N'-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-N,N-dimethylethane-1,2-diamine | 871464-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N'-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-N,N-dimethylethane-1,2-diamine
• 英文别名: N-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-N',N'-dimethylethane-1,2-diamine
• CAS: 871464-70-9
• 化学式: C₁₅H₂₅ClN₄
• 分子量: 296.843
• InChiKey: FTNLUPCHUVTWHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-N,N-dimethylethane-1,2-diamine 、 3-溴-4-氯-1H-吡唑啉并嘧啶 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 生成 N'-{3-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-5-chloro-2-methylphenyl}-N,N-dimethylethane-1,2-diamine
  参考文献：
  名称：

  Design and evaluation of a series of pyrazolopyrimidines as p70S6K inhibitors

  摘要：

  The 70-kDa ribosomal protein S6 kinase (p70S6K) is part of the PI3K/AKT/mTOR pathway and has been implicated in cancer. High throughput screening versus p70S6K led to the identification of aminopyrimidine 3a as active inhibitor. Lead optimization of 3a resulted in highly potent, selective, and orally bioavailable pyrazolopyrimidines. In this manuscript we report the structure-activity relationship of this series and pharmacokinetic, pharmacodynamic, and efficacy data of the lead compound 13c. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.105
• 作为产物：
  描述：

  5-氯-3-碘-2-甲基苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 盐酸 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二乙二醇二甲醚 为溶剂， 反应 44.03h， 生成 N'-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-N,N-dimethylethane-1,2-diamine
  参考文献：
  名称：

  [EN] KINASE MODULATORS AND METHODS OF USE
  [FR] MODULATEURS DES PROTEINES KINASES ET LEURS METHODES D'UTILISATION

  摘要：

  公开号：

  WO2005117909A3

文献信息

• [EN] KINASE MODULATORS AND METHODS OF USE<br/>[FR] MODULATEURS DES PROTEINES KINASES ET LEURS METHODES D'UTILISATION
  申请人：EXELIXIS INC

  公开号：WO2005117909A3

  公开（公告）日：2006-04-27
• Design and evaluation of a series of pyrazolopyrimidines as p70S6K inhibitors
  作者：Joerg Bussenius、Neel K. Anand、Charles M. Blazey、Owen J. Bowles、Lynne Canne Bannen、Diva S.-M. Chan、Baili Chen、Erick W. Co、Simona Costanzo、Steven C. DeFina、Larisa Dubenko、Stefan Engst、Maurizio Franzini、Ping Huang、Vasu Jammalamadaka、Richard G. Khoury、Moon H. Kim、Rhett R. Klein、Douglas Laird、Donna T. Le、Morrison B. Mac、David J. Matthews、David Markby、Nicole Miller、John M. Nuss、Jason J. Parks、Tsze H. Tsang、Amy L. Tsuhako、Yong Wang、Wei Xu、Kenneth D. Rice

  DOI：10.1016/j.bmcl.2012.01.105

  日期：2012.3

  The 70-kDa ribosomal protein S6 kinase (p70S6K) is part of the PI3K/AKT/mTOR pathway and has been implicated in cancer. High throughput screening versus p70S6K led to the identification of aminopyrimidine 3a as active inhibitor. Lead optimization of 3a resulted in highly potent, selective, and orally bioavailable pyrazolopyrimidines. In this manuscript we report the structure-activity relationship of this series and pharmacokinetic, pharmacodynamic, and efficacy data of the lead compound 13c. (C) 2012 Elsevier Ltd. All rights reserved.