3-[4-(2-pyridyl)-piperazin-1-yl]-propionitrile | 743449-19-6

• 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: 3-[4-(2-pyridyl)-piperazin-1-yl]-propionitrile
• 英文别名: 3-(4-Pyridin-2-ylpiperazin-1-yl)propanenitrile
• CAS: 743449-19-6
• 化学式: C₁₂H₁₆N₄
• mdl: MFCD09939239
• 分子量: 216.286
• InChiKey: VUCLICRLNLGZIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[4-(2-pyridyl)-piperazin-1-yl]-propionitrile 在 sodium azide 、 三乙胺盐酸盐 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以87.4%的产率得到1-(2-pyridyl)-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
• 作为产物：
  描述：

  1-(2-吡啶基)哌嗪 、 丙烯腈 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以84.6%的产率得到3-[4-(2-pyridyl)-piperazin-1-yl]-propionitrile
  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

文献信息

• 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
  作者：Ram Shankar Upadhayaya、Neelima Sinha、Sanjay Jain、Nawal Kishore、Ramesh Chandra、Sudershan K. Arora

  DOI：10.1016/j.bmc.2004.02.014

  日期：2004.5

  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.