(E)-1-(4-aminophenyl)-3-(3-nitrophenyl)prop-2-en-1-one | 952578-25-5

• 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)-1-(4-aminophenyl)-3-(3-nitrophenyl)prop-2-en-1-one
• 英文别名: 4'-Amino-3-nitrochalcone
• CAS: 952578-25-5
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: UPORNSJTCPUYNK-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-aminophenyl)-3-(3-nitrophenyl)prop-2-en-1-one 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 7-(4-((4-((E)-3-(3-nitrophenyl)acryloyl)phenylcarbamoyl)methyl)-piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase I and II inhibitory activity

  摘要：

  A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI(50) level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 gI A and 20 mu M concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 RM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 laM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a j compared to the parent ciprofloxacin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.040
• 作为产物：
  描述：

  间硝基苯甲醛 、 4-氨基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以68%的产率得到(E)-1-(4-aminophenyl)-3-(3-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  查耳酮作为H1N1神经氨酸酶抑制剂的设计，合成和评估

  摘要：

  基于异寡糖原蛋白（最活跃的天然查尔酮非竞争性神经氨酸酶（NA）抑制剂）设计了一系列查尔酮衍生物（1a – 2i）。分子模型研究表明，异寡糖原蛋白及其设计的类似物占据了NA的430环腔，并与催化位点残基相互作用。合成了有利的衍生物，并评价了其对H1N1病毒的细胞毒性和对细胞病变作用的抑制作用。通过血凝（HA）测定，H1N1-NA抑制和抑制动力学进一步量化了抑制作用。HA分析表明，化合物1e的最低EC 50为1.71 nM。相反，H1N1-NA抑制试验显示化合物1f具有3.58μM的IC 50最佳活性。酶动力学研究表明化合物1f和2f的抑制机理是非竞争性的。

  DOI：

  10.1007/s00044-017-2124-2

文献信息

• Design, synthesis and evaluation of chalcones as H1N1 Neuraminidase inhibitors
  作者：Anand S. Chintakrindi、Devanshi J. Gohil、Sweta T. Kothari、Abhay S. Chowdhary、Meena A. Kanyalkar

  DOI：10.1007/s00044-017-2124-2

  日期：2018.4

  A series of chalcone derivatives (1a–2i) were designed based on isoliquiritigenin (the most active natural chalcone non-competitive neuraminidase (NA) inhibitor). Molecular modeling studies revealed that isoliquiritigenin and its designed analogs occupied 430-loop cavity of NA and interacted favorably with catalytic site residues. The favorable derivatives were synthesized and evaluated for cytotoxicity

  基于异寡糖原蛋白（最活跃的天然查尔酮非竞争性神经氨酸酶（NA）抑制剂）设计了一系列查尔酮衍生物（1a – 2i）。分子模型研究表明，异寡糖原蛋白及其设计的类似物占据了NA的430环腔，并与催化位点残基相互作用。合成了有利的衍生物，并评价了其对H1N1病毒的细胞毒性和对细胞病变作用的抑制作用。通过血凝（HA）测定，H1N1-NA抑制和抑制动力学进一步量化了抑制作用。HA分析表明，化合物1e的最低EC 50为1.71 nM。相反，H1N1-NA抑制试验显示化合物1f具有3.58μM的IC 50最佳活性。酶动力学研究表明化合物1f和2f的抑制机理是非竞争性的。
• Inhibitory potential of some chalcones on cathepsins B, H and L
  作者：Shweta Garg、Neera Raghav

  DOI：10.1039/c5ra12856k

  日期：——

  Cathepsins, intracellular proteases, are known to be involved in a number of physiological processes such as degradation of extracellular proteins, prohormone processing, progressions of atherosclerosis etc.

