1-(2-chloro-2-phenylethyl)-6-(ethylthio)-4-morpholino-1H-pyrazolo[3,4-d]pyrimidine | 679805-39-1

• 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)-6-(ethylthio)-4-morpholino-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 4-[1-(2-chloro-2-phenylethyl)-6-ethylsulfanylpyrazolo[3,4-d]pyrimidin-4-yl]morpholine
• CAS: 679805-39-1
• 化学式: C₁₉H₂₂ClN₅OS
• 分子量: 403.936
• InChiKey: PCYWYCYVYPEYJS-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C
• 沸点：
  617.8±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-2-phenylethyl)-6-(ethylthio)-4-morpholino-1H-pyrazolo[3,4-d]pyrimidine 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以65%的产率得到4-[6-ethylsulfanyl-1-(2-phenylethenyl)pyrazolo[3,4-d]pyrimidin-4-yl]morpholine
  参考文献：
  名称：

  New pyrazolo[3,4-d]pyrimidines endowed with A431 antiproliferative activity and inhibitory properties of Src phosphorylation

  摘要：

  New 4-aminopyrazolo[3,4-d]pyrimidines bearing various substituents at the position I and 6, were synthesized. The new compounds showed antiproliferative activity toward A431 cells, were found to be inhibitors of Src phosphorylation, and induced apoptotic cell death. In particular, 2h was a better inhibitor of Src phosphorylation than the reference compound PP2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.013
• 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 sodium hydroxide 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 8.17h， 生成 1-(2-chloro-2-phenylethyl)-6-(ethylthio)-4-morpholino-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  New pyrazolo[3,4-d]pyrimidines endowed with A431 antiproliferative activity and inhibitory properties of Src phosphorylation

  摘要：

  New 4-aminopyrazolo[3,4-d]pyrimidines bearing various substituents at the position I and 6, were synthesized. The new compounds showed antiproliferative activity toward A431 cells, were found to be inhibitors of Src phosphorylation, and induced apoptotic cell death. In particular, 2h was a better inhibitor of Src phosphorylation than the reference compound PP2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.013

文献信息

• Pyrazolo[3,4-<i>d</i>]pyrimidines Endowed with Antiproliferative Activity on Ductal Infiltrating Carcinoma Cells
  作者：Fabio Carraro、Annalisa Pucci、Antonella Naldini、Silvia Schenone、Olga Bruno、Angelo Ranise、Francesco Bondavalli、Chiara Brullo、Paola Fossa、Giulia Menozzi、Luisa Mosti、Fabrizio Manetti、Maurizio Botta

  DOI：10.1021/jm034257u

  日期：2004.3.1

  Novel 1,4,6-trisubstituted pyrazolo[3,4-d]pyrimidines are reported with preliminary in vitro activity data indicating that several of them are potent inhibitors (better than the reference compound) of Src phosphorylation of the breast cancer cells 8701-BC, known to overexpress Src. The ability of such compounds to significantly reduce 8701-BC cell proliferation suggests that this scaffold could be a promising lead for the development of antitumoral agents able to block Src phosphorylation of breast cancer cells.
• New pyrazolo[3,4-d]pyrimidines endowed with A431 antiproliferative activity and inhibitory properties of Src phosphorylation
  作者：S. Schenone、O. Bruno、A. Ranise、F. Bondavalli、C. Brullo、P. Fossa、L. Mosti、G. Menozzi、F. Carraro、A. Naldini、C. Bernini、F. Manetti、M. Botta

  DOI：10.1016/j.bmcl.2004.03.013

  日期：2004.5

  New 4-aminopyrazolo[3,4-d]pyrimidines bearing various substituents at the position I and 6, were synthesized. The new compounds showed antiproliferative activity toward A431 cells, were found to be inhibitors of Src phosphorylation, and induced apoptotic cell death. In particular, 2h was a better inhibitor of Src phosphorylation than the reference compound PP2. (C) 2004 Elsevier Ltd. All rights reserved.
• Pyrazolo[3,4-<i>d</i>]pyrimidines as Potent Antiproliferative and Proapoptotic Agents toward A431 and 8701-BC Cells in Culture via Inhibition of c-Src Phosphorylation
  作者：Fabio Carraro、Antonella Naldini、Annalisa Pucci、Giada A. Locatelli、Giovanni Maga、Silvia Schenone、Olga Bruno、Angelo Ranise、Francesco Bondavalli、Chiara Brullo、Paola Fossa、Giulia Menozzi、Luisa Mosti、Michele Modugno、Cristina Tintori、Fabrizio Manetti、Maurizio Botta

  DOI：10.1021/jm050603r

  日期：2006.3.1

  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.