4-(3’-trifluoromethoxyphenoxy)benzonitrile | 1258834-98-8

• 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: 4-(3’-trifluoromethoxyphenoxy)benzonitrile
• 英文别名: 4-(3-(trifluoromethoxy)phenoxy)benzonitrile；4-(3-trifluoromethoxyphenoxy)benzonitrile；4-[3-(trifluoromethoxy)phenoxy]benzonitrile
• CAS: 1258834-98-8
• 化学式: C₁₄H₈F₃NO₂
• 分子量: 279.218
• InChiKey: NOLCMHCAXJIDTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3’-trifluoromethoxyphenoxy)benzonitrile 在 N-甲基吗啉 、 盐酸 、 lithium aluminium tetrahydride 、 三乙胺 、 silver(l) oxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 (R)-N-(4'-(3''-trifluoromethoxyphenoxy)benzyl)-2-acetamido-3-methoxypropionamide
  参考文献：
  名称：

  Chimeric derivatives of functionalized amino acids and α-aminoamides: Compounds with anticonvulsant activity in seizure models and inhibitory actions on central, peripheral, and cardiac isoforms of voltage-gated sodium channels

  摘要：

  Six novel 3 ''-substituted (R)-N-(phenoxybenzyl) 2-N-acetamido-3-methoxypropionamides were prepared and then assessed using whole-cell, patch-clamp electrophysiology for their anticonvulsant activities in animal seizure models and for their sodium channel activities. We found compounds with various substituents at the terminal aromatic ring that had excellent anticonvulsant activity. Of these compounds, (R)-N-4'-((3 ''-chloro) phenoxy) benzyl 2-N-acetamido-3-methoxypropionamide ((R)-5) and (R)-N-4'-((3 ''-trifluoromethoxy) phenoxy) benzyl 2-N-acetamido-3-methoxypropionamide ((R)-9) exhibited high protective indices (PI = TD50/ED50) comparable with many antiseizure drugs when tested in the maximal electroshock seizure test to mice (intraperitoneally) and rats (intraperitoneally, orally). Most compounds potently transitioned sodium channels to the slow-inactivated state when evaluated in rat embryonic cortical neurons. Treating HEK293 recombinant cells that expressed hNaV1.1, rNa(V)1.3, hNa(V)1.5, or hNa(V)1.7 with (R)-9 recapitulated the high levels of sodium channel slow inactivation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.014
• 作为产物：
  描述：

  3-三氟甲氧基苯酚 、 对氟苯腈 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以100%的产率得到4-(3’-trifluoromethoxyphenoxy)benzonitrile
  参考文献：
  名称：

  黄酮作为4（1 H）-喹诺酮类的等排体：发现有效的配体和双阶段抗疟铅化合物

  摘要：

  疟疾每年导致近一百万人死亡，恶性疟原虫的多抗性菌株的日益流行给控制该疾病带来了巨大挑战。制备了与4（1 H）-喹诺酮等排的多种黄酮，并对其抗恶性疟原虫W2菌株的血液阶段和鼠寄生虫伯氏疟原虫的肝脏阶段的抗疟原虫活性进行了分析。配体有效的潜在客户被确定为双阶段抗疟药，这表明支架优化可以提供有效的抗疟原虫化合物。

  DOI：

  10.1016/j.ejmech.2013.09.008

文献信息

• Flavones as isosteres of 4(1H)-quinolones: Discovery of ligand efficient and dual stage antimalarial lead compounds
  作者：Tiago Rodrigues、Ana S. Ressurreição、Filipa P. da Cruz、Inês S. Albuquerque、Jiri Gut、Marta P. Carrasco、Daniel Gonçalves、Rita C. Guedes、Daniel J.V.A. dos Santos、Maria M. Mota、Philip J. Rosenthal、Rui Moreira、Miguel Prudêncio、Francisca Lopes

  DOI：10.1016/j.ejmech.2013.09.008

  日期：2013.11

  diverse set of flavones, isosteric to 4(1H)-quinolones, were prepared and profiled for their antiplasmodial activity against the blood stage of P. falciparum W2 strain, and the liver stage of the rodent parasite Plasmodium berghei. Ligand efficient leads were identified as dual stage antimalarials, suggesting that scaffold optimization may afford potent antiplasmodial compounds.

