(E)-3-(4-chlorophenyl)-1-(4-(4-methylpiperazin-1-yl)phenyl)prop-2-en-1-one | 1260214-47-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-chlorophenyl)-1-(4-(4-methylpiperazin-1-yl)phenyl)prop-2-en-1-one
• 英文别名: 3-(4-Chlorophenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]prop-2-en-1-one；(E)-3-(4-chlorophenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]prop-2-en-1-one
• CAS: 1260214-47-8
• 化学式: C₂₀H₂₁ClN₂O
• 分子量: 340.853
• InChiKey: VFMYQKLMWCQWSP-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-chlorophenyl)-1-(4-(4-methylpiperazin-1-yl)phenyl)prop-2-en-1-one 、 三甲基碘化亚砜 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以84%的产率得到(2-(4-chlorophenyl)cyclopropyl)(4-(4-methylpiperazin-1-yl)phenyl)methanone
  参考文献：
  名称：

  Synthesis and bio-evaluation of alkylaminoaryl phenyl cyclopropyl methanones as antitubercular and antimalarial agents

  摘要：

  A series of 4-alkylaminoaryl phenyl cyclopropyl methanones (6a-6u and 8a-8c) were synthesized from 4-fluorochalcones (3a and 3b) by cyclopropanation of double bond followed by nucleophilic substitution of F with different amines. The compounds were screened for their antitubercular and antimalarial activities against Mycobacterium tuberculosis H37Rv and Plasmodium falciparum 3D7 strains in vitro respectively. Several compounds (6a, 6d-6h, 6p, 6q and 8a-8c) exhibited good in vitro antitubercular activities with MIC values 3.12-12.5 mu g/mL and preferentially inhibited the growth of P. falciparum in vitro (4a, 4c, 6a-6d, 6f, 6s, 8a and 8c) with IC50 as low as 0.080 and 0.035 mu g/mL and SI values 4975 and 6948, respectively. Molecular docking studies and in vitro evaluation against FAS-II enzymes using reporter gene assays were carried out to elucidate the mode of action of these molecules. Two compounds 4a and 6g showed significant inhibition at 25 mu M concentration of the compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.071
• 作为产物：
  描述：

  对氯苯乙酮 、 4-(4-甲基哌嗪)苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以51%的产率得到(E)-3-(4-chlorophenyl)-1-(4-(4-methylpiperazin-1-yl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design and Antiproliferative Activity of N-Heterocycle-Chalcone Derivatives

  摘要：

  研究人员制备了九种查尔酮衍生物，这些衍生物含有一个通过氮原子连接到其中一个苯环上的 N-杂环化合物，并评估了它们对肝癌、胃癌和神经内分泌癌细胞系的抗增殖活性。合成的大多数化合物对所有三种癌症细胞系都表现出中等至良好的活性，尤其是含有 4-（咪唑-1-基）苯基和 3,4,5- 三甲氧基苯基的查尔酮对肝癌细胞的抗增殖活性最高，IC50 值为 5.39 μM。

  DOI：

  10.3184/174751916x14740355883191

文献信息

• Design and Antiproliferative Activity of N-Heterocycle-Chalcone Derivatives
  作者：Dong-Jun Fu、Sai-Yang Zhang、Jian Song、Yin-Chao Liu、Li Zhang、Ruo-Han Zhao、Xiao-Lin Zi、Hong-Min Liu、Yan-Bing Zhang

  DOI：10.3184/174751916x14740355883191

  日期：2016.10

  Nine chalcone derivatives containing an N-heterocyclic compound attached by its nitrogen atom to one of the benzene rings were prepared and evaluated for their antiproliferative activity against liver, gastric and neuroendocrine cancer cell lines. Most of the synthesised compounds exhibited moderate to good activity against all three cancer cell lines, but in particular, a chalcone containing a 4-(imidazol-1-yl)phenyl group and a 3,4,5-trimethoxyphenyl group showed the highest antiproliferative activity with an IC₅₀ value of 5.39 μM against liver cancer cells.

  研究人员制备了九种查尔酮衍生物，这些衍生物含有一个通过氮原子连接到其中一个苯环上的 N-杂环化合物，并评估了它们对肝癌、胃癌和神经内分泌癌细胞系的抗增殖活性。合成的大多数化合物对所有三种癌症细胞系都表现出中等至良好的活性，尤其是含有 4-（咪唑-1-基）苯基和 3,4,5- 三甲氧基苯基的查尔酮对肝癌细胞的抗增殖活性最高，IC50 值为 5.39 μM。
• Synthesis and bio-evaluation of alkylaminoaryl phenyl cyclopropyl methanones as antitubercular and antimalarial agents
  作者：Arya Ajay、Vandana Singh、Shubhra Singh、Swaroop Pandey、Sarika Gunjan、Divya Dubey、Sudhir Kumar Sinha、Bhupendra N. Singh、Vinita Chaturvedi、Renu Tripathi、Ravishankar Ramchandran、Rama P. Tripathi

  DOI：10.1016/j.bmc.2010.09.071

  日期：2010.12

  A series of 4-alkylaminoaryl phenyl cyclopropyl methanones (6a-6u and 8a-8c) were synthesized from 4-fluorochalcones (3a and 3b) by cyclopropanation of double bond followed by nucleophilic substitution of F with different amines. The compounds were screened for their antitubercular and antimalarial activities against Mycobacterium tuberculosis H37Rv and Plasmodium falciparum 3D7 strains in vitro respectively. Several compounds (6a, 6d-6h, 6p, 6q and 8a-8c) exhibited good in vitro antitubercular activities with MIC values 3.12-12.5 mu g/mL and preferentially inhibited the growth of P. falciparum in vitro (4a, 4c, 6a-6d, 6f, 6s, 8a and 8c) with IC50 as low as 0.080 and 0.035 mu g/mL and SI values 4975 and 6948, respectively. Molecular docking studies and in vitro evaluation against FAS-II enzymes using reporter gene assays were carried out to elucidate the mode of action of these molecules. Two compounds 4a and 6g showed significant inhibition at 25 mu M concentration of the compound. (C) 2010 Elsevier Ltd. All rights reserved.