(2E,4E)-1-(4-aminophenyl)-5-phenylpenta-2,4-dien-1-one | 82784-35-8

• 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: (2E,4E)-1-(4-aminophenyl)-5-phenylpenta-2,4-dien-1-one
• 英文别名: 5t-phenyl-1-(4-amino-phenyl)-pentadien-(2t.4)-one-(1)；5t-Phenyl-1-(4-amino-phenyl)-pentadien-(2t.4)-on-(1)
• CAS: 82784-35-8
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: CHSZEINKMPNOBR-KBXRYBNXSA-N

物化性质

• 熔点：
  159-160 °C
• 沸点：
  460.8±45.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-1-(4-aminophenyl)-5-phenylpenta-2,4-dien-1-one 、 氯乙酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-chloro-N-(4-((2E,4E)-5-phenylpenta-2, 4-dienoyl)phenyl)acetamide
  参考文献：
  名称：

  Discovery of novel AHLs as potent antiproliferative agents

  摘要：

  Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog lie induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.026
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 (2E,4E)-1-(4-aminophenyl)-5-phenylpenta-2,4-dien-1-one
  参考文献：
  名称：

  Marrian; Russell; Todd, Journal of the Chemical Society, 1947, p. 1419

  摘要：

  DOI：

文献信息

• Synthesis, structural characterization, and cytotoxic evaluation of chalcone derivatives
  作者：Paulo N. Bandeira、Telma L. G. Lemos、Hélcio S. Santos、Mylena C. S. de Carvalho、Daniel P. Pinheiro、Manoel O. de Moraes Filho、Cláudia Pessoa、Francisco W. A. Barros-Nepomuceno、Tigressa H. S. Rodrigues、Paulo R. V. Ribeiro、Herbert S. Magalhães、Alexandre M. R. Teixeira

  DOI：10.1007/s00044-019-02434-1

  日期：2019.11

  Chalcones containing amino or acetamide groups on ring A and electron donating/withdrawing groups on ring B have been shown to have great cytotoxic potential against human cancer cell lines. In this work, a series of twenty chalcones, including nine 1-(4′-aminophenyl)-3-(substituted aryl)-2-propen-1-ones (1–9), nine 1-(4′-acetamidophenyl)-3-(substituted aryl)-2-propen-1-ones (1a–9a), and two 1-(3′

  已显示，在A环上含有氨基或乙酰胺基，在B环上具有供电子/吸电子基团的查耳酮对人癌细胞具有巨大的细胞毒性潜能。在这项工作中，一系列20米的查耳酮，包括9 1-（4'-氨基苯基）-3-（取代的芳基）-2-丙烯-1-酮（1 - 9），九1-（4'-乙酰胺基苯基） -3-（取代的芳基）-2-丙烯-1-酮（1a – 9a）和两个1-（3'-甲氧基-4'-羟基苯基）-3-（取代的芳基）-2-丙烯-1-酮（10，11），合成并提交用于使用HCT-116细胞的初始生物筛选。在评估的化合物中，查尔酮6a对HCT-116细胞具有强而有选择性的活性（IC50  = 2.37±0.73 µM）。初步构效关系分析表明，这些化合物的细胞毒性作用可能是由于结合的两个吸电子基团的效果：硝基（NO 2在）元环B的位和在乙酰基对位孵育24小时后，查耳酮6a能够以10 µM的浓度诱导G2 / M细胞周期阻滞和凋亡。这些数据加强
• PORTNYAGINA, V. A.;KLYUSHIN, V. V., YKP. XIM. ZH., 1982, 48, N 4, 399-401
  作者：PORTNYAGINA, V. A.、KLYUSHIN, V. V.

  DOI：——

  日期：——
• Discovery of novel AHLs as potent antiproliferative agents
  作者：Jing-Li Ren、Xu-Yao Zhang、Bin Yu、Xi-Xin Wang、Kun-Peng Shao、Xiao-Ge Zhu、Hong-Min Liu

  DOI：10.1016/j.ejmech.2015.02.026

  日期：2015.3

  Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog lie induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Marrian; Russell; Todd, Journal of the Chemical Society, 1947, p. 1419
  作者：Marrian、Russell、Todd

  DOI：——

  日期：——