N-(4′-[(2E)-3-(4-chlorophenyl)-1-(phenyl)prop-2-en-1-one])acetamide

• 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: N-(4′-[(2E)-3-(4-chlorophenyl)-1-(phenyl)prop-2-en-1-one])acetamide
• 英文别名: (2E)-1-(4-acetylaminophenyl)-3-(4-chlorophenyl)prop-2-enone；N-{4-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]phenyl}acetamide；N-[4-[(E)-3-(4-chlorophenyl)prop-2-enoyl]phenyl]acetamide
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: WECPPTHNJWHQCM-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4′-[(2E)-3-(4-chlorophenyl)-1-(phenyl)prop-2-en-1-one])acetamide 在 sodium acetate 、 一水合肼 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以89%的产率得到3-(4-acetylaminophenyl)-5-(4-chlorophenyl)-1H-pyrazoline
  参考文献：
  名称：

  Facile sonochemical synthesis of novel pyrazolyne derivates at ambient conditions

  摘要：

  Claisen-Schmidt condensation reaction of 4-acetamidoacetophenone with aromatic aldehydes under ultrasonic irradiation affords acetylaminochalcones (yields: 71-90%) which also under ultrasonic irradiation and in the presence of sodium acetate and acetic acid aqueous undergo facile and clean cyclocondensation with hydrazine to afford 3-(4-acetamidophenyl)-5-(aryl)-1-H-pyrazolines. The pyrazolines were obtained in good to excellent yields (81-89%), and were characterized by conventional spectral data. The work-up is simple and the results obtained indicate that, unlike classical heating, ultrasonic irradiation results in higher yields, shorter reaction times (1.5-2.3 h) and milder conditions. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.11.018
• 作为产物：
  描述：

  4-氨基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 N-(4′-[(2E)-3-(4-chlorophenyl)-1-(phenyl)prop-2-en-1-one])acetamide
  参考文献：
  名称：

  4'-Acetamidochalcone Derivatives as Potential Antinociceptive Agents

  摘要：

  合成了九种乙酰氨基查尔酮，并使用小鼠扭体试验评估其作为抗伤害药的效果。腹腔内给予所有化合物都比用于比较的两种参考镇痛药物（乙酰水杨酸和对乙酰氨基酚）更有效。 N-{4-[(2E)-3-(4-硝基苯基)丙-2-烯酰基]苯基}乙酰胺(6)是最有效的化合物，因此被选择进行更详细的研究。它在扭体试验中产生了剂量相关的抑制作用，其效力比标准药物强约 32 至 34 倍。在第二阶段的福尔马林试验和辣椒素试验中也有效。这些乙酰氨基查尔酮，特别是化合物6，可能进一步用作模型来获得新的、更有效的镇痛药物。

  DOI：

  10.3390/12040896

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
• Antimicrobial and Cytotoxicity Potential of Acetamido, Amino and Nitrochalcones
  作者：T. Tristão、F. Campos-Buzzi、R. Corrêa、R.C Cruz、V. Cechinel Filho、A. Bella Cruz

  DOI：10.1055/s-0032-1327610

  日期：——

  Background: Chalcones constitute one of the major classes of natural products belonging to the flavonoid family, and they have been reported as having a range of important therapeutic activities, including some chalcones are effective as antimicrobial agents. Currently, the search for new structures with antimicrobial activity has been intensified due to the emergence of many strains resistant to antibiotics currently used to treat infectious diseases.Method: 3 chalcone series (amino, acetamido and nitrochalcones) were prepared (23 compounds) and evaluated for their antimicrobial and cytotoxic potential. The effects of substituents on their respective activities also was evaluated.Results & Conclusion: The results showed that 4 aminochalcones (2, 4, 8, 9), 3 acetoamidochalcones (10, 14, 18) and 3 nitrochalcones (20, 22, 23), exhibited antifungal effects. The aminochalcones were more toxic than the acetamidochalcones, while the nitrochalcones did not present any toxic effect. It was verified that there seems to be structure-activity correlation in some electron-donating and withdrawing substituents groups in rings A and B of the synthetized chalcone analogues and its antifungal and cytotoxic activity.
• <i>N</i>-(4-((E)-3-Arylacryloyl)phenyl)acetamide Derivatives and their Antileishmanial Activity
  作者：Dency J. Pacheco、Jorge Trilleras、Jairo Quiroga、Jennifer Gutiérrez、Luis Prent、Tobinson Coavas、Juan C. Marín、Gabriela Delgado

  DOI：10.5935/0103-5053.20130203

  日期：——

  The antileishmanial activity of a series of enonic derivatives (chalcones) synthesized via Claisen-Schmidt condensation reactions assisted by ultrasonic radiation was characterized by analyzing their cytotoxicity against Leishmania (Viannia) panamensis promastigotes, a species responsible for over 90% of Leishmania cases in Colombia. Two compounds were active against Leishmania with selectivity indexes of LC50 EC50-1 (lethal concentration 50 and effective concentration 50) higher than 27 and 3, respectively. These results suggest that a substitution on one of the two chalcone rings (aromatic ring A) with oxygen is convenient. Compound 3g should be further investigated for its antileishmanial activity, especially for being easy to obtain in high yields, making it possible to produce drugs for the treatment of cutaneous leishmaniasis.