2-(7-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid | 1206125-25-8

• 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-(7-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
• 英文别名: 2-(7-methoxy-1H,2H,3H,4H-cyclopenta[b]indol-3-yl)acetic acid；1,2,3,4-Tetrahydro-7-methoxycyclopent[b]indole-3-acetic acid
• CAS: 1206125-25-8
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: FRFBAYPUBMZCKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(7-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 乙醇 、 水 为溶剂， 以98%的产率得到2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
  参考文献：
  名称：

  A novel Fischer pseudo-benzylic decarboxylation approach to the 1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl system

  摘要：

  A novel Fischer pseudo-benzylic decarboxylation approach to the 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl system was developed starting from geminally substituted cyclopentanone derivatives and appropriately substituted phenyl hydrazines. In addition, we demonstrate that substituents at the 3- and 7-positions can, for example, be useful synthetic handles for further functionalization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.101
• 作为产物：
  描述：

  3-(carboxymethyl)-7-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indole-3-carboxylic acid 在 溶剂黄146 作用下， 反应 4.5h， 以78%的产率得到2-(7-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
  参考文献：
  名称：

  [EN] SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS
  [FR] DÉRIVÉS DE L'ACIDE 1,2,3,4-TÉTRAHYDROCYCLOPENTA[B]INDOL-3-YLE ACÉTIQUE SUBSTITUÉ UTILISÉS DANS LE TRAITEMENT DES MALADIES AUTO-IMMUNES ET INFLAMMATOIRES

  摘要：

  本发明涉及某些替代的1,2,3,4-四氢环戊基吲哚-3-基乙酸衍生物的化合物（Ia）及其药用盐，这些化合物展示出有用的药理特性，例如作为S1P1受体的激动剂。本发明还提供了含有该发明化合物的药物组合物，以及使用该发明化合物和组合物治疗S1P1受体相关疾病的方法，例如银屑病、类风湿关节炎、克罗恩病、移植排斥、多发性硬化症、系统性红斑狼疮、溃疡性结肠炎、I型糖尿病、痤疮、微生物感染或疾病以及病毒感染或疾病。

  公开号：

  WO2010011316A1

文献信息

• SUBSTITUTED 1,2,3,4-TETRAHYDROCYCLOPENTA[B]INDOL-3-YL)ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS
  申请人：Jones Robert M.

  公开号：US20110130409A1

  公开（公告）日：2011-06-02

  The present invention relates to certain substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives of Formula (Ia) and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists of the S1P1 receptor. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of S1P1 receptor-associated disorders, for example, psoriasis, rheumatoid arthritis, Crohn's disease, transplant rejection, multiple sclerosis, systemic lupus erythematosus, ulcerative colitis, type I diabetes, acne, microbial infections or diseases and viral infections or diseases.

  本发明涉及某些取代的1,2,3,4-四氢环戊[b]吲哚-3-基乙酸衍生物（Ia式）及其药学上可接受的盐，其具有有用的药理特性，例如作为S1P1受体激动剂。本发明还提供了含有该发明化合物的药物组合物，以及使用该化合物和组合物治疗S1P1受体相关疾病的方法，例如牛皮癣、类风湿性关节炎、克隆病、移植排斥、多发性硬化症、系统性红斑狼疮、溃疡性结肠炎、1型糖尿病、痤疮、微生物感染或疾病和病毒感染或疾病。
• SUBSTITUTED 1,2,3,4-TETRAHYDROCYCLOPENTA[b]INDOL-3-YL)ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS
  申请人：Arena Pharmaceuticals, Inc.

  公开号：US20140038987A1

  公开（公告）日：2014-02-06

  The present invention relates to certain substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives of Formula (Ia) and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists of the S1P1 receptor. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of S1P1 receptor-associated disorders, for example, psoriasis, rheumatoid arthritis, Crohn's disease, transplant rejection, multiple sclerosis, systemic lupus erythematosus, ulcerative colitis, type I diabetes, acne, microbial infections or diseases and viral infections or diseases.

  本发明涉及某些取代的1,2,3,4-四氢环戊[b]吲哚-3-基)乙酸衍生物(Ia式)及其药学上可接受的盐，这些衍生物具有有用的药理学特性，例如作为S1P1受体的激动剂。本发明还提供了含有本发明化合物的药物组合物，并且提供了使用本发明化合物和组合物治疗S1P1受体相关疾病的方法，例如牛皮癣、类风湿性关节炎、克罗恩病、移植排斥、多发性硬化症、全身性红斑狼疮、溃疡性结肠炎、1型糖尿病、痤疮、微生物感染或疾病和病毒感染或疾病。
• 一种四氢环戊二烯并[b]吲哚-3-基乙酸及其衍生物单一对映异构体的制备方法
  申请人：安徽艾立德制药有限公司

  公开号：CN117430547A

  公开（公告）日：2024-01-23

  本发明提供一种四氢环戊二烯并[b]吲哚‑3‑基乙酸及其衍生物单一对映异构体的制备方法以及制备依曲莫德过程中的关键中间体。具体是以手性胺为拆分剂，将四氢环戊二烯并[b]吲哚‑3‑基乙酸消旋体和拆分剂在溶剂中反应生成对映异构体盐，利用在第一对映异构体盐在第二对映异构体盐的浓度接近其饱和点或低于其饱和点的温度下能够分离出来的特点，通过盐重结晶、游离、萃取、蒸馏等工艺分离出ee值在98%以上的单一对映异构体酸，接着酯化反应制备衍生物。本发明制备方法的拆分效率高、操作简单、工艺流程短、成本低、选择性高，适合工业化生产。
• SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS
  申请人：Arena Pharmaceuticals, Inc.

  公开号：EP2326621A1

  公开（公告）日：2011-06-01
• SUBSTITUTED (1,2,3,4-TETRAHYDROCYCLOPENTA[b]INDOL-3-YL)ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS
  申请人：Arena Pharmaceuticals, Inc.

  公开号：US20190135752A1

  公开（公告）日：2019-05-09

  The present invention relates to certain substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives of Formula (Ia) and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists of the S1P1 receptor. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of S1P1 receptor-associated disorders, for example, psoriasis, rheumatoid arthritis, Crohn's disease, transplant rejection, multiple sclerosis, systemic lupus erythematosus, ulcerative colitis, type I diabetes, acne, microbial infections or diseases and viral infections or diseases.