methyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate | 69948-64-7

• 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: methyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate
• 英文别名: 4-oxo-4,5,6,7-tetrahydro-indole-2-carboxylic acid methyl ester；4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid methyl ester；methyl 4-oxo-1,5,6,7-tetrahydroindole-2-carboxylate
• CAS: 69948-64-7
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: BZSSQPOUVNSCGF-UHFFFAOYSA-N

物化性质

• 熔点：
  179 °C(Solv: ligroine (8032-32-4))
• 沸点：
  411.8±45.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  methyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate 在 lithium hydroxide monohydrate 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 19.08h， 生成 1-(4-(tert-butoxycarbonyl)benzyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  COMPOUND WITH ANTICANCER ACTIVITY

  摘要：

  提供具有抗癌活性的化合物，或其药用可接受的盐。所使用的化合物表示为以下式（I）或其药用可接受的盐： （其中，L1和L2相同或不同，每个代表从(A)到(F)式组成的一种式子所代表的基团，S代表从(S1)到(S18)式组成的一种式子所代表的基团）。

  公开号：

  US20210024540A1
• 作为产物：
  描述：

  1,5,6,7-四氢-4H-吲哚-4-酮 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 21.08h， 生成 methyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate
  参考文献：
  名称：

  BET DEGRADER

  摘要：

  本发明提供了一种BET（蛋白质）降解剂，具体地说，是一种含有由公式（I）或其药学上可接受的盐所表示的化合物的BET降解剂： 其中L1和L2相同或不同，每个代表BET蛋白质的小分子配体，S代表从公式组成的选择公式所表示的组的群，该组包括（SI）到（S18）的公式。

  公开号：

  EP4039333A1

文献信息

• Pyrrole and pyrazole DAAO inhibitors
  申请人：Fang Kevin Q.

  公开号：US20050143443A1

  公开（公告）日：2005-06-30

  Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein R 1 and R 2 are independently selected from hydrogen, halo, nitro, alkyl, acyl, alkylaryl, and XYR 5 ; or R 1 and R 2 , taken together, form a 5, 6, 7 or 8-membered substituted or unsubstituted carbocyclic or heterocyclic group; X and Y are independently selected from O, S, NH, and (CR 6 R 7 ) n ; R 3 is hydrogen, alkyl or M + ; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc ion or a mixture thereof; Z is N or CR 4 ; R 4 is from selected from hydrogen, halo, nitro, alkyl, alkylaryl, and XYR 5 ; R 5 is selected from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R 6 and R 7 are independently selected from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R 1 , R 2 and R 4 is other than hydrogen; and at least one of X and Y is (CR 6 R 7 ) n . D-serine or cycloserine may be coadministered along with the compound of formula I.

  增加D-丝氨酸浓度和减少D-丝氨酸氧化的有毒产物浓度的方法，用于增强学习、记忆和/或认知能力，或用于治疗精神分裂症、阿尔茨海默病、共济失调或神经病性疼痛，或预防神经元功能丧失，这涉及向需要治疗的受试者施用化合物I的治疗有效量，或其药学上可接受的盐或溶剂：其中R1和R2独立地选自氢、卤素、硝基、烷基、酰基、烷基芳基和XYR5；或R1和R2共同形成一个5、6、7或8-成员的取代或未取代的碳环或杂环基团；X和Y独立地选自O、S、NH和(CR6R7)n；R3为氢、烷基或M+；M为铝、钙、锂、镁、钾、钠、锌离子或其混合物；Z为N或CR4；R4选自氢、卤素、硝基、烷基、烷基芳基和XYR5；R5选自芳基、取代芳基、杂环芳基和取代杂环芳基；R6和R7独立地选自氢和烷基；n为1到6的整数；R1、R2和R4中至少有一个不是氢；X和Y中至少有一个是(CR6R7)n。 D-丝氨酸或环丝氨酸可以与化合物I的共同给药。
• Pyrrole and Pyrazole DAAO Inhibitors
  申请人：Fang Q. Kevin

  公开号：US20100016397A1

  公开（公告）日：2010-01-21

  Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein R 1 and R 2 are independently selected from hydrogen, halo, nitro, alkyl, acyl, alkylaryl, and XYR 5 ; or R 1 and R 2 , taken together, form a 5, 6, 7 or 8-membered substituted or unsubstituted carbocyclic or heterocyclic group; X and Y are independently selected from O, S, NH, and (CR 6 R 7 ) n ; R 3 is hydrogen, alkyl or M + ; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc ion or a mixture thereof; Z is N or CR 4 ; R 4 is from selected from hydrogen, halo, nitro, alkyl, alkylaryl, and XYR 5 ; R 5 is selected from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R 6 and R 7 are independently selected from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R 1 , R 2 and R 4 is other than hydrogen; and at least one of X and Y is (CR 6 R 7 ) n . D-serine or cycloserine may be coadministered along with the compound of formula I.

  增加D-丝氨酸浓度并减少D-丝氨酸氧化产物浓度的方法，以增强学习、记忆和/或认知能力，或治疗精神分裂症、阿尔茨海默病、共济失调或神经病理性疼痛，或预防神经退行性疾病特征性神经元功能损失，包括向需要治疗的受试者施用公式I的化合物或其药学上可接受的盐或溶剂的治疗有效量：其中，R1和R2分别选自氢、卤素、硝基、烷基、酰基、烷基芳基和XYR5；或R1和R2共同形成5、6、7或8成员取代或未取代的碳环或杂环基；X和Y分别选自O、S、NH和（CR6R7）n；R3为氢、烷基或M+；M为铝离子、钙离子、锂离子、镁离子、钾离子、钠离子、锌离子或其混合物；Z为N或CR4；R4选自氢、卤素、硝基、烷基、烷基芳基和XYR5；R5选自芳基、取代芳基、杂芳基和取代杂芳基；R6和R7分别选自氢和烷基；n为1到6的整数；R1、R2和R4中至少有一个不是氢；X和Y中至少有一个是（CR6R7）n。D-丝氨酸或环丝氨酸可以与公式I的化合物一起共同施用。
• INHIBITORS OF D-AMINO ACID OXIDASE
  申请人：Heffernan Michele L. R.

