trans-2,4-dichloro-6-styrylpyrimidine

• 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: trans-2,4-dichloro-6-styrylpyrimidine
• 英文别名: (E)-2,4-dichloro-6-styrylpyrimidine；2,4-dichloro-6-[(E)-2-phenylethenyl]pyrimidine
• 化学式: C₁₂H₈Cl₂N₂
• 分子量: 251.115
• InChiKey: SYZFCAONBKAKMU-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2,4-dichloro-6-styrylpyrimidine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以52%的产率得到2,4-dichloro-6-ethylphenylpyrimidine
  参考文献：
  名称：

  Blocking Estrogen Signaling After the Hormone: Pyrimidine-Core Inhibitors of Estrogen Receptor-Coactivator Binding

  摘要：

  As an alternative approach to blocking estrogen action, we have developed small molecules that directly disrupt the key estrogen receptor (ER)/coactivator interaction necessary for gene activation. The more direct, protein-protein nature of this disruption might be effective even in hormone-refractory breast cancer. We have synthesized a pyrimidine-core library of moderate size, members of which act as a-helix mimics to block the ER alpha/coactivator interaction. Structure-activity relationships have been explored with various C-, N-, O-, and S-substituents on the pyrimidine core. Time-resolved fluorescence resonance energy transfer and cell-based reporter gene assays show that the most active members inhibit the ER alpha/steroid receptor coactivator interaction with Ki's in the low micromolar range. Through these studies, we have obtained a refined pharmacophore model for activity in this pyrimidine series. Furthermore, the favorable activities of several of these compounds support the feasibility that this coactivator binding inhibition mechanism for blocking estrogen action might provide a potential alternative approach to endocrine therapy.

  DOI：

  10.1021/jm800698b
• 作为产物：
  描述：

  反式-BETA-苯乙烯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 potassium hydrogen bifluoride 、 三乙胺 作用下， 以 乙醚 、 水 、 异丙醇 为溶剂， 反应 8.0h， 生成 trans-2,4-dichloro-6-styrylpyrimidine
  参考文献：
  名称：

  链烯基三氟硼酸钾的Suzuki-Miyaura交叉偶联反应。

  摘要：

  我们以前曾报道过，空气稳定的链烯基三氟硼酸钾与芳基卤化物和三氟甲磺酸酯的钯催化交叉偶联反应容易进行，收率很高。本文描述了概述此类反应的范围和局限性的最新进展。链烯基三氟硼酸钾与芳基和杂芳基卤化物和三氟甲磺酸酯的钯催化交叉偶联反应易于进行，产率中等至优异。烯基的交叉偶联反应通常可以在叔丁基NH 2作为碱的存在下，在i-PrOH-H 2 O中使用2mol％的PdCl 2（dppf）.CH 2 Cl 2作为催化剂来进行。两种配偶体均容忍多种官能团，并且该方法对于烯基三氟硼酸酯原料是立体定向的。

  DOI：

  10.1021/jo026236y

文献信息

• TETRA-ARYL CYCLOBUTANE INHIBITORS OF ANDROGEN RECEPTOR ACTION FOR THE TREATMENT OF HORMONE REFRACTORY CANCER
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20160229811A1

  公开（公告）日：2016-08-11

  The present disclosure provides tetra-substituted cyclobutane inhibitors of Androgen Receptor Action, and methods of using such inhibitors, for the treatment of hormone-refractory cancers.

  本公开提供了四取代环丁烷抑制剂的雄激素受体作用，并使用这些抑制剂的方法，用于治疗激素难治性癌症。
• [EN] TETRA-ARYL CYCLOBUTANE INHIBITORS OF ANDROGEN RECEPTOR ACTION FOR THE TREATMENT OF HORMONE REFRACTORY CANCER<br/>[FR] INHIBITEURS TÉTRA-ARYLE-CYCLOBUTANE DE L'ACTION DU RÉCEPTEUR DES ANDROGÈNES POUR LE TRAITEMENT D'UN CANCER RÉFRACTAIRE AUX HORMONES
  申请人：UNIV ILLINOIS

  公开号：WO2015048246A1

  公开（公告）日：2015-04-02

  The present disclosure provides tetra-substituted cyclobutane inhibitors of Androgen Receptor Action, and methods of using such inhibitors, for the treatment of hormone-refractory cancers.

  本公开提供了四取代环丁烷抑制剂，用于雄激素受体作用的抑制剂，并提供了使用这些抑制剂治疗激素难治性癌症的方法。
• π–π Interaction Energies as Determinants of the Photodimerization of Mono-, Di-, and Triazastilbenes
  作者：Alexander A. Parent、Daniel H. Ess、John A. Katzenellenbogen

  DOI：10.1021/jo500457n

  日期：2014.6.20

  We describe the quantitative [2 + 2] photo-cycloaddition of crystalline trans-2,4-dichloro-6-styrylpyrimidine to produce the corresponding htt r-ctt cyclobutane dimer, and we present H-1 NMR analysis of the photolysis of this and six other mono-, di-, and triazastilbenes in solid and solution states. Density functional (M06-2X) and correlated ab initio (MP2) calculations were used to obtain interaction energies I between two monomers of each azastilbene. These energies mirror the relative polarization of the stilbene moieties and can be quantitatively correlated with the rate of reaction and selective formation of the htt r-ctt dimers. In the solid state, poor correlation is observed between interaction energy and reactivity/selectivity. This lack of correlation is explained through X-ray analysis of the azastilbene monomers and is shown to be in accordance with the principles of Schmidt's topochemical postulate. Conversely, in solution there is a strong positive correlation (R-2 = 0.96) between interaction energies and formation of the htt rat dimer. These results are the first to show this correlation and to demonstrate the utility of calculated interaction energies as a tool for the prediction of stereo- and regioselectivity in solution-state stilbene-type photocycloadditions.
• [EN] DIAMINOPYRIMIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF<br/>[FR] DÉRIVÉS DE DIAMINOPYRIMIDINE ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：YUHAN CORP

  公开号：WO2012115479A3

  公开（公告）日：2012-11-01
• US9868705B2
  申请人：——

  公开号：US9868705B2

  公开（公告）日：2018-01-16