ethyl 5-{[(benzoylamino)carbonothioyl]amino}-1-[2-(4-fluorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-{[(benzoylamino)carbonothioyl]amino}-1-[2-(4-fluorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate
• 英文别名: Ethyl 5-(benzoylcarbamothioylamino)-1-[2-(4-fluorophenyl)-2-hydroxyethyl]pyrazole-4-carboxylate
• 化学式: C₂₂H₂₁FN₄O₄S
• 分子量: 456.498
• InChiKey: CYMZSUIAWWONDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-{[(benzoylamino)carbonothioyl]amino}-1-[2-(4-fluorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate 在 sodium hydroxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 12.17h， 以75%的产率得到1-[2-(4-fluorophenyl)-2-hydroxyethyl]-6-thioxo-1,5,6,7-tetrahydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  NEW 4-SUBSTITUTED DERIVATIVES OF PYRAZOLO[3,4-D PYRIMIDINE AND PYRROLO[2,3-D]PYRIMIDINE AND USES THEREOF

  摘要：

  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。

  公开号：

  US20100249152A1
• 作为产物：
  描述：

  ethyl 5-amino-1-[2-(4-fluorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate 、 苯甲酰基异硫氰酸酯 以 四氢呋喃 为溶剂， 反应 12.0h， 以85%的产率得到ethyl 5-{[(benzoylamino)carbonothioyl]amino}-1-[2-(4-fluorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  NEW 4-SUBSTITUTED DERIVATIVES OF PYRAZOLO[3,4-D PYRIMIDINE AND PYRROLO[2,3-D]PYRIMIDINE AND USES THEREOF

  摘要：

  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。

  公开号：

  US20100249152A1

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
• 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.