3-[4-(4-fluorophenyl)-piperazin-1-yl]-propionitrile | 169877-37-6

• 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-(4-fluorophenyl)-piperazin-1-yl]-propionitrile
• 英文别名: 3-[4-(4-fluorophenyl)piperazin-1-yl]propanenitrile
• CAS: 169877-37-6
• 化学式: C₁₃H₁₆FN₃
• mdl: MFCD03237143
• 分子量: 233.289
• InChiKey: BRVUCSKROBTQJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[4-(4-fluorophenyl)-piperazin-1-yl]-propionitrile 在 sodium azide 、 三乙胺盐酸盐 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 58.0h， 生成 (2R,3S)-2-(2,4-difluorophenyl)-3-[5-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl]tetrazol-1-yl]-1-(1,2,4-triazol-1-yl)butan-2-ol
  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：

  3-溴丙腈 、 1-(4-氟苯基)哌嗪 在 cesium hydroxide 、 sodium iodide 作用下， 反应 0.33h， 以88%的产率得到3-[4-(4-fluorophenyl)-piperazin-1-yl]-propionitrile
  参考文献：
  名称：

  Solventless microwave assisted protocol for synthesis of arylalkylpiperazines using Cs-base

  摘要：

  在干燥介质条件下，利用CsOH在微波辐射下制备了一系列取代芳基烷基哌嗪，获得了较高的产率，并且具有良好的化学选择性和区域选择性。

  DOI：

  10.1039/b812801d

文献信息

• Substituted cyclic amine compounds as 5HT2 antagonists
  申请人：TOA EIYO LTD.

  公开号：EP0661266A1

  公开（公告）日：1995-07-05

  A substituted cyclic amine compound represented by the following general formula (1) wherein each of R¹ to R⁵ represents a hydrogen atom, a hydroxyl group, an alkyl group or the like, D represents a methine moiety, a nitrogen atom or the like, P represents -CR⁶(R⁷)- or -NR⁸-, Q represents a methine moiety or a nitrogen atom, each of T and B is a single bond or represents a methylene moiety, a carbonyl group or the like, n is an integer of 1 to 6 and each of R⁶, R⁷ and R⁸ represents a hydrogen atom, an alkyl group or the like; and synthetic intermediates thereof. The inventive compound is useful in preventing and treating circulatory organ-related diseases such as hypertension, ischemic heart disease, cerebrovascular disease, peripherol circulatory disease and the like.

  由以下通式（1）代表的取代环胺化合物 其中 R¹ 至 R⁵ 各代表氢原子、羟基、烷基或类似物，D 代表甲基、氮原子或类似物，P 代表-CR⁶(R⁷)- 或-NR⁸-，Q 代表甲基或氮原子、T和B各自为单键或代表亚甲基、羰基或类似基团，n为1至6的整数，R⁶、R⁷和R⁸各自代表氢原子、烷基或类似基团；及其合成中间体。 本发明化合物可用于预防和治疗循环器官相关疾病，如高血压、缺血性心脏病、脑血管疾病、外周循环疾病等。
• 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.
• Solventless microwave assisted protocol for synthesis of arylalkylpiperazines using Cs-base
  作者：Alain Gamal Giuglio-Tonolo、Thierry Terme、Patrice Vanelle

  DOI：10.1039/b812801d

  日期：——

  A series of some arylalkylpiperazines was prepared in good yields under microwave irradiation in dry media conditions using CsOH with high chemo- and regioselectivity.

  在干燥介质条件下，利用CsOH在微波辐射下制备了一系列取代芳基烷基哌嗪，获得了较高的产率，并且具有良好的化学选择性和区域选择性。