1,2,3,4-tetrahydrocyclopenta[b]indole-5-carboxylic acid | 422312-00-3

• 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: 1,2,3,4-tetrahydrocyclopenta[b]indole-5-carboxylic acid
• CAS: 422312-00-3
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD09863427
• 分子量: 201.225
• InChiKey: KUCYGAINBAZNHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 1,2,3,4-tetrahydrocyclopenta[b]indole-5-carboxylic acid 在 硫酸 作用下， 生成 Methyl 1,2,3,4-tetrahydrocyclopenta[b]indole-5-carboxylate
  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
• 作为产物：
  描述：

  2-(2-cyclopentylidenehydrazineyl)benzoic acid 在 硫酸 、 溶剂黄146 作用下， 反应 5.0h， 生成 1,2,3,4-tetrahydrocyclopenta[b]indole-5-carboxylic acid
  参考文献：
  名称：

  吲哚二萜的合成研究：（+）-Nodulisporic酸A和B的第二代合成策略的发展。

  摘要：

  公开了基于开发一种新的，有效的模块化吲哚合成的第二代构建（+）-去甲孢子酸A和B的策略，该合成利用顺序Stille交叉偶联/ Buchwald-Hartwig联合/环化策略。由于在我们的第一代方法中的几个高级中间体中观察到的C（24）羟基相当酸不稳定，因此该策略得以发展。

  DOI：

  10.1021/jo062423a

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。
• NOVEL CELL METABOLISM MODULATING COMPOUNDS AND USES THEREOF
  申请人：CRESCENTA BIOSCIENCES

  公开号：US20220002243A1

  公开（公告）日：2022-01-06

  A novel class of compounds according to Formula I, II, or III, wherein W 1 -W 4 , Z 1 -Z 4 , Z 1 -Z 5 , X, Y, n, and R 1 -R 8 are as defined in the claims and description of embodiments that bind to fatty acid binding protein FABP4 and modulate adipocyte metabolism to drive enhanced glucose utilization, as well as pharmaceutical compositions comprising the class of compounds, in combination with a pharmaceutically acceptable diluent or carrier, and optionally, further in combination with a therapeutically active agent, and the use of these compounds in medicine and for the preparation of a medicament in the treatment of disorders acting on the FABP4. In examples, the ring Z contains Z 1 -Z 4 . In other examples, the ring Z contains Z 1 -Z 5 .

  一类化合物，符合公式I、II或III，其中W1-W4、Z1-Z4、Z1-Z5、X、Y、n和R1-R8的定义如权利要求和实施例的描述，这些化合物能够结合脂肪酸结合蛋白FABP4并调节脂肪细胞代谢，以促进葡萄糖利用，以及包含该类化合物的药物组合物，与药学可接受的稀释剂或载体结合，并且可选地与治疗活性剂进一步结合，以及在医学中使用这些化合物，以及用于制备治疗作用于FABP4的疾病的药物。例如，环Z包含Z1-Z4。在其他例子中，环Z包含Z1-Z5。
• Cyclopenta[b][1,4]diazepino[6,7,1-hi]indoles and derivatives
  申请人：Sabb Louise Annmarie

  公开号：US20050004101A1

  公开（公告）日：2005-01-06

  This invention provides compounds of the formulae: wherein: R 1 is hydrogen, —C(O)CH 3 or alkyl of 1-6 carbon atoms; R 2 and R 3 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, cycloalkyl, alkoxy of 1-6 carbon atoms, —CH 2 OH, fluoroalkyl, alkyl sulfonamide of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluoroalkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, aryl, or aroyl; R 4 and R 5 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, halogen, fluoroalkyl, —CN, alkyl sulfonamide of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluoroalkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, or aroyl; R 6 and R 7 are each independently hydrogen, C 1 -C 6 alkyl or cycloalkyl; or a pharmaceutically acceptable salt thereof, as well as pharmaceutical compositions containing these compounds and methods for their use, including treatment of obsessive-compulsive disorder, panic disorder, depression, anxiety, generalized anxiety disorder, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.

  本发明提供了以下式的化合物：其中：R1是氢，—C（O）CH3或1-6碳原子的烷基；R2和R3各自独立地是氢、1-6碳原子的烷基、环烷基、1-6碳原子的烷氧基、—CH2OH、氟代烷基、1-6碳原子的烷基磺酰胺、1-6碳原子的烷基酰胺、氨基、1-6碳原子的烷基氨基、每个烷基基团的1-6碳原子的二烷基氨基、1-6碳原子的氟代烷氧基、2-7碳原子的酰基、芳基或芳酰基；R4和R5各自独立地是氢、1-6碳原子的烷基、1-6碳原子的烷氧基、卤素、氟代烷基、—CN、1-6碳原子的烷基磺酰胺、1-6碳原子的烷基酰胺、氨基、1-6碳原子的烷基氨基、每个烷基基团的1-6碳原子的二烷基氨基、1-6碳原子的氟代烷氧基、2-7碳原子的酰基或芳酰基；R6和R7各自独立地是氢、C1-C6烷基或环烷基；或其药学上可接受的盐，以及含有这些化合物的制药组合物和它们的使用方法，包括治疗强迫症、惊恐障碍、抑郁症、焦虑、广泛性焦虑障碍、精神分裂症、偏头痛、睡眠障碍、进食障碍、肥胖症、癫痫和脊髓损伤。
• PROCESS FOR PREPARATION OF CYCLOPENTA [B] [1,4] DIAZEPINO [6,7,1-HI] INDOLE DERIVATIVES
  申请人：American Home Products Corporation

