1-[2-(4-chlorophenyl)-2-hydroxyethyl]-6-thioxo-1,5,6,7-tetrahydro-4H-pyrazolo[3,4-d]pyrimidin-4-one | 959772-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-[2-(4-chlorophenyl)-2-hydroxyethyl]-6-thioxo-1,5,6,7-tetrahydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 1-[2-(4-chlorophenyl)-2-hydroxyethyl]-6-sulfanylidene-7H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 959772-26-0
• 化学式: C₁₃H₁₁ClN₄O₂S
• 分子量: 322.775
• InChiKey: SIOJFHASOWPHPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 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：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(4-chlorophenyl)-2-hydroxyethyl]-6-thioxo-1,5,6,7-tetrahydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 、 1-碘代丙烷 以 四氢呋喃 为溶剂， 以68%的产率得到1-(2-hydroxy-2-phenylethyl)-6-propylsulfanyl-5H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Identification of a Novel Pyrazolo[3,4-d]pyrimidine Able To Inhibit Cell Proliferation of a Human Osteogenic Sarcoma in Vitro and in a Xenograft Model in Mice

  摘要：

  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.

  DOI：

  10.1021/jm061449r
• 作为产物：
  描述：

  ethyl 5-{[(benzoylamino)carbonothioyl]amino}-1-[2-(4-chlorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate 在 sodium hydroxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.17h， 生成 1-[2-(4-chlorophenyl)-2-hydroxyethyl]-6-thioxo-1,5,6,7-tetrahydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Identification of a Novel Pyrazolo[3,4-d]pyrimidine Able To Inhibit Cell Proliferation of a Human Osteogenic Sarcoma in Vitro and in a Xenograft Model in Mice

  摘要：

  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.

  DOI：

  10.1021/jm061449r

文献信息

• NEW 4-SUBSTITUTED DERIVATIVES OF PYRAZOLO[3,4-D PYRIMIDINE AND PYRROLO[2,3-D]PYRIMIDINE AND USES THEREOF
  申请人：Schenone Silvia

  公开号：US20100249152A1

  公开（公告）日：2010-09-30

  The present invention relates to a compound 4-substituted derivative of pyrazolo[3,4-d]pyrimidine or of pyrrolo[2,3-d]pyrimidine having the formula (I) and uses thereof, in particular for the treatment of bone related diseases and tumours.

  本发明涉及具有以下式(I)的吡唑并[3,4-d]嘧啶或吡咯[2,3-d]嘧啶的化合物4-取代衍生物及其用途，特别是用于骨相关疾病和肿瘤的治疗。
• NEW 4-SUBSTITUTED DERIVATIVES OF PYRAZOLO [3,4-D] PYRIMIDINE AND PYRROLO [2,3-D] PYRIMIDINE AND USES THEREOF
  申请人：Universita Degli Studi di Siena

  公开号：EP2201013B1

  公开（公告）日：2014-11-19