2-chloro-1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethanone | 802009-62-7

• 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: 2-chloro-1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethanone
• 英文别名: 2-chloro-1-(4-((4-chlorophenyl)phenylmethyl)piperazin-1-yl)ethan-1-one；2-Chloro-1-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethan-1-one；2-chloro-1-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethanone
• CAS: 802009-62-7
• 化学式: C₁₉H₂₀Cl₂N₂O
• 分子量: 363.287
• InChiKey: LIYHXSPBTDRCRV-UHFFFAOYSA-N

物化性质

• 沸点：
  489.7±45.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethanone 、 2-甲基-4-硝基咪唑 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以53%的产率得到1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-(2-methyl-4-nitro-1H-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
• 作为产物：
  描述：

  1-(4-氯二苯甲基)哌嗪 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以45%的产率得到2-chloro-1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-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

• 3-Nitrotriazole-based piperazides as potent antitrypanosomal agents
  作者：Maria V. Papadopoulou、William D. Bloomer、Howard S. Rosenzweig、Ivan P. O'Shea、Shane R. Wilkinson、Marcel Kaiser

  DOI：10.1016/j.ejmech.2015.08.042

  日期：2015.10

  Novel linear 3-nitro-1H-1,2,4-triazole-based piperazides were synthesized and evaluated as anti-trypanosomal agents. In addition, some bisarylpiperazine-ethanones which were formed as by-products were also screened for antiparasitic activity. Most 3-nitrotriazole-based derivatives were potent and selective against Trypanosoma cruzi parasites, but only one displayed these desired properties against Trypanosoma brucei rhodesiense. Moreover, two 3-nitrotriazole-based chlorophenylpiperazides were moderately and selectively active against Leishmania donovani. Although the bisarylpiperazineethanones were active or moderately active against I cruzi, none of them demonstrated an acceptable selectivity. In general, 3-nitrotriazole-based piperazides were less toxic to host L6 cells than the previously evaluated 3-nitrotriazole-based piperazines and seven of 13 were 1.54- to 31.2-fold more potent antichagasic agents than the reference drug benznidazole. Selected compounds showed good ADMET characteristics. One potent in vitro antichagasic compound (3) was tested in an acute murine model and demonstrated antichagasic activity after a 10-day treatment of 15 mg/kg/day. However, neither compound 3 nor benznidazole showed a statistically significant P value compared to control due to high variability in parasite burden among the untreated animals. Working as prodrugs, 3-nitrotriazole-based piperazides were excellent substrates of trypanosomal type I nitroreductases and constitute a novel class of potentially effective and more affordable antitrypanosomal agents. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis, antiproliferative, antioxidant activities, in silico studies, DFT analysis and molecular dynamics simulation of novel 1-(4-chlorobenzhydryl) piperazine derivatives
  作者：Najim A. Al-Masoudi、Raad S. Jihad、Nabeel A. Abdul-Rida、Amer M.J. Al-Shamari、Bahjat A. Saeed、Wasfi A. Al-Masoudi、Amneh Shtaiwi、Yaseen A. Al-Soud

  DOI：10.1016/j.molstruc.2023.137028

  日期：2024.2