4-(3-三氟甲氧基苯基)咪唑 | 684220-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(3-三氟甲氧基苯基)咪唑
• 英文名称: 4-(3-trifluoromethoxyphenyl)imidazole
• 英文别名: 4-(3-trifluoromethoxyphenyl)-1H-imidazole；5-[3-(trifluoromethoxy)phenyl]-1H-imidazole
• CAS: 684220-65-3
• 化学式: C₁₀H₇F₃N₂O
• 分子量: 228.174
• InChiKey: AGYJRJSUZJZFBS-UHFFFAOYSA-N

物化性质

• 沸点：
  345.1±37.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-三氟甲氧基苯基)咪唑 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-N-(3-ethoxypropyl)-4-methyl-2-(6-propyl-2-(4-(3-(trifluoromethoxy)phenyl)-1H-imidazol-1-yl)pyrimidin-4-ylamino)pentanamide
  参考文献：
  名称：

  Imidazolylpyrimidine based CXCR2 chemokine receptor antagonists

  摘要：

  An imidazolylpyrimidine was identified in a CXCR2 chemokine receptor antagonist screen and was optimized for potency, in vitro metabolic stability, and oral bioavailability. It was found that subtle structural modification within the series affected the oral bioavailability. Potent and orally available CXCR2 antagonists are herein reported. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.028
• 作为产物：
  描述：

  间三氟甲氧基-A-溴代苯乙酮 、 formamide 生成 4-(3-三氟甲氧基苯基)咪唑
  参考文献：
  名称：

  Imidazolylpyrimidine based CXCR2 chemokine receptor antagonists

  摘要：

  An imidazolylpyrimidine was identified in a CXCR2 chemokine receptor antagonist screen and was optimized for potency, in vitro metabolic stability, and oral bioavailability. It was found that subtle structural modification within the series affected the oral bioavailability. Potent and orally available CXCR2 antagonists are herein reported. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.028

文献信息

• Pyrimidine derivatives as IL-8 receptor antagonists
  申请人：——

  公开号：US20040087601A1

  公开（公告）日：2004-05-06

  Compounds containing the pyrimidine nucleus and their use to treat diseases and conditions related to inappropriate Interleukin-8 receptor activity are disclosed. The compounds are of the formula I 1 In these compounds, Q is preferably unsubstituted and substituted heterocyclyl; U is usually hydrogen or fluorine; and V is preferably hydrogen, halogen, alkyl, —O—alkyl or —S-alkyl. A representative example is: 2

  含有嘧啶核的化合物及其用于治疗与不适当的白细胞介素-8受体活性相关的疾病和症状的用途已被披露。这些化合物的结构式为I 1 在这些化合物中，Q最好是未取代或取代的杂环烷基；U通常是氢或氟；V最好是氢、卤素、烷基、—O—烷基或—S-烷基。一个代表性的例子是： 2
• [EN] (2S)-2-((PYRIMIDIN-4-YL)AMINO)-4-METHYLPENTANOIC ACID AMINOETHYLAMID DERIVATIVES AS IL-8 RECEPTOR MODULATORS FOR THE TREATMENT OF ATHEROSCLEROSIS AND RHEUMATOID ARTHRITIS<br/>[FR] DERIVES D'AMINOETHYLAMIDE D'ACIDE (2S)-2-((PYRIMIDIN-4-YL)AMINO)-4-METHYLPENTANOIQUE UTILISES COMME MODULATEURS DU RECEPTEUR DE L'IL-8 POUR TRAITER L'ATHEROSCLEROSE ET LA POLYARTHRITE RHUMATOIDE
  申请人：PHARMACOPEIA DRUG DISCOVERY

