tert-butyl 1,2,3,4-tetrahydropyrazino<1,2-a>indole-2-carboxylate | 131849-17-7

• 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: tert-butyl 1,2,3,4-tetrahydropyrazino<1,2-a>indole-2-carboxylate
• 英文别名: 3,4-dihydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester；t-butyl 1,2,3,4-tetrahydropyrazino[1,2-a]indole-2-carboxylate；tert-butyl 3,4-dihydro-1H-pyrazino[1,2-a]indole-2-carboxylate
• CAS: 131849-17-7
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: QEKSLLZNUWBAPP-UHFFFAOYSA-N

物化性质

• 沸点：
  429.5±38.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 1,2,3,4-tetrahydropyrazino<1,2-a>indole-2-carboxylate 在 盐酸 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 35.5h， 生成 3-(1,2,3,4-tetrahydropyrazino<1,2-a>indol-10-yl)-4-(1-methyl-3-indolyl)-2,5-furandione hydrochloride
  参考文献：
  名称：

  Inhibitors of protein kinase C. 3. Potent and highly selective bisindolylmaleimides by conformational restriction

  摘要：

  The protein kinase inhibitor staurosporine has been used to design a series of selective bisindolylmaleimide inhibitors of protein kinase C (PKC). Guided by molecular graphics, conformational restriction of the cationic side chain has led to ATP competitive inhibitors of improved potency and selectivity. Two compounds have been further evaluated and were shown to inhibit PKC of human origin and prevent T-cell activation in a human allogeneic mixed lymphocyte reaction. One of these compounds was orally absorbed in mice and antagonized a phorbol ester induced paw edema in a dose-dependent manner. This compound also selectively inhibited the secondary T-cell mediated response in a developing adjuvant arthritis model in rats and provides evidence for the potential use of PKC inhibitors as therapeutic immunomodulators.

  DOI：

  10.1021/jm00053a003
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1,2,3,4-四氢吡嗪o[1,2-a]吲哚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl 1,2,3,4-tetrahydropyrazino<1,2-a>indole-2-carboxylate
  参考文献：
  名称：

  4-\x9b3-indolyl!-1H-pyrrolone

  摘要：

  公式的化合物，其中R是氢或羟基，R1和R2共同构成组--(CH2)m--，R7是氢或R1和R7共同构成组--(CH2)n--，且R2是氢；R3是一种芳香族或芳香杂环群；R4、R5和R6各自独立地为氢、卤素、烷基、羟基、烷氧基、卤代烷基、硝基、氨基、酰氨基、烷基硫醚、烷基亚磺酰基或烷基磺酰基；R8是组--(CH2)p--R9或--(CH2)q--R10；R9是氢、烷基碳酰基、氨基烷基碳酰基、氰基、脒基、烷氧基碳酰基、芳氧基碳酰基、烷基磺酰基、氨基甲酰基或硫代氨基甲酰基；R10是羟基、烷氧基、卤素、氨基、一烷基胺、二烷基胺、三烷基胺、叠氮基、酰氨基、烷基磺酰氨基、一个5或6成员的饱和含氮杂环；X和Y是氧；Z是CH；m、p和q各自独立地为0到5的整数，n为1到5的整数，以及作为药物可接受的盐，其在控制炎症、免疫、肿瘤、支气管肺或心血管疾病方面是有用的。

  公开号：

  US05721245A1

文献信息

• Indol-3-yl-carbonyl-spiro-piperidine derivatives as Vla receptor antagonists
  申请人：Bissantz Caterina

  公开号：US20070027173A1

  公开（公告）日：2007-02-01

  The invention relates to indol-3-yl-carbonyl-spiro-piperidine derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the spiro-piperidine head group A and the residues R 1 , R 2 and R 3 are as defined herein. The invention further relates to pharmaceutical compositions containing such compounds, methods for preparing the compounds and pharmaceutical compositions, and their use in the treatment of dysmenorrhea, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, obsessive compulsive disorder, anxious and depressive disorders.

