3-((2-cyanoethanoyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester | 1056596-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-((2-cyanoethanoyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 3-(3-cyano-2-oxopropyl)pyrrolidine-1-carboxylate
• CAS: 1056596-64-5
• 化学式: C₁₃H₂₀N₂O₃
• 分子量: 252.313
• InChiKey: VHILUAPVCGIGEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-1'-methyl-1H-1'H-4,4'-bispyrazole. 、 3-((2-cyanoethanoyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester 生成 Tert-butyl 3-[[7-amino-3-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl]methyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Discovery of pyrazolo[1,5-a]pyrimidine-based CHK1 inhibitors: A template-based approach—Part 2

  摘要：

  Previous efforts by our group have established pyrazolo[1,5-a]pyrimidine as a viable core for the development of potent and selective CDK inhibitors. As part of an effort to utilize the pyrazolo[1,5-a]pyrimidine core as a template for the design and synthesis of potent and selective kinase inhibitors, we focused on a key regulator in the cell cycle progression, CHK1. Continued SAR development of the pyrazolo [1,5-a]pyrimidine core at the C5 and C6 positions, in conjunction with previously disclosed SAR at the C3 and C7 positions, led to the discovery of potent and selective CHK1 inhibitors. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.114
• 作为产物：
  描述：

  、 乙腈 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 3-((2-cyanoethanoyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of pyrazolo[1,5-a]pyrimidine-based CHK1 inhibitors: A template-based approach—Part 2

  摘要：

  Previous efforts by our group have established pyrazolo[1,5-a]pyrimidine as a viable core for the development of potent and selective CDK inhibitors. As part of an effort to utilize the pyrazolo[1,5-a]pyrimidine core as a template for the design and synthesis of potent and selective kinase inhibitors, we focused on a key regulator in the cell cycle progression, CHK1. Continued SAR development of the pyrazolo [1,5-a]pyrimidine core at the C5 and C6 positions, in conjunction with previously disclosed SAR at the C3 and C7 positions, led to the discovery of potent and selective CHK1 inhibitors. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.114

文献信息

• Methods for inhibiting protein kinases
  申请人：Guzi J. Timothy

  公开号：US20070082900A1

  公开（公告）日：2007-04-12

  The present invention provides methods for inhibiting protein kinases selected from the group consisting of AKT, Checkpoint kinase, Aurora kinase, Pim kinases, and tyrosine kinase using pyrazolo[1,5-a]pyrimidine compounds and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with protein kinases using such compounds.

  本发明提供了使用吡唑并[1,5-a]嘧啶化合物抑制选自AKT、检查点激酶、极光激酶、Pim激酶和酪氨酸激酶的蛋白激酶的方法，以及使用这些化合物治疗、预防、抑制或改善与蛋白激酶相关的一种或多种疾病的方法。
• USE OF PYRAZOLO [1,5-A] PYRIMIDINE DERIVATIVES FOR INHIBITING KINASES METHODS FOR INHIBITING PROTEIN KINASES
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1942900B1

  公开（公告）日：2015-06-03
• PYRAZOLOPYRIMIDINES AS CYCLIN DEPENDENT KINASE INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2069349B1

  公开（公告）日：2016-06-15
• Novel pyrazolopyrimidines as cyclin dependent kinase inhibitors
  申请人：Guzi J. Timothy

  公开号：US20070072881A1

  公开（公告）日：2007-03-29

  In its many embodiments, the present invention provides a class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases (CDKs), methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.
• METHODS FOR INHIBITING PROTEIN KINASES
  申请人：Guzi Timothy J.

  公开号：US20100125068A1

  公开（公告）日：2010-05-20

  The present invention provides methods for inhibiting protein kinases selected from the group consisting of AKT, Checkpoint kinase, Aurora kinase, Pim kinases, and tyrosine kinase using pyrazolo[1,5-a]pyrimidine compounds and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with protein kinases using such compounds.