1-(2-chloro-2-phenylethyl)-N6,N6-dimethyl-N4-propyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine | 1104076-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 1-(2-chloro-2-phenylethyl)-N6,N6-dimethyl-N4-propyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
• 英文别名: 1-(2-chloro-2-phenylethyl)-6-N,6-N-dimethyl-4-N-propylpyrazolo[3,4-d]pyrimidine-4,6-diamine
• CAS: 1104076-32-5
• 化学式: C₁₈H₂₃ClN₆
• 分子量: 358.874
• InChiKey: ORSJMRYJQKLLEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-2-phenylethyl)-N6,N6-dimethyl-N4-propyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine 在 Chiralpak AS 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 、
  参考文献：
  名称：

  具有抗炎活性的抗癌吡唑并嘧啶的命中鉴定和生物学评价

  摘要：

  抑制COX：将具有抗增殖作用的吡唑并嘧啶类小文库提交针对两种COX亚型的虚拟筛选。在计算机上鉴定出三种化合物可能是选择性COX-2抑制剂。生物学测定证实其中一种是COX-2抑制剂，其效力和选择性可与已知药物媲美。

  DOI：

  10.1002/cmdc.201000165
• 作为产物：
  描述：

  正丙胺 、 4-chloro-1-(2-chloro-2-phenylethyl)-N,N-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine 以 甲苯 为溶剂， 以51%的产率得到1-(2-chloro-2-phenylethyl)-N6,N6-dimethyl-N4-propyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
  参考文献：
  名称：

  Synthesis, biological evaluation and docking studies of 4-amino substituted 1H-pyrazolo[3,4-d]pyrimidines

  摘要：

  The synthesis of new 4-amino substituted pyrazolo[3,4-d]pyrimidines along with their activity in cell-free enzymatic assays on Src and Abl tyrosine kinases is reported. Some compounds emerged as good dual inhibitors of the two enzymes, showed antiproliferative effects on two Bcr-Abl positive leukemia cell lines K-562 and KU-812, and induced apoptosis, as demonstrated by the PARP assay. Docking studies have been also performed to analyze the binding mode of compounds under study and to identify the structural determinants of their interaction with both Src and Abl. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.034

文献信息

• Anti-proliferative substituted pyrazolo[3,4-d]pyrimidines derivatives (SPP) to inhibit immune activation, virus replication and tumor growth
  申请人：Lori Franco

  公开号：US20120022048A1

  公开（公告）日：2012-01-26

  A family of pyrazolo[3,4-d]pyrimidine derivatives (SPPs) with different substituents on the pyrimidine and pyrazolo rings have been characterized with a panel of tests demonstrating their effects in cell proliferation, toxicity, apoptosis and inhibition of virus replication. We have identified compounds and molecular structures suitable for the treatment of viral infection because they have antiviral activity, anti-proliferative activity or, preferably, both so that, as a single molecule, they both limit T cell hyperactivation and inhibit virus replication. These compounds are not toxic at effective concentrations and are poorly apoptotic. Other nontoxic compounds within this family with excellent anti-proliferative and apoptotic features are potentially effective as anti-cancer drugs.
• Synthesis, biological evaluation and docking studies of 4-amino substituted 1H-pyrazolo[3,4-d]pyrimidines
  作者：Silvia Schenone、Chiara Brullo、Olga Bruno、Francesco Bondavalli、Luisa Mosti、Giovanni Maga、Emmanuele Crespan、Fabio Carraro、Fabrizio Manetti、Cristina Tintori、Maurizio Botta

  DOI：10.1016/j.ejmech.2008.01.034

  日期：2008.12

  The synthesis of new 4-amino substituted pyrazolo[3,4-d]pyrimidines along with their activity in cell-free enzymatic assays on Src and Abl tyrosine kinases is reported. Some compounds emerged as good dual inhibitors of the two enzymes, showed antiproliferative effects on two Bcr-Abl positive leukemia cell lines K-562 and KU-812, and induced apoptosis, as demonstrated by the PARP assay. Docking studies have been also performed to analyze the binding mode of compounds under study and to identify the structural determinants of their interaction with both Src and Abl. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Hit Identification and Biological Evaluation of Anticancer Pyrazolopyrimidines Endowed with Anti-inflammatory Activity
  作者：Stefano Alcaro、Anna Artese、Maurizio Botta、Alessandra T. Zizzari、Francisco Orallo、Francesco Ortuso、Silvia Schenone、Chiara Brullo、Matilde Yáñez

  DOI：10.1002/cmdc.201000165

  日期：——

  Inhibiting COX: A small library of pyrazolopyriminines endowed with antiproliferative action was submitted to virtual screening against two COX isoforms. Three compounds were identified in silico as potentially selective COX‐2 inhibitors. The biological assay confirmed one of them to be a COX‐2 inhibitor with potency and selectivity comparable to known drugs.

  抑制COX：将具有抗增殖作用的吡唑并嘧啶类小文库提交针对两种COX亚型的虚拟筛选。在计算机上鉴定出三种化合物可能是选择性COX-2抑制剂。生物学测定证实其中一种是COX-2抑制剂，其效力和选择性可与已知药物媲美。