3-methyl-4-oxo-6-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester | 27398-61-4

• 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: 3-methyl-4-oxo-6-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: IND126432；3-methyl-4-oxo-6-phenyl-4,5,6,7-tetrahydro-indole-2-carboxylic acid ethyl ester；ethyl 3-methyl-4-oxo-6-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate；ethyl 3-methyl-4-oxo-6-phenyl-1,5,6,7-tetrahydroindole-2-carboxylate
• CAS: 27398-61-4
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: JKCCBJPERVOVSS-UHFFFAOYSA-N

物化性质

• 熔点：
  207-208 °C (decomp)(Solv: benzene (71-43-2))
• 沸点：
  500.1±50.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-4-oxo-6-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester 、 对硝基苯磺酰氯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  A library synthesis of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as anti-tumor agents

  摘要：

  As a result of a hit-to-lead program using a technique of solution-phase parallel synthesis, a highly potent (2,4-dimethoxyphenyl)- [6- (3 -fluorophenyl)-4-hydroxy- 3 -methylbenzofuran -2 -yl] methanone (15b) was synthesized as an optimized derivative of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester (1), which was discovered as a screening hit from small-molecule libraries and exhibited selective cytotoxicity against a tumorigenic cell line. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.067
• 作为产物：
  描述：

  5-phenyl-cyclohexane-1,3-dione 、 乙酰乙酸乙酯 在 溶剂黄146 、 sodium nitrite 、 锌 作用下， 反应 6.5h， 以34%的产率得到3-methyl-4-oxo-6-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  作为有效抗肿瘤剂的3-甲基-4-氧代-6-苯基-4,5,6,7-四氢苯并呋喃-2-羧酸乙酯衍生物的合成和评价。

  摘要：

  为了构建新的组合文库，通过替换通过筛选针对致瘤细胞系的细胞毒剂而发现的命中化合物的核心结构来创建先导化合物。新设计的化合物保持了生物活性，并允许构建抗肿瘤药物的替代文库。

  DOI：

  10.1248/cpb.53.638

文献信息

• [EN] 6-(2-FURYL)-3-METHYL-4-OXO-1,5,6,7-TETRAHYDROINDOLE-2-CARBOXYLATE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS DE 6-(2-FURYL)-3-MÉTHYL-4-OXO-1,5,6,7-TÉTRAHYDROINDOLE-2-CARBOXYLATE ET LEURS UTILISATIONS
  申请人：ISTITUTO EUROP DI ONCOLOGIA S R L

  公开号：WO2011073929A1

  公开（公告）日：2011-06-23

  The present invention relates to 6-(2-furyl)-3-methyl-4-oxo-1,5,6,7-tetrahydroindole-2- carboxylate derivatives, to a process for their preparation, to pharmaceutical compositions containing them and to their use in the treatment of cell proliferative disorders including cancer, preferably multidrug resistant cancer.

  本发明涉及6-(2-呋喃基)-3-甲基-4-氧代-1,5,6,7-四氢吲哚-2-羧酸酯衍生物，以及它们的制备方法、含有它们的药物组合物，以及它们在治疗包括癌症在内的细胞增殖紊乱疾病中的应用，尤其是多药耐药癌症的治疗。
• NOVEL ANTIPRION COMPOUNDS
  申请人：The Regents of the University of California

  公开号：US20140329863A1

  公开（公告）日：2014-11-06

  Described herein are novel compositions and methods of treatment addressing diseases such as neurodegenerative diseases, including prion diseases and Alzheimer's disease.

  本文描述了一种新的组合物和治疗方法，用于治疗神经退行性疾病，包括朊病和阿尔茨海默病。
• ANTIMETASTATIC COMPOUNDS
  申请人：Hansen Marc

  公开号：US20130158035A1

  公开（公告）日：2013-06-20

  Screening methods for identifying compounds and compounds and pharmaceutical compositions for treating and preventing cancer are disclosed. The compounds affect signal transduction downstream of the MET receptor.
• [EN] ANTIMETASTATIC COMPOUNDS<br/>[FR] COMPOSÉS ANTIMÉTASTATIQUES
  申请人：UNIV BRIGHAM YOUNG

  公开号：WO2012027392A2

  公开（公告）日：2012-03-01

  Screening methods for identifying compounds and compounds and pharmaceutical compositions for treating and preventing cancer are disclosed. The compounds affect signal transduction downstream of the MET receptor.
• [EN] NOVEL ANTIPRION COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS D'ANTIPRION
  申请人：UNIV CALIFORNIA

  公开号：WO2013033037A2

  公开（公告）日：2013-03-07

  Described herein are novel compositions and methods of treatment addressing diseases such as neurodegenerative diseases, including prion diseases and Alzheimer's disease.