  疟疾每年导致近一百万人死亡，恶性疟原虫的多抗性菌株的日益流行给控制该疾病带来了巨大挑战。制备了与4（1 H）-喹诺酮等排的多种黄酮，并对其抗恶性疟原虫W2菌株的血液阶段和鼠寄生虫伯氏疟原虫的肝脏阶段的抗疟原虫活性进行了分析。配体有效的潜在客户被确定为双阶段抗疟药，这表明支架优化可以提供有效的抗疟原虫化合物。
• COMPOSITION FOR AGRICULTURAL USE FOR CONTROLLING OR PREVENTING PLANT DISEASES CAUSED BY PLANT PATHOGENS
  申请人：Matsuzaki Yuichi

  公开号：US20110009454A1

  公开（公告）日：2011-01-13

  Disclosed is a composition for agricultural use, which is used for controlling or preventing plant diseases caused by plant pathogens. The composition for agricultural use contains a compound represented by formula (1), a salt thereof or a hydrate of the compound or the salt. (1) [In the formula, Z represents an oxygen atom, a sulfur atom or NR Z ; and E represents a furyl group, a thienyl group, a pyrrolyl group, a tetrazolyl group, a thiazolyl group, a pyrazolyl group, a phenyl group or the like.]

  本发明公开了一种用于农业用途的组合物，用于控制或预防由植物病原体引起的植物病害。该农业用组合物含有由式（1）表示的化合物，其盐或该化合物或盐的水合物。（1）[在该式中，Z代表氧原子、硫原子或NRZ；E代表呋喃基、噻吩基、吡咯基、四唑基、噻唑基、吡唑基、苯基或类似基团。]
• EP2248423
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] COMPOSITION FOR AGRICULTURAL USE FOR CONTROLLING OR PREVENTING PLANT DISEASES CAUSED BY PLANT PATHOGENS<br/>[FR] COMPOSITION À USAGE AGRICOLE POUR LUTTER CONTRE OU EMPÊCHER DES MALADIES DE PLANTE PROVOQUÉES PAR DES AGENTS PATHOGÈNES DE PLANTE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2009107764A1

  公开（公告）日：2009-09-03

  　植物病原菌による植物病害を防除又は予防するための、式（１）〔式中、Ｚは、酸素原子、硫黄原子またはＮＲＺを意味する；Ｅは、フリル基、チエニル基、ピロリル基、テトラゾリル基、チアゾリル基、ピラゾリル基またはフェニル基等を意味する〕で表される化合物もしくはその塩またはそれらの水和物を含有する農業用組成物等を提供する。
• Chimeric derivatives of functionalized amino acids and α-aminoamides: Compounds with anticonvulsant activity in seizure models and inhibitory actions on central, peripheral, and cardiac isoforms of voltage-gated sodium channels
  作者：Robert Torregrosa、Xiao-Fang Yang、Erik T. Dustrude、Theodore R. Cummins、Rajesh Khanna、Harold Kohn

  DOI：10.1016/j.bmc.2015.04.014

  日期：2015.7

  Six novel 3 ''-substituted (R)-N-(phenoxybenzyl) 2-N-acetamido-3-methoxypropionamides were prepared and then assessed using whole-cell, patch-clamp electrophysiology for their anticonvulsant activities in animal seizure models and for their sodium channel activities. We found compounds with various substituents at the terminal aromatic ring that had excellent anticonvulsant activity. Of these compounds, (R)-N-4'-((3 ''-chloro) phenoxy) benzyl 2-N-acetamido-3-methoxypropionamide ((R)-5) and (R)-N-4'-((3 ''-trifluoromethoxy) phenoxy) benzyl 2-N-acetamido-3-methoxypropionamide ((R)-9) exhibited high protective indices (PI = TD50/ED50) comparable with many antiseizure drugs when tested in the maximal electroshock seizure test to mice (intraperitoneally) and rats (intraperitoneally, orally). Most compounds potently transitioned sodium channels to the slow-inactivated state when evaluated in rat embryonic cortical neurons. Treating HEK293 recombinant cells that expressed hNaV1.1, rNa(V)1.3, hNa(V)1.5, or hNa(V)1.7 with (R)-9 recapitulated the high levels of sodium channel slow inactivation. (C) 2015 Elsevier Ltd. All rights reserved.