5-chloro-7-nitro-1H-indole-2-carboxylic acid ethyl ester | 91119-27-6

• 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: 5-chloro-7-nitro-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 5-chloro-7-nitroindole-2-carboxylate；ethyl 5-chloro-7-nitro-1H-indole-2-carboxylate
• CAS: 91119-27-6
• 化学式: C₁₁H₉ClN₂O₄
• 分子量: 268.656
• InChiKey: GTZXEFZOOWYOJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-7-nitro-1H-indole-2-carboxylic acid ethyl ester 在 N,N-二甲基甲酰胺 草酰氯 、 硫酸 、 氨 、 乙酸酐 、 铁粉 、 氯化铵 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 18.0h， 生成 (S)-5-chloro-7-((4-fluorobenzyl)amino)-3-((2-(phenoxymethyl)morpholino)sulfonyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  [EN] A PROCESS FOR THE PREPARATION OF MORPHOLINO SULFONYL INDOLE DERIVATIVES
  [FR] PROCÉDÉ POUR LA PRÉPARATION DE DÉRIVÉS DE MORPHOLINOSULFONYLINDOLE

  摘要：

  本发明涉及一种制备式(I)化合物的方法，这些化合物是吗啡啶磺酰基吲哚衍生物。式(I)化合物能够抑制、调节或调控胰岛素样生长因子I受体或胰岛素受体。本发明还涉及制备式(I)化合物的药用可接受盐的方法。

  公开号：

  WO2012143874A1
• 作为产物：
  描述：

  2-nitro-4-chlorophenylhydrazine 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.08h， 生成 5-chloro-7-nitro-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Detailed structure–activity relationship of indolecarboxamides as H4 receptor ligands

  摘要：

  A series of 76 derivatives of the indolecarboxamide 1 were synthesized, which allows a detailed SAR investigation of this well known scaffold. The data enable the definition of a predictive QSAR model which identifies several compounds with an activity comparable to 1. A selection of these new H4R antagonists was synthesized and a comparison of predicted and measured values demonstrates the robustness of the model (47-55). In addition to the H-4-receptor activity general CMC and DMPK properties were investigated. Some of the new analogs are not only excellently soluble, but display a significantly increased half-life in mouse liver microsomes as well. These properties qualify these compounds as a possible new standard for future in vivo studies (e.g 51, 52 and 55). Moreover, the current studies also provide valuable information on the potential receptor ligand interactions between the indolcarboxamides and the H4R protein. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.016

文献信息

• PROCESS FOR THE PREPARATION OF MORPHOLINO SULFONYL INDOLE DERIVATIVES
  申请人：Mascarenhas Malcolm

  公开号：US20140046059A1

  公开（公告）日：2014-02-13

  The present invention relates to a process for the preparation of the compounds of formula (I) which are morpholino sulphonyl indole derivatives. The compounds of formula (I) are capable of inhibiting, modulating or regulating Insulin-Like-Growth Factor I Receptors or Insulin Receptors. The present invention also relates to the processes for preparation of the pharmaceutically acceptable salts of the compounds of formula (I).

  本发明涉及一种制备公式（I）化合物的方法，该化合物是吗啡啶磺酰基吲哚衍生物。公式（I）化合物能够抑制、调节或调节胰岛素样生长因子I受体或胰岛素受体。本发明还涉及制备公式（I）化合物的药物可接受的盐的方法。
• Insulin-Like Growth Factor-1 Receptor Inhibitors
  申请人：Balachandran Sarala

  公开号：US20140045832A1

  公开（公告）日：2014-02-13

  The present invention relates to compounds that are capable of inhibiting, modulating and/or regulating Insulin-Like-Growth Factor I Receptor and Insulin Receptor. The compounds of the instant invention possess a core structure that comprises a sulfonyl indole moiety. The present invention is also related to the pharmaceutically acceptable salts, hydrates and stereoisomers of these compounds.

  本发明涉及一种能够抑制、调节和/或调节胰岛素样生长因子I受体和胰岛素受体的化合物。本发明的化合物具有包含磺酰基吲哚基团的核心结构。本发明还涉及这些化合物的药学上可接受的盐、水合物和立体异构体。
• Katti, H. A.; Siddappa, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 12, p. 1205 - 1208
  作者：Katti, H. A.、Siddappa, S.

  DOI：——

  日期：——
• KATTI, H. A.;SIDDAPPA, S., INDIAN J. CHEM., 1983, 22, N 12, 1205-1208
  作者：KATTI, H. A.、SIDDAPPA, S.

  DOI：——

  日期：——
• INSULIN-LIKE GROWTH FACTOR-1 RECEPTOR INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2699567A1

  公开（公告）日：2014-02-26