5-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-1H-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-1H-imidazole
• 英文别名: 5-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]-1H-imidazole
• 化学式: C₁₁H₆F₆N₂
• 分子量: 280.172
• InChiKey: DOHFQEAAPBKXOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-1H-imidazole 在 sodium hydroxide 作用下， 反应 2.0h， 以95%的产率得到2-(4-Trifluoromethyl-phenyl)-3H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  氟化咪唑作为19 F探针，用于仿生研究细胞色素c氧化酶中血红素a 3 -Cu b位点

  摘要：

  使用几种不同的方法修饰咪唑核心，从简单的可商购的氟化底物合成一系列带有氟化取代基的4,5-咪唑羧酸。这些咪唑衍生物经过专门设计，是用于使用19 F-NMR技术对金属配位环境中的过程进行物理化学研究的灵敏探针，特别是在我们正在进行的对咪唑衍生的卟啉的仿生研究中。

  DOI：

  10.1016/s0022-1139(00)00328-6
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 1,1,1-Trifluoro-3,3-dihydroxypropan-2-one 在 氨 作用下， 以 甲醇 、 水 为溶剂， 以83 %的产率得到5-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-1H-imidazole
  参考文献：
  名称：

  WO2024074414A1

  摘要：

  公开号：

文献信息

• [EN] 1,2-SUBSTITUTED IMIDAZOLYL COMPOUNDS FOR THE TREATMENT OF INFLAMMATION<br/>[FR] COMPOSES D'IMIDAZOLYLE SUBSTITUES EN POSITIONS 1 ET 2, CONVENANT AU TRAITEMENT DE L'INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：WO1996003388A1

  公开（公告）日：1996-02-08

  (EN) A class of imidazolyl compounds is described for use in treating inflammation. Compounds of particular interest are defined by formula (II), wherein R3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, acyl, cyano, alkoxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkyloxy, cycloalkyloxyalkyle, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cyanoalkyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, azidoalkyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, arylthio, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, aryloxy, heterocycloalkylcarbonyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonylalkyl, aralkylthio, heteroarylalcoxyalkyl, heteroaryloxyalkyl, aralkoxy, heteroarylthioalkyl, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl, wherein the aryl and heteroaryl radicals are optionally substitued at a substitutable position with one or more radicals selected from halo, alkylthio, alkylsufinyl, alkyl, cyano, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl and haloalkoxy; wherein R7 is a radical selected from alkyl and amino; and wherein R8 is one or more radicals selected from hydrido, halo, alkyl, haloalkyl, alkoxy, amino, haloalkoxy, cyano, carboxyl, hydroxyl, hydroxyalkyl, alkoxyalkyl, alkylamino, nitro and alkylthio.(FR) La présente invention concerne une classe de composés d'imidazolyle convenant au traitement de l'inflammation. Les composés concernés en l'occurrence sont décrits par la formule générale (II). Dans cette formule générale (II), 'R3' représente un radical choisi parmi hydrido, alkyle, haloalkyle, aralkyle, hétérocycloalkyle, acyle, cyano, alcoxy, alkylthio, alkylthioalkyle, alkylsulfonyle, cycloalkyloxy, cycloalkyloxyalkyle, cycloalkylthio, cycloalkylthioalkyle, cycloalkylsulfonyle, cyanoalkyle, cycloalkylsulfonylalkyle, haloalkylsulfonyle, azidoalkyle, arylsulfonyle, halo, hydroxyalkyle, alcoxyalkyle, arylthio, alkylcarbonyle, arylcarbonyle, aralkylcarbonyle, aryloxy, hétérocycloalkylcarbonyle, alkylaminoalkyle, N-arylaminoalkyle, N-alkyl-N-arylaminoalkyle, carboxyalkyle, alcoxycarbonylalkyle, alcoxycarbonyle, haloalkylcarbonyle, aminocarbonyle, alkylaminocarbonylalkyle, aralkylthio, hétéroarylalcoxyalkyle, hétéroaryloxyalkyle, aralcoxy, hétéroarylthioalkyle, hétéroaralcoxy, hétéroaralkylthio, hétéroarylalkylthioalkyle, hétéroaryloxy, hétéroarylthio, arylthioalkyle, aryloxyalkyle, aralkylthioalkyle, aralcoxyalkyle, aryle et hétéroaryle, les radicaux aryle et hétéroaryle étant éventuellement substitués à des positions admettant la substitution par au moins un radical choisi parmi halo, alkylthio, alkylsulfinyle, alkyle, cyano, haloalkyle, hydroxyle, alcoxyle, hydroxyalkyle et haloalcoxy. 'R7' représente un radical choisi parmi alkyle et amino. 'R8' représente au moins un radical choisi parmi hydrido, halo, alkyle, haloalkyle, alcoxy, amino, haloalcoxy, cyano, carboxyle, hydroxyle, hydroxyalkyle, alcoxyalkyle, alkylamino, nitro et alkylthio.