  公开号：US20100029737A1

  公开（公告）日：2010-02-04

  The present invention provides novel inhibitors of the enzyme D-amino acid oxidase. The compounds of the invention are useful for treating or preventing diseases and/or condition, wherein modulation of D-serine levels, and/or its oxidative products, is effective in ameliorating symptoms. The invention further provides methods of enhancing learning, memory and/or cognition. For example, the invention provides methods for treating or preventing loss of memory and/or cognition associated with neurodegenerative diseases, such as Alzheimer's disease. The invention further provides methods for preventing loss of neuronal function characteristic of neurodegenerative diseases. In addition, methods are provided for the treatment or prevention of neuropsychiatric diseases (e.g., schizophrenia) and for the treatment or prevention of pain and ataxia.

  本发明提供了新型D-氨基酸氧化酶酶的抑制剂。本发明的化合物可用于治疗或预防疾病和/或症状，其中调节D-丝氨酸水平和/或其氧化产物对缓解症状有效。本发明还提供了增强学习，记忆和/或认知的方法。例如，本发明提供了用于治疗或预防神经退行性疾病（如阿尔茨海默病）相关的记忆和/或认知丧失的方法。本发明还提供了预防神经退行性疾病特征性神经元功能丧失的方法。此外，还提供了用于治疗或预防神经精神疾病（例如，精神分裂症）和用于治疗或预防疼痛和共济失调的方法。
• PYRROLE AND PYRAZOLE DAAO INHIBITORS
  申请人：FANG Q. Kevin

  公开号：US20110092559A1

  公开（公告）日：2011-04-21

  Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein R 1 and R 2 are independently selected from hydrogen, halo, nitro, alkyl, acyl, alkylaryl, and XYR 5 ; or R 1 and R 2 , taken together, form a 5, 6, 7 or 8-membered substituted or unsubstituted carbocyclic or heterocyclic group; X and Y are independently selected from O, S, NH, and (CR 6 R 7 ) n ; R 3 is hydrogen, alkyl or M + ; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc ion or a mixture thereof; Z is N or CR 4 ; R 4 is from selected from hydrogen, halo, nitro, alkyl, alkylaryl, and XYR 5 ; R 5 is selected from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R 6 and R 7 are independently selected from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R 1 , R 2 and R 4 is other than hydrogen; and at least one of X and Y is (CR 6 R 7 ) n . D-serine or cycloserine may be coadministered along with the compound of formula I.

  增加D-丝氨酸浓度和减少D-丝氨酸氧化的有毒产物浓度的方法，以增强学习、记忆和/或认知能力，或用于治疗精神分裂症、阿尔茨海默病、共济失调或神经病理性疼痛，或预防神经退行性疾病特征性神经元功能丧失，包括向需要治疗的受试者施用公式I的化合物的治疗有效量，或其药学上可接受的盐或溶剂：其中，R1和R2分别选自氢、卤、硝基、烷基、酰基、烷基芳基和XYR5；或R1和R2一起形成一个5、6、7或8成员的取代或未取代的碳环或杂环基；X和Y分别选自O、S、NH和（CR6R7）n；R3是氢、烷基或M+；M是铝、钙、锂、镁、钾、钠、锌离子或其混合物；Z是N或CR4；R4选自氢、卤、硝基、烷基、烷基芳基和XYR5；R5选自芳基、取代芳基、杂芳基和取代杂芳基；R6和R7分别选自氢和烷基；n是1到6的整数；R1、R2和R4中至少有一个不是氢；X和Y中至少有一个是（CR6R7）n。D-丝氨酸或环丝氨酸可以与公式I的化合物一起共同施用。
• Inhibitors of D-amino acid oxidase
  申请人：Sepracor, Inc.

  公开号：US07902252B2

  公开（公告）日：2011-03-08

  The present invention provides novel inhibitors of the enzyme D-amino acid oxidase. The compounds of the invention are useful for treating or preventing diseases and/or condition, wherein modulation of D-serine levels, and/or its oxidative products, is effective in ameliorating symptoms. The invention further provides methods of enhancing learning, memory and/or cognition. For example, the invention provides methods for treating or preventing loss of memory and/or cognition associated with neurodegenerative diseases, such as Alzheimer's disease. The invention further provides methods for preventing loss of neuronal function characteristic of neurodegenerative diseases. In addition, methods are provided for the treatment or prevention of neuropsychiatric diseases (e.g., schizophrenia) and for the treatment or prevention of pain and ataxia.

  本发明提供了新型D-氨基酸氧化酶的抑制剂。本发明的化合物可用于治疗或预防疾病和/或症状，其中调节D-丝氨酸水平及/或其氧化产物可有效缓解症状。此外，本发明还提供了增强学习、记忆和/或认知的方法。例如，本发明提供了用于治疗或预防神经退行性疾病（如阿尔茨海默病）相关的记忆和/或认知损失的方法。本发明还提供了预防神经退行性疾病特征性神经元功能丧失的方法。此外，还提供了治疗或预防神经精神疾病（如精神分裂症）以及治疗或预防疼痛和共济失调的方法。