ethyl 5-amino-1-[2-(4-chlorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate | 959772-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-amino-1-[2-(4-chlorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate
• 英文别名: Ethyl 5-amino-1-[2-(4-chlorophenyl)-2-hydroxyethyl]pyrazole-4-carboxylate
• CAS: 959772-15-7
• 化学式: C₁₄H₁₆ClN₃O₃
• 分子量: 309.752
• InChiKey: VBCZFWVYXJUURZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-1-[2-(4-chlorophenyl)-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， 生成 ethyl 5-{[(benzoylamino)carbonothioyl]amino}-1-[2-(4-chlorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate
  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：

  1-(4-chlorophenyl)-2-hydrazinoethanol 、 2-氰基-3-乙氧基丙烯酸乙酯 以 甲苯 为溶剂， 反应 8.0h， 以75%的产率得到ethyl 5-amino-1-[2-(4-chlorophenyl)-2-hydroxyethyl]-1H-pyrazole-4-carboxylate
  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

• Structure-Based Optimization of Pyrazolo[3,4-<i>d</i>]pyrimidines as Abl Inhibitors and Antiproliferative Agents toward Human Leukemia Cell Lines
  作者：Fabrizio Manetti、Chiara Brullo、Matteo Magnani、Francesca Mosci、Beatrice Chelli、Emmanuele Crespan、Silvia Schenone、Antonella Naldini、Olga Bruno、Maria Letizia Trincavelli、Giovanni Maga、Fabio Carraro、Claudia Martini、Francesco Bondavalli、Maurizio Botta

  DOI：10.1021/jm701240c

  日期：2008.3.13

  Results from molecular docking calculations and Grid mapping laid the foundations for a structure-based optimization approach to improve the biological properties of pyrazolo-pyrimidine derivatives in terms of inhibition of Abl enzymatic activity and anti proliferative properties toward human leukemia cells. Insertion of halogen substituents with various substitution patterns, suggested by simulations, led to a significant improvement of leukemia cell growth inhibition and to an increase up to 1 order of magnitude of the affinity toward Abl.
• 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