  卡特普辛是细胞内蛋白酶，已知参与多种生理过程，如降解细胞外蛋白、前激素加工、动脉粥样硬化进展等。
• 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
• Structure based medicinal chemistry-driven strategy to design substituted dihydropyrimidines as potential antileishmanial agents
  作者：Umer Rashid、Riffat Sultana、Nargis Shaheen、Syed Fahad Hassan、Farhana Yaqoob、Muhammad Jawad Ahmad、Fatima Iftikhar、Nighat Sultana、Saba Asghar、Masoom Yasinzai、Farzana Latif Ansari、Naveeda Akhter Qureshi

  DOI：10.1016/j.ejmech.2016.03.022

  日期：2016.6

  In an attempt to explore novel and more potent antileishmanial compounds to diversify the current inhibitors, we pursued a medicinal chemistry-driven strategy to synthesize novel scaffolds with common pharmacophoric features of dihydropyrimidine and chalcone as current investigational antileishmanial compounds. Based on the reported X-ray structure of Pteridine reductase 1 (PTR1) from Leishmania major

  为了探索新型和更有效的抗风白蚁化合物以使目前的抑制剂多样化，我们采用了药物化学驱动的策略来合成具有二氢嘧啶和查耳酮的共同药理学特征的新型支架，作为目前研究的抗风白蚁化合物。基于报道的来自利什曼原虫（Leishmania major）的蝶啶还原酶1（PTR1）的X射线结构，我们设计了许多基于二氢嘧啶的衍生物，以在PTR1活性位点进行特异性相互作用。我们的先导化合物8i对L. Major和Leishmania donovani的前鞭毛体显示出有效的体外抗疟药活性，IC50值分别为0.47杯/毫升和1.5杯/毫升。出色的体外活性最终表明，我们的先导化合物足以根除内脏和局部利什曼病。此外，还进行了对接分析和计算机模拟ADMET。预测的分子特性支持了我们的实验分析，即这些化合物具有消除内脏和局部利什曼病的潜力。
• Anxiolytic-like effect of chalcone N-{4’[(2E)-3-(3-nitrophenyl)-1-(phenyl)prop-2-en-1-one]} acetamide on adult zebrafish (Danio rerio): Involvement of the 5-HT system
  作者：Maria Kueirislene Amâncio Ferreira、Antonio Wlisses da Silva、Francisca Crislândia Oliveira Silva、Antônio Eufrásio Vieira Neto、Adriana Rolim Campos、Sacha Aubrey Alves Rodrigues Santos、Alexandre Magno Rodrigues Teixeira、Jayze da Cunha Xavier、Paulo Nogueira Bandeira、Carlos Emídio Sampaio Nogueira、Débora Hellen Almeida de Brito、Emanuela Lima Rebouças、Francisco Ernani Alves Magalhães、Jane Eire Silva Alencar de Menezes、Hélcio Silva dos Santos

  DOI：10.1016/j.bbrc.2020.03.129

  日期：2020.5

  The action of anxiolytic compounds that act on selective serotonin receptors (SSRIs) have been scarcely evaluated. Serotonergic drugs have been shown to be effective in treating anxiety without presenting adverse effects as benzodiazepines. However, the anxiolytic effects take days to occur. This study aimed to evaluate the anxiolytic effect of the synthetic chalcone, 4'-[(2E)-3-(3-nitrophenyl)-1-(phenyl) prop-2-en-1-one] acetamide (PAAMNBA), and its possible mechanism of action in adult zebrafish (Danio rerio). PAAMNBA was synthesized with a yield of 51.3% and its chemical structure was determined by H-1 and C-13 NMR. Initially, PAAPMNBA was intraperitoneally administered to zebrafish (n = 6/group) at doses of 4,12, or 40 mg/kg, and the animals were subsequently subjected to acute and open field toxicity tests. PAAMNBA was administered to the other groups (n = 6/group) for analyzing its effect in the light and dark test. The involvement of the serotonergic (5HT) system was also evaluated using 5-HTR 1, 5-HTR 2A/2C, and 5-HTR 3A/36 receptor antagonists, namely, pizotifeo, granizetron, and ciproeptadina, respectively. Molecular coupling was performed using the 5-HT1 receptor. PAAMNBA was found to be nontoxic, reduced the locomotor activity, and had an anxiolytic effect in adult zebrafish. The effect was reduced by pretreatment with pizotifene and was not reversed by treatment with granizetron and cyproeptadine. A previous in vivo molecular coupling study indicated that chalcones interact with the 5-HT1 receptor. The results suggested that the chalcone, PAAPMNBA, has anxiolytic activity, that is mediated by the serotonergic system via the 5-HT1 receptor. The interaction of PAAPMNBA with the 5-HT1 receptor was confirmed by molecular docking studies. (C) 2020 Elsevier Inc. All rights reserved.