5-[(3-aminocarbonyl)benzyl]-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid

• 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-[(3-aminocarbonyl)benzyl]-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid
• 英文别名: 5-(3-Carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid；5-[(3-carbamoylphenyl)methyl]-7,8,9,10-tetrahydro-6H-cyclohepta[b]indole-4-carboxylic acid
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: GKBQRPKZHUFGOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 5-(3-cyanobenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-[(3-aminocarbonyl)benzyl]-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid
  参考文献：
  名称：

  N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte fatty-acid binding protein (A-FABP) inhibitors

  摘要：

  Small molecule inhibitors of adipocyte fatty-acid binding protein (A-FABP) have gained renewed interest following the recent publication of pharmacologically beneficial effects of such inhibitors. Despite the potential utility of selective A-FABP inhibitors within the fields of metabolic disease, inflammation and atherosclerosis, there are few examples of useful A-FABP inhibitors in the public domain. Herein, we describe the optimization of N-benzyl-tetrahydrocarbazole derivatives through the use of co-crystal structure guided medicinal chemistry efforts. This led to the identification of a potent and selective class of A-FABP inhibitors as illustrated by N-benzyl-hexahydrocyclohepta[b]indole 30.

  DOI：

  10.1016/j.bmcl.2009.01.084

文献信息

• [EN] NOVEL INDOLE DERIVATES AS FABP-4 INHIBITORS<br/>[FR] NOUVEAUX DERIVES D'INDOLE UTILES COMME INHIBITEURS DE FABP-4
  申请人：BIOVITRUM AB

  公开号：WO2004063156A1

  公开（公告）日：2004-07-29

  The present invention relates to novel compounds (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, A, B, n, X, and Y are as defined in the description and claims; and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament, which acts on the fatty acid binding protein FABP-4. The present invention relates to novel compounds (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, A, B, n, X, and Y are as defined in the description and claims; and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament, which acts on the fatty acid binding protein FABP-4.

  本发明涉及新化合物（I），其中R0、R1、R2、R3、R4、R5、R6、R7、R8、A、B、n、X和Y如描述和权利要求中所定义；以及包含这些化合物的药物组合物，以及这些化合物在医学中的使用和用于制备作用于脂肪酸结合蛋白FABP-4的药物的方法。
• [EN] ANTIVIRAL USE OF FABP4 MODULATING COMPOUNDS<br/>[FR] UTILISATION ANTIVIRALE DE COMPOSÉS MODULANT LA FABP4
  申请人：CRESCENTA BIOSCIENCES

  公开号：WO2022010951A1

  公开（公告）日：2022-01-13

  A method for treating a viral disease in a subject comprising administering to said subject a therapeutically effective dose of one or more compounds that bind to fatty acid binding protein FABP4, with compounds described in the specification some having the general formula, Formula I-Formula XII, where W1 – W4 Z1-Z4 Z1 – Z5 X, Y, n, and R1 – R8 are as defined in the claims and description of embodiments. In examples, the ring Z contains Z1-Z4. In other examples, the ring Z contains Z1-Z5. (I)

  一种治疗受试者病毒性疾病的方法，包括向该受试者投予治疗有效剂量的一个或多个结合到脂肪酸结合蛋白FABP4的化合物，其中所述化合物在说明书中被描述，其中一些具有一般式I-式XII，其中W1-W4，Z1-Z4，Z1-Z5，X，Y，n和R1-R8如权利要求和实施例的描述中所定义。在示例中，环Z包含Z1-Z4。在其他示例中，环Z包含Z1-Z5。（I）
• CYCLOALKANYL[B]INDOLES USEFUL AS GLP-1 MODULATORS
  申请人：Trustees of Dartmouth College

  公开号：EP2887804B1

  公开（公告）日：2021-01-27
• COMPOSITIONS AND METHODS FOR TREATING AND/OR PREVENTING CANCER BY INHIBITING FATTY ACID BINDING PROTEINS
  申请人：Lengyel Ernst

  公开号：US20120289570A1

  公开（公告）日：2012-11-15

  The present invention concerns methods and compositions for the inhibition or reduction of the primary tumor and metastasis by inhibition of fatty acid binding proteins.
• Compositions and Methods for Treating and/or Preventing Cancer by Inhibiting Fatty Acid Binding Proteins
  申请人：The University of Chicago

  公开号：US20140363522A1

  公开（公告）日：2014-12-11

  The present invention concerns methods and compositions for the inhibition or reduction of the primary tumor and metastasis by inhibition of fatty acid binding proteins.