1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanone | 1275578-49-8

• 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-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanone
• 英文别名: 1-[4-[(4-Chlorophenyl)-phenyl-methyl]piperazin-1-yl]-2-(5,6-dimethylbenzimidazol-1-yl)ethanone；1-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]-2-(5,6-dimethylbenzimidazol-1-yl)ethanone
• CAS: 1275578-49-8
• 化学式: C₂₈H₂₉ClN₄O
• 分子量: 473.017
• InChiKey: JUIPWLLELOVPJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-氯二苯甲基)哌嗪 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis of Azole-containing Piperazine Derivatives and Evaluation of their Antibacterial, Antifungal and Cytotoxic Activities

  摘要：

  设计并合成了一系列含有三唑环的哌嗪衍生物。所得化合物在体外进行了抗菌、抗真菌和细胞毒性活性的研究。初步结果表明，大多数化合物在体外表现出中等到显著的抗菌和抗真菌活性。1-(4-((4-氯苯基)(苯基)甲基)哌嗪-1-基)-2-(1H-咪唑-1-基)乙酮和1-(4-((4-氯苯基)(苯基)甲基)哌嗪-1-基)-2-(2-苯基-1H-咪唑-1-基)乙酮对所有测试菌株显示出显著且广谱的抗微生物效力，MIC值范围为3.1至$25\;{\mu}g/mL$，并显示出与临床标准药物氯霉素和氟康唑相当的活性。此外，2-((4-((4-氯苯基)(苯基)甲基)哌嗪-1-基)甲基)-1H-苯并[d]咪唑在体外对PC-3细胞系最为有效，其生长抑制值（分别为36.4%、60.1%和76.5%）按剂量依赖方式对应于$25\;{\mu}g/mL$、$50\;{\mu}g/mL$和$100\;{\mu}g/mL$的测试浓度。结果还显示，三唑环对其抗微生物和细胞毒性活性有明显影响，咪唑和苯并咪唑部分比1,2,4-三唑更有利于生物活性。

  DOI：

  10.5012/bkcs.2010.31.12.3684

文献信息

• Synthesis of Azole-containing Piperazine Derivatives and Evaluation of their Antibacterial, Antifungal and Cytotoxic Activities
  作者：Lin-Ling Gan、Bo Fang、Cheng-He Zhou

  DOI：10.5012/bkcs.2010.31.12.3684

  日期：2010.12.20

  A series of azole-containing piperazine derivatives have been designed and synthesized. The obtained compounds were investigated in vitro for their antibacterial, antifungal and cytotoxic activities. The preliminary results showed that most compounds exhibited moderate to significant antibacterial and antifungal activities in vitro. 1-(4-((4-chlorophenyl) (phenyl)methyl)piperazin-1-yl)-2-(1H-imidazol-1-yl)ethanone and 1-(4-((4-Chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-(2-phenyl-1H-imidazol-1-yl)ethanone gave remarkable and broad-spectrum antimicrobial efficacy against all tested strains with MIC values ranging from 3.1 to $25\;\mu}g/mL$, and exhibited comparable activities to the standard drugs chloramphenicol and fluconazole in clinic. Moreover, 2-((4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)methyl)-1H-benzo[d]imidazole was found to be the most effective in vitro against the PC-3 cell line, reaching growth inhibition values (36.4, 60.1 and 76.5%) for each tested concentration: $25\;\mu}g/mL$, $50\;\mu}g/mL$ and $100\;\mu}g/mL$ in dose-dependent manner. The results also showed that the azole ring had noticeable effect on their antimicrobial and cytotoxic activities, and imidazole and benzimidazole moiety were much more favourable to biological activity than 1,2,4-triazole.

  设计并合成了一系列含有三唑环的哌嗪衍生物。所得化合物在体外进行了抗菌、抗真菌和细胞毒性活性的研究。初步结果表明，大多数化合物在体外表现出中等到显著的抗菌和抗真菌活性。1-(4-((4-氯苯基)(苯基)甲基)哌嗪-1-基)-2-(1H-咪唑-1-基)乙酮和1-(4-((4-氯苯基)(苯基)甲基)哌嗪-1-基)-2-(2-苯基-1H-咪唑-1-基)乙酮对所有测试菌株显示出显著且广谱的抗微生物效力，MIC值范围为3.1至$25\;\mu}g/mL$，并显示出与临床标准药物氯霉素和氟康唑相当的活性。此外，2-((4-((4-氯苯基)(苯基)甲基)哌嗪-1-基)甲基)-1H-苯并[d]咪唑在体外对PC-3细胞系最为有效，其生长抑制值（分别为36.4%、60.1%和76.5%）按剂量依赖方式对应于$25\;\mu}g/mL$、$50\;\mu}g/mL$和$100\;\mu}g/mL$的测试浓度。结果还显示，三唑环对其抗微生物和细胞毒性活性有明显影响，咪唑和苯并咪唑部分比1,2,4-三唑更有利于生物活性。