6-[4-[(2,3-Difluorophenyl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine | 1166814-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-[4-[(2,3-Difluorophenyl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine
• 英文别名: 6-[4-[(2,3-difluorophenyl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine
• CAS: 1166814-39-6
• 化学式: C₁₇H₁₅F₅N₆
• 分子量: 398.338
• InChiKey: DZXZQRMALFTZJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 41.0h， 生成 6-[4-[(2,3-Difluorophenyl)methyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine
  参考文献：
  名称：

  Discovery of AZD3514, a small-molecule androgen receptor downregulator for treatment of advanced prostate cancer

  摘要：

  Removal of the basic piperazine nitrogen atom, introduction of a solubilising end group and partial reduction of the triazolopyridazine moiety in the previously-described lead androgen receptor downregulator 6-[4-(4-cyanobenzyl)piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (1) addressed hERG and physical property issues, and led to clinical candidate 6-(4-(4-[2-(4-acetylpiperazin-1-yl)ethoxy]phenyl}piperidin-1-yl)-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine (12), designated AZD3514, that is being evaluated in a Phase I clinical trial in patients with castrate-resistant prostate cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.056

文献信息

• Discovery of AZD3514, a small-molecule androgen receptor downregulator for treatment of advanced prostate cancer
  作者：Robert H. Bradbury、David G. Acton、Nicola L. Broadbent、A. Nigel Brooks、Gregory R. Carr、Glenn Hatter、Barry R. Hayter、Kathryn J. Hill、Nicholas J. Howe、Rhys D.O. Jones、David Jude、Scott G. Lamont、Sarah A. Loddick、Heather L. McFarland、Zaieda Parveen、Alfred A. Rabow、Gorkhn Sharma-Singh、Natalie C. Stratton、Andrew G. Thomason、Dawn Trueman、Graeme E. Walker、Stuart L. Wells、Joanne Wilson、J. Matthew Wood

  DOI：10.1016/j.bmcl.2013.02.056

  日期：2013.4

  Removal of the basic piperazine nitrogen atom, introduction of a solubilising end group and partial reduction of the triazolopyridazine moiety in the previously-described lead androgen receptor downregulator 6-[4-(4-cyanobenzyl)piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (1) addressed hERG and physical property issues, and led to clinical candidate 6-(4-(4-[2-(4-acetylpiperazin-1-yl)ethoxy]phenyl}piperidin-1-yl)-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine (12), designated AZD3514, that is being evaluated in a Phase I clinical trial in patients with castrate-resistant prostate cancer. (C) 2013 Elsevier Ltd. All rights reserved.