  公开号：US20020055630A1

  公开（公告）日：2002-05-09

  The present invention provides processes for the preparation of 1, 2, 3, 4, 8, 9, 10, 10 a -octahydro-7bH-cyclopenta[b][1, 4]diazepino[6, 7, 1-hi]indole derivatives of the general formula: 1 wherein: R is H, alkyl, acyl, or aroyl; R 1 , R 2 , R 4 and R 5 are H, OH, alkyl, cycloalkyl, alkoxy s, halogen, fluorinated alkyl, —CN, —NH—SO 2 -alkyl, -SO 2 —NH-alkyl, alkyl amide, amino, alkylamino s, dialkylamino, fluorinated alkoxy, acyl, aryl, or aroyl; R 3 is H, alkyl, cycloalkyl, alkoxy, fluorinated alkyl, —NH—SO 2 -alkyl, -SO 2 —NH-alkyl, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, aryl, or aroyl; or a pharmaceutically acceptable salt thereof, which are useful in the treatment of central nervous system disorders.

  本发明提供了一种制备1,2,3,4,8,9,10,10a-八氢-7bH-环戊[b][1,4]二氮杂-6,7,1-咪唑[6,7,1-hi]吲哚衍生物的方法，其一般式为：1其中：R为H、烷基、酰基或芳基；R1、R2、R4和R5为H、OH、烷基、环烷基、烷氧基、卤素、氟代烷基、—CN、—NH—SO2-烷基、-SO2—NH-烷基、烷基酰胺、氨基、烷基氨基、二烷基氨基、氟代烷氧基、酰基、芳基或芳基酰基；R3为H、烷基、环烷基、烷氧基、氟代烷基、—NH—SO2-烷基、-SO2—NH-烷基、烷基酰胺、氨基、烷基氨基、二烷基氨基、氟代烷氧基、酰基、芳基或芳基酰基；或其药学上可接受的盐，其用于治疗中枢神经系统疾病。
• Cyclopenta&lsqb;b&rsqb;&lsqb;1,4&rsqb;diazepino&lsqb;6,7,1-hi&rsqb;indoles and derivatives
  申请人：Wyeth

  公开号：US06777407B2

  公开（公告）日：2004-08-17

  This invention provides compounds of the formulae: wherein: R1 is hydrogen, —C(O)CH3 or alkyl of 1-6 carbon atoms; R2 and R3 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, cycloalkyl, alkoxy of 1-6 carbon atoms, —CH2OH, fluoroalkyl, alkyl sulfonamide of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluoroalkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, aryl, or aroyl; R4 and R5 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, halogen, fluoroalkyl, —CN, alkyl sulfonamide of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluoroalkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, or aroyl; R6 and R7 are each independently hydrogen, C1-C6 alkyl or cycloalkyl; or a pharmaceutically acceptable salt thereof, as well as pharmaceutical compositions containing these compounds and methods for their use, including treatment of obsessive-compulsive disorder, panic disorder, depression, anxiety, generalized anxiety disorder, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.

  本发明提供了下列式的化合物：其中：R1为氢、—C（O）CH3或1-6个碳原子的烷基；R2和R3各自独立地为氢、1-6个碳原子的烷基、环烷基、1-6个碳原子的烷氧基、—CH2OH、氟烷基、1-6个碳原子的烷基磺酰胺基、1-6个碳原子的烷基酰胺基、氨基、1-6个碳原子的烷基氨基、每个烷基成分的1-6个碳原子的二烷基氨基、1-6个碳原子的氟烷氧基、2-7个碳原子的酰基、芳基或芳香酰基；R4和R5各自独立地为氢、1-6个碳原子的烷基、1-6个碳原子的烷氧基、卤素、氟烷基、—CN、1-6个碳原子的烷基磺酰胺基、1-6个碳原子的烷基酰胺基、氨基、1-6个碳原子的烷基氨基、每个烷基成分的1-6个碳原子的二烷基氨基、1-6个碳原子的氟烷氧基、2-7个碳原子的酰基或芳香酰基；R6和R7各自独立地为氢、C1-C6烷基或环烷基；或其药学上可接受的盐，以及包含这些化合物的制药组合物和使用它们的方法，包括治疗强迫症、惊恐障碍、抑郁症、焦虑症、广泛性焦虑症、精神分裂症、偏头痛、睡眠障碍、进食障碍、肥胖症、癫痫和脊髓损伤。