4-chloro-2-phenyl-6-trifluoromethylpyrimidine | 184109-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-chloro-2-phenyl-6-trifluoromethylpyrimidine
• 英文别名: 4-Chloro-2-phenyl-6-(trifluoromethyl)pyrimidine
• CAS: 184109-83-9
• 化学式: C₁₁H₆ClF₃N₂
• mdl: MFCD00559594
• 分子量: 258.63
• InChiKey: CWZUWJRMFIDBRA-UHFFFAOYSA-N

物化性质

• 沸点：
  215.7±40.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-2-phenyl-6-trifluoromethylpyrimidine 在 sodium azide 、 lithium chloride 作用下， 以 氘代二甲亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4-azido-6-(trifluoromethyl)-2-phenylpyrimidine
  参考文献：
  名称：

  2,6-二取代 4-叠氮嘧啶：通过核磁共振光谱法对叠氮四唑重排的合成、动力学和热力学研究

  摘要：

  通过 NOESY/EXSY 和 DNMR 确定一系列 2,6-二取代 4-叠氮嘧啶的互变异构四唑-叠氮重排的热力学和动力学参数：ΔH = 15-28 kJ mol-1；ΔS = 47—65 J mol–1 К–1；Еa = 93—117 kJ mol–1；lgA = 15.1—18.9。它们取决于取代基的电子特性和溶剂的极性。

  DOI：

  10.1007/s11172-017-1986-2
• 作为产物：
  描述：

  2-phenyl-6-(trifluoromethyl)pyrimidin-4-ol 在 N,N-二甲基甲酰胺 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 4-chloro-2-phenyl-6-trifluoromethylpyrimidine
  参考文献：
  名称：

  [EN] PYRIMIDINE COMPOUND AND ITS USE IN PEST CONTROL
  [FR] COMPOSÉ PYRIMIDINE ET SON UTILISATION DANS LA LUTTE ANTIPARASITAIRE

  摘要：

  以下公式（I）所代表的嘧啶化合物对害虫具有出色的控制活性，并可用作杀虫剂的活性成分。

  公开号：

  WO2010134478A1

文献信息

• Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators or caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US20030069239A1

  公开（公告）日：2003-04-10

  The present invention is directed to substituted 2-aryl-4-arylaminopyrimidine and analogs thereof, represented by the general Formula I: 1 wherein A, Ar 1 , Ar 2 , R 1 and R 3 are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. The compounds of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被一般式I所代表的取代的2-芳基-4-芳基氨基嘧啶及其类似物： 其中A，Ar1，Ar2，R1和R3在此处被定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。本发明的化合物可用于诱导在出现未受控制的异常细胞生长和扩散的各种临床病况中的细胞死亡。
• Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US20040097503A1

  公开（公告）日：2004-05-20

  The present invention is directed to substituted 2-aryl-4-arylaminopyrimidine and analogs thereof, represented by the general Formula I: 1 wherein A, Ar 1 , Ar 2 , R 1 and R 3 are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. The compounds of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的2-芳基-4-芳氨基嘧啶及其类似物，由通式I表示：其中A、Ar1、Ar2、R1和R3如本文所定义。本发明还涉及发现具有I式化合物的活化剂和凋亡诱导剂。本发明的化合物可用于在各种临床情况下诱导细胞死亡，其中出现了不受控制的异常细胞的生长和扩散。
• Discovery of substituted 4-anilino-2-arylpyrimidines as a new series of apoptosis inducers using a cell- and caspase-based high throughput screening assay. 2. Structure–activity relationships of the 2-aryl group
  作者：Nilantha Sirisoma、Azra Pervin、Bao Nguyen、Candace Crogan-Grundy、Shailaja Kasibhatla、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2009.02.074

  日期：2009.4

  As a continuation of our efforts to discover and develop the apoptosis inducing 4-anilino-2-(2-pyridyl) pyrimidines as potential anticancer agents, we explored replacing the 2-pyridyl group by other aryl groups. SAR studies showed that the 2-pyridyl group can be replaced by a 3-pyridyl, 4-pyridyl and 2-pyrazinyl group, and that the SAR for the anilino group was similar to that of the 2-pyridyl series. However, replacement of the 2-pyridyl group by a phenyl group, a 3,5-dichloro-4-pyridyl group, or a saturated ring led to inactive compounds. Several potent compounds, including 2f, 3d, 3j and 4a, with EC50 values of 0.048-0.024 mu M in the apoptosis induction assay against T47D cells, were identified through the SAR studies. In a tubulin polymerization assay, compound 2f, which was active against all the three cell lines tested (T47D, HTC116 and SNU398), inhibited tubulin polymerization with an IC50 value of 0.5 mu M, while compound 2a, which was active against T47D cells but not active against HTC116 and SNU398 cells, was not active in the tubulin assay at up to 50 mu M. (c) 2009 Elsevier Ltd. All rights reserved.
• ACETAMIDE DERIVATIVES, PROCESS FOR PRODUCING THE SAME, AND MEDICINAL COMPOSITION CONTAINING THE SAME
  申请人：DAINIPPON PHARMACEUTICAL CO., LTD.

  公开号：EP0826673B1

  公开（公告）日：2002-11-20
• EP1351691A4
  申请人：——

  公开号：EP1351691A4

  公开（公告）日：2005-06-22