Tert-butyl 4-(4-{[3-(4-chlorophenyl)propyl]sulfanyl}-6-{[2-(4-hydroxyphenyl)ethyl]amino}-1,3,5-triazin-2-yl)-1-piperazinecarboxylate | 459872-71-0

• 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: Tert-butyl 4-(4-{[3-(4-chlorophenyl)propyl]sulfanyl}-6-{[2-(4-hydroxyphenyl)ethyl]amino}-1,3,5-triazin-2-yl)-1-piperazinecarboxylate
• 英文别名: tert-butyl 4-[4-[3-(4-chlorophenyl)propylsulfanyl]-6-[2-(4-hydroxyphenyl)ethylamino]-1,3,5-triazin-2-yl]piperazine-1-carboxylate
• CAS: 459872-71-0
• 化学式: C₂₉H₃₇ClN₆O₃S
• 分子量: 585.17
• InChiKey: AMVAJOOKUGKPIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-(4-{[3-(4-chlorophenyl)propyl]sulfanyl}-6-{[2-(4-hydroxyphenyl)ethyl]amino}-1,3,5-triazin-2-yl)-1-piperazinecarboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以0.47 g的产率得到4-(2-{[4-{[3-(4-chlorophenyl)-propyl]sulfanyl}-6-(1-piperazinyl)-1,3,5-triazin-2-yl]amino}ethyl)-phenol
  参考文献：
  名称：

  A New Series of Estrogen Receptor Modulators That Display Selectivity for Estrogen Receptor β

  摘要：

  A series of 1,3,5-triazine-based estrogen receptor (ER) modulators that are modestly selective for the ERbeta subtype are reported. Compound 1, which displayed modest potency and selectivity for ERbeta vs ERalpha, was identified via high-throughput screening utilizing an ERbeta SPA-based binding assay. Subsequent analogue preparation resulted in the identification of compounds such as 21 and 43 that display 25- to 30-fold selectivity for ERbeta with potencies in the 10-30 nM range. These compounds profile as full antagonists at ERbeta and weak partial agonists at ERalpha in a cell-based reporter gene assay. In addition, the X-ray crystal structure of compound 15 complexed with the ligand binding domain of ERbeta has been solved and was utilized in the design of more conformationally restrained analogues such as 31 in an attempt to increase selectivity for the ERbeta subtype.

  DOI：

  10.1021/jm020291h
• 作为产物：
  描述：

  3-(4-氯苯基)丙酸 在 sodium hydroxide 、 硼烷 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Tert-butyl 4-(4-{[3-(4-chlorophenyl)propyl]sulfanyl}-6-{[2-(4-hydroxyphenyl)ethyl]amino}-1,3,5-triazin-2-yl)-1-piperazinecarboxylate
  参考文献：
  名称：

  A New Series of Estrogen Receptor Modulators That Display Selectivity for Estrogen Receptor β

  摘要：

  A series of 1,3,5-triazine-based estrogen receptor (ER) modulators that are modestly selective for the ERbeta subtype are reported. Compound 1, which displayed modest potency and selectivity for ERbeta vs ERalpha, was identified via high-throughput screening utilizing an ERbeta SPA-based binding assay. Subsequent analogue preparation resulted in the identification of compounds such as 21 and 43 that display 25- to 30-fold selectivity for ERbeta with potencies in the 10-30 nM range. These compounds profile as full antagonists at ERbeta and weak partial agonists at ERalpha in a cell-based reporter gene assay. In addition, the X-ray crystal structure of compound 15 complexed with the ligand binding domain of ERbeta has been solved and was utilized in the design of more conformationally restrained analogues such as 31 in an attempt to increase selectivity for the ERbeta subtype.

  DOI：

  10.1021/jm020291h

文献信息

• Piperazinyltriazines as estrogen receptor modulators
  申请人：——

  公开号：US20040072829A1

  公开（公告）日：2004-04-15

  Triazine derivatives of formula (I), which exhibit pharmacological activity at estrogen receptors alpha (ER alpha) and beta (ER beta) are described herein. The described invention also includes compositions and medicaments containing the triazine derivatives as well as processes for the preparation and use of such compounds, compositions and medicaments. 1

  本文描述了式(I)的三嗪衍生物，其在雌激素受体α（ERα）和β（ERβ）上表现出药理活性。所述发明还包括含有三嗪衍生物的组合物和药物，以及制备和使用这种化合物、组合物和药物的方法。
• US6943162B2
  申请人：——

  公开号：US6943162B2

  公开（公告）日：2005-09-13
• [EN] PIPERAZINYLTRIAZINES AS ESTROGEN RECEPTOR MODULATORS<br/>[FR] PIPERAZINYLTRIAZINES EN TANT QUE MODULATEURS DE RECEPTEURS D'OESTROGENES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2002072561A1

  公开（公告）日：2002-09-19

  Triazine derivatives of formula (I), which exhibit pharmacological activity at estrogen receptors alpha (ER alpha) and beta (ER beta) are described herein. The described invention also includes compositions and medicaments containing the triazine derivatives as well as processes for the preparation and use of such compounds, compositions and medicaments.