1-(2-bromo-2-phenylethyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine | 805326-34-5

• 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-bromo-2-phenylethyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 1-(2-Bromo-2-phenylethyl)-4-chloropyrazolo[3,4-d]pyrimidine
• CAS: 805326-34-5
• 化学式: C₁₃H₁₀BrClN₄
• 分子量: 337.606
• InChiKey: RIVMSXFQRIFPSV-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  453.4±45.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-bromo-2-phenylethyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine 、 环己亚胺 以 甲苯 为溶剂， 反应 36.0h， 以64%的产率得到4-(Azepan-1-yl)-1-(2-bromo-2-phenyl-ethyl)pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Pyrazolo[3,4-d]pyrimidines as Potent Antiproliferative and Proapoptotic Agents toward A431 and 8701-BC Cells in Culture via Inhibition of c-Src Phosphorylation

  摘要：

  We report here the synthesis of new pyrazolo[3,4-d]pyrimidine derivatives along with their biological properties as inhibitors of isolated Src and cell line proliferation (A431 and 8701-BC cells). Such compounds block the growth of cancer cells by interfering with the phosphorylation of Src, and they act as proapoptotic agents through the inhibition of the anti apoptotic gene BCL2. Several of them were found to be more active than the reference compound (1-(tert-butyl)-3-(4-chlorophenyl)-4-aminopyrazolo[3,4-d]pyrimidine, PP2) in inhibiting cell proliferation and in inducing apoptosis, and as active as PP2 in the inhibition of the phosphorylation of isolated Src. Moreover, molecular modeling simulations have been performed to hypothesize the way, at the molecular level, by which the inhibitors were able to act as antiproliferative agents.

  DOI：

  10.1021/jm050603r
• 作为产物：
  描述：

  5-氨基-1-(2-羟基-2-苯基乙基)-1H-吡唑-4-羧酸乙酯 在 吡啶 、 三溴化磷 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 92.0h， 生成 1-(2-bromo-2-phenylethyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Pyrazolo[3,4-d]pyrimidines as Potent Antiproliferative and Proapoptotic Agents toward A431 and 8701-BC Cells in Culture via Inhibition of c-Src Phosphorylation

  摘要：

  We report here the synthesis of new pyrazolo[3,4-d]pyrimidine derivatives along with their biological properties as inhibitors of isolated Src and cell line proliferation (A431 and 8701-BC cells). Such compounds block the growth of cancer cells by interfering with the phosphorylation of Src, and they act as proapoptotic agents through the inhibition of the anti apoptotic gene BCL2. Several of them were found to be more active than the reference compound (1-(tert-butyl)-3-(4-chlorophenyl)-4-aminopyrazolo[3,4-d]pyrimidine, PP2) in inhibiting cell proliferation and in inducing apoptosis, and as active as PP2 in the inhibition of the phosphorylation of isolated Src. Moreover, molecular modeling simulations have been performed to hypothesize the way, at the molecular level, by which the inhibitors were able to act as antiproliferative agents.

  DOI：

  10.1021/jm050603r

文献信息

• 4-Substituted derivatives of pyrazolo[3,4-d]pyrimidine and pyrrolo[2,3-d]pyrimidine and uses thereof
  申请人：Bondavalli Francesco

  公开号：US20070010510A1

  公开（公告）日：2007-01-11

  4-Substituted derivatives of pyrazolo[3,4-d]pyrimidine and pyrrolo[2,3-d]pyrimidine are described. Compounds are active as antitumoural agents.

  本文描述了嘧唑并[3,4-d]嘧啶和吡咯并[2,3-d]嘧啶的4-取代衍生物。这些化合物作为抗肿瘤剂具有活性。
• [EN] 4-SUBSTITUTED DERIVATIVES OF PYRAZOLO [3,4-d] PYRIMIDINE AND PYRROLO [2,3-d] PYRIMIDINE AND USES THEREOF<br/>[FR] DERIVES SUBSTITUES EN 4 DE PYRAZOLO[3,4-D]PYRIMIDINE ET PYRROLO[2,3-D]PYRIMIDINE ET UTILISATIONS ASSOCIEES
  申请人：UNIV SIENA

  公开号：WO2004106340A3

  公开（公告）日：2005-02-17
• 4-SUBSTITUTED DERIVATIVES OF PYRAZOLO ¬3,4-d PYRIMIDINE AND USES THEREOF
  申请人：UNIVERSITA DEGLI STUDI DI SIENA

  公开号：EP1638966B1

  公开（公告）日：2008-03-19
• US7589086B2
  申请人：——

  公开号：US7589086B2

  公开（公告）日：2009-09-15