1-(2-hydroxy-2-phenylethyl)-6-(ethylthio)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one | 679805-50-6

• 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-hydroxy-2-phenylethyl)-6-(ethylthio)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 6-ethylsulfanyl-1-(2-hydroxy-2-phenylethyl)-5H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 679805-50-6
• 化学式: C₁₅H₁₆N₄O₂S
• 分子量: 316.384
• InChiKey: NXPSFNSDLKKIOP-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C
• 沸点：
  565.7±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-2-phenylethyl)-6-(ethylthio)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 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
• 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 作用下， 以 四氢呋喃 为溶剂， 反应 8.17h， 生成 1-(2-hydroxy-2-phenylethyl)-6-(ethylthio)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
  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
• 作为试剂：
  描述：

  1-(2-羟基-2-苯基乙基)-6-(甲硫基)-1,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮 、 碘乙烷 在 1-(2-hydroxy-2-phenylethyl)-6-(ethylthio)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 、 Silica Gel 、 chloroform methanol 作用下， 以to afford the pure product 8b (2.05 g, 65%) as a light yellow solid的产率得到1-(2-hydroxy-2-phenylethyl)-6-(ethylthio)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Substituted pyrazolo[3,4-D]pyrimidines as anti-tumor agents

  摘要：

  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。

  公开号：

  US07589086B2

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。
• Identification of a Novel Pyrazolo[3,4-<i>d</i>]pyrimidine Able To Inhibit Cell Proliferation of a Human Osteogenic Sarcoma in Vitro and in a Xenograft Model in Mice
  作者：Fabrizio Manetti、Annalisa Santucci、Giada A. Locatelli、Giovanni Maga、Adriano Spreafico、Tommaso Serchi、Maurizio Orlandini、Giulia Bernardini、Nicola P. Caradonna、Andrea Spallarossa、Chiara Brullo、Silvia Schenone、Olga Bruno、Angelo Ranise、Francesco Bondavalli、Oskar Hoffmann、Mauro Bologna、Adriano Angelucci、Maurizio Botta

  DOI：10.1021/jm061449r

  日期：2007.11.1

  New pyrazolo[3,4-d]pyrimidines were synthesized and found to inhibit Src phosphorylation in a cell-free assay. Some of them significantly reduced the growth of human osteogenic sarcoma (SaOS-2) cells. The best compound, in terms of inhibitory properties toward both Src and SaOS-2 cells, was further investigated and found to reduce bone resorption when used to treat mouse osteoclasts, without interfering with normal osteoblast growth. Moreover, its metabolic stability prompted its study on a human SaOS-2 xenograft tumor model in nude mice, where the compound reduced significantly both the volume and weight of the tumor. These experimental findings make the new compound an interesting hit in the field of bone-related diseases.
• 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.
• 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.
• US7589086B2
  申请人：——

  公开号：US7589086B2

  公开（公告）日：2009-09-15