  公开号：WO2004069829A1

  公开（公告）日：2004-08-19

  The invention relates to compounds of the formula: (I); wherein R1 is a basic moiety having the structure -NH(CH2)2NR5R6, (Formula II) or (Formula II); wherein R5, R6 and R7 are independently selected from H, (1-6C)alkyl, (2-6C)alkenyl; (3-8C)cycloalkyl, and (1-6C)alkyl substituted with furanyl, (1-6C)alkoxy, (3-8C)cycloalkyl, trifluoromethyl or amido; or R5 and R6 together with N to which they are attached are a (4-8) membered heterocycle, which heterocycle may be substituted with (1-6C)alkoxy, trifluoromethyl or amido and which heterocycle may be fused with another (5-6) membered heterocycle; n is 1, 2 or 3; and the ring structure A represents a (4-6) membered heterocycle; R2 is (1-6C)alkyl, optionally substituted with (1-6C)alkoxy; R3 is aryl, heterocyclyl, -X-(CH2)maryl or -X-(CH2)m-heterocyclyl, wherein X is O, S or NR8, R8 being H or (1-6C)alkyl, and m is 0, 1, 2 or 3; and R4 is H, (1-8C)akyl, (1-8C)alkoxy or (2-8C)alkenyl, the alkyl moiety of each optionally being substituted with hydroxy, halogen, cyano, nitro, oxo, amino, alkylamino, dialkylamino, amido, alkylamido, carboxy, (1-8C)alkoxy, (1-8C)alkylthio, perfluoro (1-4C)alkyl, (3-8C)cycloalky, aryl, aryloxy, heterocyclyl or-0-heterocyclyl; or a pharmaceutically acceptable salt thereof. The compounds of the invention are Il-8 receptor modulators, in particular inhibitors thereof, and can be used for treating or preventing Il-8 receptor mediated disorders, such as atherosclerosis, inflammation, rheumatoid arthritis and related disorders.

  该发明涉及以下式的化合物：（I）；其中R1是具有结构-NH(CH2)2NR5R6的碱性基团，（式II）或（式II）；其中R5、R6和R7分别选自H、（1-6C）烷基、（2-6C）烯基；（3-8C）环烷基，以及用呋喃基、（1-6C）烷氧基、（3-8C）环烷基、三氟甲基或酰胺取代的（1-6C）烷基；或者R5和R6与它们连接的N一起是（4-8）成员杂环，该杂环可以用（1-6C）烷氧基、三氟甲基或酰胺取代，并且该杂环可以与另一个（5-6）成员杂环融合；n为1、2或3；环结构A代表（4-6）成员杂环；R2是（1-6C）烷基，可选地取代（1-6C）烷氧基；R3是芳基、杂环基、-X-(CH2)芳基或-X-(CH2)m-杂环基，其中X为O、S或NR8，R8为H或（1-6C）烷基，m为0、1、2或3；R4为H、（1-8C）烷基、（1-8C）烷氧基或（2-8C）烯基，每个烷基基团可选地取代羟基、卤素、氰基、硝基、氧代、氨基、烷基氨基、二烷基氨基、酰胺、烷基酰胺、羧基、（1-8C）烷氧基、（1-8C）烷基硫氧基、全氟（1-4C）烷基、（3-8C）环烷基、芳基、芳氧基、杂环基或-0-杂环基；或其药学上可接受的盐。该发明的化合物是Il-8受体调节剂，特别是其抑制剂，并可用于治疗或预防Il-8受体介导的疾病，如动脉粥样硬化、炎症、类风湿关节炎及相关疾病。
• US7037916B2
  申请人：——

  公开号：US7037916B2

  公开（公告）日：2006-05-02
• [EN] PYRIMIDINE DERIVATIVES AS IL-8 RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE PYRIMIDINE UTILISES COMME ANTAGONISTES DES RECEPTEURS DE L'IL-8
  申请人：PHARMACOPEIA INC

  公开号：WO2004062609A2

  公开（公告）日：2004-07-29

  Compounds containing the pyrimidine nucleus and their use to treat diseases and conditions related to inappropriate Interleukin-8 receptor activity are disclosed. The compounds are of the formula (I). In these compounds, Q is preferably unsubstituted and substituted heterocyclyl; U is usually hydrogen or fluorine; and V is preferably hydrogen, halogen, alkyl, -O-alkyl or -S-alkyl. A representative example is formula (X).
• Imidazolylpyrimidine based CXCR2 chemokine receptor antagonists
  作者：Koc-Kan Ho、Douglas S. Auld、Adolph C. Bohnstedt、Paolo Conti、Wim Dokter、Shawn Erickson、Daming Feng、Jim Inglese、Celia Kingsbury、Steven G. Kultgen、Rong-Qiang Liu、Christopher M. Masterson、Michael Ohlmeyer、Yajing Rong、Martijn Rooseboom、Andrew Roughton、Philippe Samama、Martin-Jan Smit、Ellen Son、Jaap van der Louw、Gerard Vogel、Maria Webb、Jac Wijkmans、Ming You

  DOI：10.1016/j.bmcl.2006.02.028

  日期：2006.5

  An imidazolylpyrimidine was identified in a CXCR2 chemokine receptor antagonist screen and was optimized for potency, in vitro metabolic stability, and oral bioavailability. It was found that subtle structural modification within the series affected the oral bioavailability. Potent and orally available CXCR2 antagonists are herein reported. (C) 2006 Elsevier Ltd. All rights reserved.