1-(3-trifluoromethylphenyl)-4-[2-(1H-tetrazol-5-yl)-ethyl]-piperazine | 4004-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(3-trifluoromethylphenyl)-4-[2-(1H-tetrazol-5-yl)-ethyl]-piperazine
• 英文别名: 1-[2-(2H-tetrazol-5-yl)ethyl]-4-[3-(trifluoromethyl)phenyl]piperazine
• CAS: 4004-92-6
• 化学式: C₁₄H₁₇F₃N₆
• 分子量: 326.324
• InChiKey: YEBWNBCBGMUKPU-UHFFFAOYSA-N

物化性质

• 沸点：
  480.2±55.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(3-trifluoromethylphenyl)-4-[2-(1H-tetrazol-5-yl)-ethyl]-piperazine 在 sodium hydride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-3-(5-{2-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-ethyl}-tetrazol-1-yl)-butan-2-ol
  参考文献：
  名称：

  Synthesis of novel substituted tetrazoles having antifungal activity

  摘要：

  In an effort to find potent antifungal agents, a variety of triazole derivatives with a 5-substituted tetrazole structure 6, 7, 12 and 14 were prepared and evaluated for antifungal activity against Candida spp., Cryptococcus neoformans, and Aspergilhis spp. in vitro. The location of the methyl group at the C-3 of compounds 12 and 14 has been demonstrated to be a key structural element of antifungal potency. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.03.004
• 作为产物：
  描述：

  3-[4-(3-(trifluoromethyl)phenyl)piperazin-1-yl]propanenitrile 在 sodium azide 、 三乙胺盐酸盐 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以89.2%的产率得到1-(3-trifluoromethylphenyl)-4-[2-(1H-tetrazol-5-yl)-ethyl]-piperazine
  参考文献：
  名称：

  Optically active antifungal azoles: synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol

  摘要：

  A series of (2 R, 3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazo-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yi]-ethyl}-tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl ring of piperazine demonstrated significant antifungal activity against variety of fungal cultures (Candida spp. C. neoformans and Aspergillus spp.). The compound 12d showed MIC value of 0.12mug/mL for C. albicans, C albicans V-01-191A-261 (resistant strain); 0.25mug/mL for C tropicalis, C parapsilosis ATCC 22019 and C krusei and MIC value of 0.5 mug/mL for C glabrata, C krusei ATCC 6258, which is comparable to itraconazole and better than fluconazole. Further, compound 11d showed significant activity (MIC; 0.25-0.5 mug/mL) against Candida spp. and strong anticryptococcal activity (MIC; 0.25 mug/mL) against C neoformans. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.014