 水 、 溴 、 potassium carbonate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-bromo-6-methyl-indol-1-yl}acetic acid methyl ester
  参考文献：
  名称：

  N-[6-(4-Butanoyl-5-methyl-1H-pyrazol-1-yl)pyridazin-3-yl]-5-chloro-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1H-indole-3-carboxamide (SAR216471), a Novel Intravenous and Oral, Reversible, and Directly Acting P2Y12 Antagonist

  摘要：

  In the search of a potential backup for clopidogrel, we have initiated a HTS campaign designed to identify novel reversible P2Y12 antagonists. Starting from a hit with low micromolar binding activity, we report here the main steps of the optimization process leading to the identification of the preclinical candidate SAR216471. It is a potent, highly selective, and reversible P2Y12 receptor antagonist and by far the most potent inhibitor of ADP-induced platelet aggregation among the P2Y12 antagonists described in the literature. SAR216471 displays potent in vivo antiplatelet and antithrombotic activities and has the potential to differentiate from other antiplatelet agents.

  DOI：

  10.1021/jm500588w
• 作为产物：
  描述：

  6-甲基吲哚 、 三氟乙酸酐 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以to afford 2,2,2-trifluoro-1-(6-methyl-1H-indol-3-yl)-ethanone (146 mg, 8%) as a white solid的产率得到2,2,2-trifluoro-1-(6-methyl-1H-indol-3-yl)-ethanone
  参考文献：
  名称：

  Indole-3-carboxamides as glucokinase activators

  摘要：

  本发明提供了式I的葡萄糖激酶激活剂：其中R1、R2和R3在说明书中定义。葡萄糖激酶激活剂在治疗II型糖尿病中增加胰岛素分泌方面很有用。

  公开号：

  US06881844B2

文献信息

• NOVEL INDOL CARBOXYLIC ACID BISPYRIDYL CARBOXAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD AND COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：SEONG Churlmin

  公开号：US20090258876A1

  公开（公告）日：2009-10-15

  Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT 2c receptors, act selectively on the 5-HT 2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT 2c receptors.

  本公开涉及一种新的吲哚羧酸双吡啶羧酰胺衍生物，其制备方法，以及包含该衍生物作为活性成分的用于预防或治疗肥胖、泌尿系统疾病和中枢神经系统疾病的组合物。根据本发明的吲哚羧酸双吡啶羧酰胺衍生物具有高亲和力5-HT2c受体，对5-HT2c受体选择性作用，这些衍生物很少出现由其他受体引起的不良反应。由于这些衍生物有效抑制5-羟色胺活性，它们可能对治疗或预防肥胖；泌尿系统疾病，如尿失禁、早泄、勃起功能障碍和前列腺增生；以及与5-HT2c受体相关的中枢神经系统疾病，如抑郁症、焦虑症、关注症、恐慌症、癫痫、强迫症、偏头痛、睡眠障碍、戒毒、阿尔茨海默病和精神分裂症可能有用。
• Indole-3-carboxamides as glucokinase activators
  申请人：——

  公开号：US20040067939A1

  公开（公告）日：2004-04-08

  The present invention provides glucokinase activators of formula I: 1 wherein R 1 , R 2 and R 3 are defined in the specification. Glucokinase activators are useful for increasing insulin secretion in the treatment of type II diabetes.

  本发明提供了一种化学式为I:1的葡萄糖激酶激活剂，其中R1、R2和R3在说明书中有定义。葡萄糖激酶激活剂在治疗II型糖尿病中有增加胰岛素分泌的作用。
• Novel indol carboxylic acid bispyridyl carboxamide derivatives as 5-HT2c receptor antagonists
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：EP2108649B1

  公开（公告）日：2013-04-24
• [EN] NOVEL INDOL CARBOXYLIC ACID BISPYRIDYL CARBOXAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD AND COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT<br/>[FR] NOUVEAUX DÉRIVÉS DE BISPYRIDYL CARBOXAMIDE D'ACIDE INDOLE CARBOXYLIQUE, LEURS SELS PHARMACEUTIQUEMENT ACCEPTABLES, PROCÉDÉ DE PRÉPARATION ET COMPOSITION LES CONTENANT EN TANT D'INGRÉDIENT ACTIF
  申请人：KOREA RESERACH INST OF CHEMICA

  公开号：WO2009125923A3

  公开（公告）日：2009-12-03
• Synthesis and structure–activity relationship of 1H-indole-3-carboxylic acid pyridine-3-ylamides: A novel series of 5-HT2C receptor antagonists
  作者：Chul Min Park、So Young Kim、Woo Kyu Park、No Sang Park、Churl Min Seong

  DOI：10.1016/j.bmcl.2008.06.064

  日期：2008.7

  A novel series of 1H-indole-3-carboxylic acid pyridine-3-ylamides were synthesized and identified to show high affinity and selectivity for 5-HT2C receptor. Among them, 1H-indole-3-carboxylic acid[6-(2chloro-pyridin-3-yloxy)-pyridin-3-yl]-amide (15k) exhibits the highest affinity (IC50 = 0.5 nM) with an excellent selectivity (>2000 times) over other serotonin (5-HT1A, 5-HT2A, and 5-HT6) and dopamine (D-2-D-4) receptors. (C) 2008 Elsevier Ltd. All rights reserved.