  描述了一类咪唑基化合物，用于治疗炎症。特别感兴趣的化合物由式(II)表示，其中R3为选自氢、烷基、卤代烷基、芳烷基、杂环烷基、酰基、氰基、烷氧基、烷硫基、烷硫基烷基、烷基磺酰基、环烷氧基、环烷氧基烷基、环烷硫基、环烷硫基烷基、环烷基磺酰基、氰基烷基、环烷基磺酰基烷基、卤代烷基磺酰基、硝基烷基、芳基磺酰基、卤素、羟基烷基、烷氧基烷基、芳硫基、烷基羰基、芳基羰基、芳烷基羰基、 aryloxy、杂环烷基羰基、烷基氨基烷基、N-芳基氨基烷基、N-烷基-N-芳基氨基烷基、羧基烷基、烷氧羰基烷基、烷氧羰基、卤代烷基羰基、氨基羰基、烷基氨基羰基烷基、芳烷硫基、杂环烷基羰基烷基、杂芳基氧基烷基、杂芳氧基烷基、芳烷氧基、杂芳基硫代烷基、杂芳烷氧基、杂芳烷硫基、杂芳基烷硫基烷基、杂芳氧基、杂芳基硫基、芳基硫代烷基、芳氧基烷基、芳烷硫基烷基、芳烷氧基烷基、芳基和杂芳基的基团，其中所述芳基和杂芳基基团在可取代的位置上任选地被一个或多个卤素、烷基硫基、烷基磺酰基、烷基、氰基、卤代烷基、羟基、烷氧基、羟基烷基和卤代烷氧基取代；其中R7为选自烷基和氨基的基团；并且R8为一个或多个选自氢、卤素、烷基、卤代烷基、烷氧基、氨基、卤代烷氧基、氰基、羧基、羟基、羟基烷基、烷氧基烷基、烷基氨基、硝基和烷基硫基的基团。
• Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones
  作者：Alain Dhainaut、André Tizot、Eric Raimbaud、Brian Lockhart、Pierre Lestage、Solo Goldstein

  DOI：10.1021/jm991154w

  日期：2000.6.1

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.
• 1,2-SUBSTITUTED IMIDAZOLYL COMPOUNDS FOR THE TREATMENT OF INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：EP0772600A1

  公开（公告）日：1997-05-14
• Fluorinated imidazoles as 19F probes for biomimetic studies of heme a3 — Cub site in cytochrome c oxidase
  作者：James P. Collman、Roman Boulatov、Christopher J. Sunderland、Min Zhong

  DOI：10.1016/s0022-1139(00)00328-6

  日期：2000.12

  A series of 4,5-imidazole carboxylic acids bearing fluorinated substituents is synthesized from simple commercially available fluorinated substrates utilizing several different approaches to modify the imidazole core. These imidazole derivatives are specifically designed to be sensitive probes for physicochemical studies of processes in the coordination environments of metals employing 19F-NMR techniques

  使用几种不同的方法修饰咪唑核心，从简单的可商购的氟化底物合成一系列带有氟化取代基的4,5-咪唑羧酸。这些咪唑衍生物经过专门设计，是用于使用19 F-NMR技术对金属配位环境中的过程进行物理化学研究的灵敏探针，特别是在我们正在进行的对咪唑衍生的卟啉的仿生研究中。
• WO2024074414A1
  申请人：——

  公开号：——

  公开（公告）日：——