  本发明涉及作为V1a受体拮抗剂的吲哚-3-基-甲酰基-螺环-哌啶衍生物，其由公式I表示：其中，螺环-哌啶头基A以及残基R1、R2和R3如本文所述定义。本发明进一步涉及含有此类化合物的药物组合物，制备化合物和药物组合物的方法，以及它们在治疗痛经、高血压、慢性心力衰竭、血管升压素不适当分泌、肝硬化、肾病综合征、强迫症、焦虑和抑郁障碍中的用途。
• Indol-3-y-carbonyl-piperidin and piperazin-derivatives
  申请人：Bissantz Caterina

  公开号：US20070027163A1

  公开（公告）日：2007-02-01

  The present invention relates to indol-3-yl-carbonyl-piperidin and piperazin derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the residues R 1 to R 3 are as defined herein. The invention also relates to pharmaceutical compositions containing such compounds, and methods for preparation of the compounds and compositions. The invention further relates to methods for treating dysmenorrhea, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, obsessive compulsive disorder, anxiety and depressive disorders.

  本发明涉及作为V1a受体拮抗剂的吲哒-3-基甲酰哌啶和哌嗪衍生物，其由以下式I表示：其中残基R1至R3如本文所定义。该发明还涉及含有这种化合物的药物组合物，以及制备这些化合物和组合物的方法。该发明还涉及治疗痛经、高血压、慢性心力衰竭、抗利尿素过度分泌、肝硬化、肾病综合征、强迫症、焦虑和抑郁症的方法。
• Indol-3-yl-carbonyl-spiro-piperidine derivatives as V1a receptor antagonists
  申请人：Hoffmann-La Roche Inc.

  公开号：US07332501B2

  公开（公告）日：2008-02-19

  The invention relates to indol-3-yl-carbonyl-spiro-piperidine derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the spiro-piperidine head group A and the residues R1, R2 and R3 are as defined herein. The invention further relates to pharmaceutical compositions containing such compounds, methods for preparing the compounds and pharmaceutical compositions, and their use in the treatment of dysmenorrhea, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, obsessive compulsive disorder, anxious and depressive disorders.

  本发明涉及indol-3-yl-carbonyl-spiro-piperidine衍生物，其作为V1a受体拮抗剂，并由式I表示：其中spiro-piperidine头基A和残基R1、R2和R3如本文所定义。本发明还涉及含有此类化合物的制药组合物、制备该化合物和制药组合物的方法，以及它们在治疗痛经、高血压、慢性心力衰竭、不适当分泌加压素、肝硬化、肾病综合征、强迫症和焦虑抑郁症方面的用途。
• INDOL-3-YL-CARBONYL-SPIRO-PIPERIDINE DERIVATIVES AS VIa RECEPTOR ANTAGONISTS
  申请人：Bissantz Caterina

  公开号：US20080146557A1

  公开（公告）日：2008-06-19

  The invention relates to indol-3-yl-carbonyl-spiro-piperidine derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the spiro-piperidine head group A and the residues R 1 , R 2 and R 3 are as defined herein. The invention further relates to pharmaceutical compositions containing such compounds, methods for preparing the compounds and pharmaceutical compositions, and their use in the treatment of dysmenorrhea, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, obsessive compulsive disorder, anxious and depressive disorders.

  本发明涉及一种作为V1a受体拮抗剂的吲哚-3-基-羰基-螺-哌啶衍生物，其由式I表示：其中，螺-哌啶头基A和残基R1、R2和R3如本文所定义。本发明还涉及含有这种化合物的药物组合物、制备这种化合物和药物组合物的方法，以及它们在治疗痛经、高血压、慢性心力衰竭、抗利尿激素不适当分泌、肝硬化、肾病综合征、强迫症和焦虑抑郁症方面的用途。
• INDOL-3-Y-CARBONYL-PIPERIDIN AND PIPERAZIN-DERIVATIVES
  申请人：Bissantz Caterina

  公开号：US20120040990A1

  公开（公告）日：2012-02-16

  The present invention relates to indol-3-yl-carbonyl-piperidin and piperazin derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the residues R 1 to R 3 are as defined herein. The invention also relates to pharmaceutical compositions containing such compounds, and methods for preparation of the compounds and compositions. The invention further relates to methods for treating dysmenorrhea, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, obsessive compulsive disorder, anxiety and depressive disorders.

  本发明涉及一种作为V1a受体拮抗剂的吲哚-3-基甲酰基哌啶和哌嗪衍生物，其由式I表示：其中残基R1至R3如本文所定义。本发明还涉及含有此类化合物的制药组合物，以及制备该化合物和组合物的方法。本发明还涉及治疗痛经、高血压、慢性心力衰竭、不适当分泌加压素、肝硬化、肾病综合征、强迫症、焦虑和抑郁症的方法。