2-(4-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-phenylethanol | 679805-56-2

• 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: 2-(4-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-phenylethanol
• 英文别名: 2-(4-Bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-phenylethanol；2-(4-bromopyrazolo[3,4-d]pyrimidin-1-yl)-1-phenylethanol
• CAS: 679805-56-2
• 化学式: C₁₃H₁₁BrN₄O
• 分子量: 319.161
• InChiKey: YSNOUNHMBVABAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  正丁胺 、 2-(4-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-phenylethanol 以 甲苯 为溶剂， 反应 24.0h， 以80%的产率得到2-[4-(Butylamino)pyrazolo[3,4-d]pyrimidin-1-yl]-1-phenylethanol
  参考文献：
  名称：

  Pyrazolo[3,4-d]pyrimidines Endowed with Antiproliferative Activity on Ductal Infiltrating Carcinoma Cells

  摘要：

  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.

  DOI：

  10.1021/jm034257u
• 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 N-溴代丁二酰亚胺(NBS) 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 8.0h， 生成 2-(4-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-phenylethanol
  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

• 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。
• Substituted pyrazolo[3,4-D]pyrimidines as anti-tumor agents
  申请人：Universita degli Studi di Siena

  公开号：US07589086B2

  公开（公告）日：2009-09-15

  The present invention provides a compound of pyrazolo[3,4-d]pyrimidine having the formula wherein: X=N; R=H, alkylthio, or aminoalkylthio; R1=NHcyclopropyl, NHC3H7, NHC4H9, N(CH2CH3)2, NHCH2CH2OC2H5, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, NHcyclohexyl, 1-hexahydroazepinyl, NHCH2C6H5, or NHCH2CH2C6H5; wherein R3=H, halogen, or alkyl and R5=Cl, Br or OH.

  本发明提供一种具有以下式的吡唑并[3,4-d]嘧啶化合物：其中： X = N; R = H，烷基硫或氨基烷基硫; R1 = NH环丙基，NHC3H7，NHC4H9，N（CH2CH3）2，NHCH2CH2OC2H5，1-吡咯烷基，1-哌啶基，4-吗啉基，NH环己基，1-六氢噁啉基，NHCH2C6H5或NHCH2CH2C6H5; 其中R3 = H，卤素或烷基，R5 = Cl，Br或OH。
• 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.
• [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