1-phenyl-1-[4-(trifluoromethyl)phenoxy]-3-(1H-imidazol-1-yl)propane | 745817-14-5

• 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: 1-phenyl-1-[4-(trifluoromethyl)phenoxy]-3-(1H-imidazol-1-yl)propane
• 英文别名: 1-(3-phenyl-3-(4-(trifluoromethyl)phenoxy)propyl)-1H-imidazole；1-[3-Phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]imidazole
• CAS: 745817-14-5
• 化学式: C₁₉H₁₇F₃N₂O
• 分子量: 346.352
• InChiKey: XXBMUFKLXRCIFB-UHFFFAOYSA-N

物化性质

• 沸点：
  495.3±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1-溴-3-氯丙基)苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 84.5h， 生成 1-phenyl-1-[4-(trifluoromethyl)phenoxy]-3-(1H-imidazol-1-yl)propane
  参考文献：
  名称：

  Imidazole Analogues of Fluoxetine, a Novel Class of Anti-Candida Agents

  摘要：

  Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-1-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH3 > NO2 > CF3).

  DOI：

  10.1021/jm049856v

文献信息

• Simplified Heterocyclic Analogues of Fluoxetine Inhibit Inducible Nitric Oxide Production in Lipopolysaccharide-Induced BV2 Cells
  作者：Ju-Young Park、Seung-Woo Kim、Ja-Kyeong Lee、Weon Bin Im、Byung Kwan Jin、Sung-Hwa Yoon

  DOI：10.1248/bpb.34.538

  日期：——

  A series of fluoxetine, where the N-methylamino group was replaced and then simplified, were synthesized and their inhibitory effect was tested for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in lipopolysaccharide (LPS)-induced BV2 cells. Although the synthesized compounds generally revealed weaker activity or greater cytotoxicity than fluoxetine, compound 10a, in which the N-methylamino group in fluoxetine was replaced by morpholine, and the trifluoromethylphenyl ring was substituted with simple oxo group, suppressed NO production dose-dependently at 10, 20 and 40 μM concentrations with less cytotoxicity than fluoxetine, and inhibited iNOS mRNA and protein expression at the same concentrations in LPS-induced BV2 cells. The results suggested that the trifluoromethylphenyl ring moiety in fluoxetine is not necessary for the suppression of NO production and that 10a has the potential as a potent inhibitor of NO production.

  合成了一系列氟西汀，替换并简化了N-甲基氨基团，并测试了它们对脂多糖（LPS）诱导的BV2细胞中一氧化氮（NO）产生和诱导性NO合酶（iNOS）表达的抑制作用。尽管合成的化合物一般显示出比氟西汀弱的活性或更大的细胞毒性，但化合物10a中氟西汀的N-甲基氨基团被莫尔夫啉替换，且三氟甲基苯环被简单的氧基取代，在10、20和40μM浓度下以剂量依赖的方式抑制了NO的产生，且其细胞毒性低于氟西汀，在同样浓度下抑制了LPS诱导的BV2细胞中的iNOS mRNA和蛋白表达。结果表明，氟西汀中的三氟甲基苯环结构对于抑制NO产生并不是必需的，且10a具备作为NO产生强效抑制剂的潜力。
• Synthesis of substituted aryloxy alkyl and aryloxy aryl alkyl imidazoles as antileishmanial agents
  作者：Kalpana Bhandari、Nagarapu Srinivas、Vijay K. Marrapu、Aditya Verma、Saumya Srivastava、Suman Gupta

  DOI：10.1016/j.bmcl.2009.10.117

  日期：2010.1

  A series of aryloxy alkyl/aryl alkyl imidazoles were synthesized and evaluated in vitro as antileishmanials against Leishmania donovani. All the 19 compounds exhibited 94–100% inhibition at 10 μg/mL against promastigotes and 12 compounds exhibited high inhibition with an IC50 in the range of 0.47–4.85 μg/mL against amastigotes. Promising compounds were tested further in vivo. Among all, compounds 4

  合成了一系列芳氧基烷基/芳基烷基咪唑，并作为抗利什曼原虫的体外抗疟药进行了体外评估。所有19种化合物在10μg/ mL的浓度下对前鞭毛体均表现出94-100％的抑制作用，而12种化合物在对amastigotes的IC 50为0.47-4.85μg/ mL时表现出高抑制性。有希望的化合物在体内进行了进一步测试。在所有化合物中，具有4-CF 3芳氧基部分的化合物4和23在体内对培养基的抑制作用为58–60％，从而为抗疟药提供了新的结构线索。
• Design and synthesis of 3-(azol-1-yl)phenylpropanes as microbicidal spermicides for prophylactic contraception
  作者：Lalit Kumar、Amit Sarswat、Nand Lal、Ashish Jain、Sumit Kumar、S.T.V.S. Kiran Kumar、Jagdamba P. Maikhuri、Atindra K. Pandey、Praveen K. Shukla、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.bmcl.2010.11.042

  日期：2011.1

  We designed a series of 25 3-(azol-1-yl)phenylpropanes which yielded 10 compounds (3, 4, 7, 8, 13, 14, 19, 21, 23, 26) that irreversibly immobilized 100% human sperm at 1% (w/v) concentration in 60 s; 12 compounds (8, 9, 15, 16, 19-21, 23-25, 27, 28) that showed potent microbicidal activity at 12.5-50 mu g/mL against Trichomonas vaginalis; and 17 compounds (3-11, 13, 15, 19, 21, 23, 26, 28, 30) that exhibited potent anticandida activity with minimum inhibitory concentration (MIC) of 12.5-50 mu g/mL. Almost all the compounds exhibited high level of safety towards normal vaginal flora (Lactobacillus) and human cervical (HeLa) cells in comparison to the marketed spermicide nonoxynol-9 (N-9). All the biological activities were evaluated in vitro. Two compounds (4, 8) with good safety profile exhibited multiple (spermicidal, antitrichomonas and anticandida) activities, warranting further lead optimization for furnishing a prophylactic vaginal contraceptive. (C) 2010 Elsevier Ltd. All rights reserved.