1-(1-cyclopropylmethyl-piperidin-4-yl)-1H-indole | 170364-86-0

• 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-(1-cyclopropylmethyl-piperidin-4-yl)-1H-indole
• 英文别名: 1-[(1-N-Cyclopropylmethyl)-piperidine-4-yl]-indole；1-N-(1-N-(Cyclopropylmethyl)-piperidin-4-yl)-indole；1-[1-(cyclopropylmethyl)piperidin-4-yl]indole
• CAS: 170364-86-0
• 化学式: C₁₇H₂₂N₂
• 分子量: 254.375
• InChiKey: GMJLKDDVABMGCD-UHFFFAOYSA-N

物化性质

• 沸点：
  403.1±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-cyclopropylmethyl-piperidin-4-yl)-1H-indole 在 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.67h， 生成 3-[1-[1-(cyclopropylmethyl)-4-piperidinyl]-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Strategies for the synthesis of N-(azacycloalkyl)bisindolylmaleimides: selective inhibitors of PKCβ

  摘要：

  N-(Azacycloalkyl)bisindolylmaleimides 1 have been identified to be selective inhibitors of PKCbeta. This manuscript will describe the synthetic approaches employed to prepare this class of compounds that resulted in development of efficient methods for preparation of N-(azacycloalkyl) indole 5, indole-3-acetamide 8 and indole-3-glyoxylate ester 4 derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00973-6
• 作为产物：
  描述：

  4-(吲哚-1-基)哌啶甲酸叔丁酯 在 potassium carbonate 、 三氟乙酸 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 1-(1-cyclopropylmethyl-piperidin-4-yl)-1H-indole
  参考文献：
  名称：

  Strategies for the synthesis of N-(azacycloalkyl)bisindolylmaleimides: selective inhibitors of PKCβ

  摘要：

  N-(Azacycloalkyl)bisindolylmaleimides 1 have been identified to be selective inhibitors of PKCbeta. This manuscript will describe the synthetic approaches employed to prepare this class of compounds that resulted in development of efficient methods for preparation of N-(azacycloalkyl) indole 5, indole-3-acetamide 8 and indole-3-glyoxylate ester 4 derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00973-6

文献信息

• Protein kinase C inhibitors
  申请人：Eli Lilly and Company

  公开号：US05545636A1

  公开（公告）日：1996-08-13

  The present invention discloses compounds of the general formula: ##STR1## The compounds are highly isozyme selective protein kinase C beta-1 and beta-2 isozyme inhibitors. Accordingly, the present invention provides a method of selectively inhibiting protein kinase C isozymes beta-1, and beta-2. As isozyme selective inhibitors of beta-1 and beta-2, the compounds are therapeutically useful in treating conditions associated with diabetes mellitus and its complications, as well as other disease states associated with an elevation of the beta-1 and beta-2 isozyme.

  本发明公开了一般公式的化合物：##STR1## 这些化合物是高度异构酶选择性的蛋白激酶C beta-1和beta-2异构酶抑制剂。因此，本发明提供了一种选择性抑制蛋白激酶C异构酶beta-1和beta-2的方法。作为beta-1和beta-2的异构酶选择性抑制剂，这些化合物在治疗与糖尿病及其并发症相关的疾病状态以及与beta-1和beta-2异构酶升高相关的其他疾病状态方面具有治疗作用。
• [EN] PROTEIN KINASE C INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTEINE-KINASE C
  申请人：ELI LILLY AND COMPANY

  公开号：WO1995017182A1

  公开（公告）日：1995-06-29

  (EN) The present invention discloses compounds that are highly isozyme selective protein kinase C beta-1 and beta-2 isozyme inhibitors. Accordingly, the present invention provides a method of selectively inhibiting protein kinase C isozymes beta-1, and beta-2. As isozyme selective inhibitors of beta-1 and beta-2, the compounds are therapeutically useful in treating conditions associated with diabetes mellitus and its complications, as well as other disease states associated with an elevation of the beta-1 and beta-2 isozymes.(FR) La présente invention décrit des composés qui sont des inhibiteurs des isozymes béta-1 et béta-2 de la protéine-kinase C, qui sont hypersélectifs des isozymes. En conséquence, la présente invention décrit un procédé d'inhibition sélective des isozymes béta-1 et béta-2 de la protéine-kinase C. En temps qu'inhibiteurs sélectifs des isozymes béta-1 et béta-2, ces composés sont thérapeutiquement utiles pour traiter des pathologies associées au diabète sucré et à ses complications, ainsi que d'autres états pathologiques associés à une élévation des isozymes béta-1 et béta-2.

  本发明揭示了高度特异的蛋白激酶C beta-1和beta-2同工酶抑制剂化合物。因此，本发明提供了一种选择性抑制蛋白激酶C同工酶beta-1和beta-2的方法。作为beta-1和beta-2的同工酶选择性抑制剂，这些化合物在治疗与糖尿病及其并发症相关的疾病状态以及与beta-1和beta-2同工酶升高相关的其他疾病状态方面具有治疗用途。
• Protein Kinase C Inhibitors
  申请人：ELI LILLY AND COMPANY

  公开号：EP1449529A1

  公开（公告）日：2004-08-25

  The present invention discloses compounds that are highly isozyme selective protein kinase C beta-1 and beta-2 isozyme inhibitors. Accordingly, the present invention provides a method of selectively inhibiting protein kinase C isozymes beta-1, and beta-2. As isozyme selective inhibitors of beta-1 and beta-2, the compounds are therapeutically useful in treating conditions associated with diabetes mellitus and its complications, as well as other disease states associated with an elevation of the beta-1 and beta-2 isozyme.

  本发明公开了具有高度同工酶选择性的蛋白激酶 C β-1和β-2同工酶抑制剂化合物。因此，本发明提供了一种选择性抑制蛋白激酶 C 同工酶 beta-1 和 beta-2 的方法。作为β-1和β-2的同工酶选择性抑制剂，这些化合物在治疗与糖尿病及其并发症有关的病症以及与β-1和β-2同工酶升高有关的其他疾病状态方面具有治疗作用。
• Acyclic N-(azacycloalkyl)bisindolylmaleimides: isozyme selective inhibitors of PKCβ
  作者：Margaret M Faul、James R Gillig、Michael R Jirousek、Lawrence M Ballas、Theo Schotten、Astrid Kahl、Michael Mohr

  DOI：10.1016/s0960-894x(03)00286-5

  日期：2003.6

  The synthesis and structure-activity relationship (SAR) trends of a new class of N-(azacycloalkyl)bisindolylmaleimides 1, acyclic derivatives of staurosporine, is described. The representative compound for this series (1e) exhibits an IC50 of 40-50 nM against the human PKCbeta(1) and PKCbeta(2) isozymes and selectively inhibits the PKCbeta isozymes in comparison to other PKC isozymes (alpha, gamma, delta, epsilon, lambda, and eta). The series is also kinase selective for PKC in comparison to other ATP-dependent kinases. A comparison of the PKC isozyme and kinase activity of the series is made to the kinase inhibitor staurosporine. (C) 2003 Elsevier Science Ltd. All rights reserved.
• PROTEIN KINASE C INHIBITORS
  申请人：ELI LILLY AND COMPANY

  公开号：EP0817627A1

  公开（公告）日：1998-01-14