(2E)-1-(3'-nitrophenyl)-3-(1-naphthyl)-2-propen-1-one | 1098176-43-2

• 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: (2E)-1-(3'-nitrophenyl)-3-(1-naphthyl)-2-propen-1-one
• 英文别名: 3-(1-Naphthyl)-1-(3-nitrophenyl)prop-2-en-1-one；(E)-3-naphthalen-1-yl-1-(3-nitrophenyl)prop-2-en-1-one
• CAS: 1098176-43-2
• 化学式: C₁₉H₁₃NO₃
• 分子量: 303.317
• InChiKey: KLHXSPUCBJTTFL-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴丙酮 、 (2E)-1-(3'-nitrophenyl)-3-(1-naphthyl)-2-propen-1-one 在 sodium hydroxide 、 Merrifield resin-bound pyridine 作用下， 生成 5-Naphthalen-1-yl-3'-nitro-biphenyl-3-ol
  参考文献：
  名称：

  聚合物支持的取代酚的制备：固相同时环化-裂解反应的新例子

  摘要：

  使用“环化裂解”方法以高收率合成了一系列不同取代的苯酚。α，β-不饱和酮与聚合物键合的丙酮基之间的碱催化反应导致串联的迈克尔加成/环化反应，然后消除并重排成酚。由于所有中间体都在树脂上直至最后一步，最终的反应产物仅含有所需的酚，而起始酮则为次要杂质。这种有效的一锅芳香环形成代表了固相合成的新变体。

  DOI：

  10.1016/s0040-4039(98)01771-7
• 作为产物：
  描述：

  1-萘甲醛 、 间硝基苯乙酮 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2E)-1-(3'-nitrophenyl)-3-(1-naphthyl)-2-propen-1-one
  参考文献：
  名称：

  Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum

  摘要：

  Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkylesters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5 +/- 0.8 mu M, 9.5 +/- 0.2 mu M and 4.9 +/- 1.3 mu M, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.

  DOI：

  10.3109/14756366.2014.920839

文献信息

• Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
  作者：Louise Domeneghini Chiaradia、Alessandra Mascarello、Marcela Purificação、Javier Vernal、Marlon Norberto Sechini Cordeiro、María Emilia Zenteno、Andréa Villarino、Ricardo José Nunes、Rosendo Augusto Yunes、Hernán Terenzi

  DOI：10.1016/j.bmcl.2008.09.105

  日期：2008.12

  In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were obtained by aldolic condensation between aldehydes and acetophenones, under basic conditions. Five compounds presented moderate or good activity. The structure - activity analysis reveals that the predominant factor for the activity is the molecule planarity/hydrophobicity and the nature of the substituents. (C) 2008 Elsevier Ltd. All rights reserved.
• Antihyperglycemic activity of naphthylchalcones
  作者：Rosangela Guollo Damazio、Ana Paula Zanatta、Luisa Helena Cazarolli、Louise Domeneghini Chiaradia、Alessandra Mascarello、Ricardo José Nunes、Rosendo Augusto Yunes、Fátima Regina Mena Barreto Silva

  DOI：10.1016/j.ejmech.2009.12.017

  日期：2010.4

  The purpose of the present work was to investigate, following previous works, naphthylchalcones as antihyperglycemic agent in glucose loaded animal model, insulin secretion as well as the action of these compounds on glucose uptake in a target tissue of insulin. The naphthylchalcones were found to have an acute serum glucose-lowering effect in hyperglycemic normal rats. In addition, chalcones 2 and 4 stimulated significantly the insulin secretion induced by glucose. These results suggest that the presence of nitro group and their position in the phenyl rings are responsible for the antihyperglycemic activity of chalcones. Additionally, the effect of chalcones on serum glucose-lowering seems to be a consequence of insulin secretion and these chalcones represent potential compounds with strong antihyperglycemic properties. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthetic compounds from an <i>in house</i> library as inhibitors of falcipain-2 from <i>Plasmodium falciparum</i>
  作者：Jean Borges Bertoldo、Louise Domeneghini Chiaradia-Delatorre、Alessandra Mascarello、Paulo César Leal、Marlon Norberto Sechini Cordeiro、Ricardo José Nunes、Emir Salas Sarduy、Philip Jon Rosenthal、Hernán Terenzi

  DOI：10.3109/14756366.2014.920839

  日期：2015.3.4

  Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkylesters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5 +/- 0.8 mu M, 9.5 +/- 0.2 mu M and 4.9 +/- 1.3 mu M, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.
• Polymer-supported preparation of substituted phenols: A new example of simultaneous cyclization-cleavage reaction on solid phase
  作者：Alan R Katritzky、Sergei A Belyakov、Yunfeng Fang、John S Kiely

  DOI：10.1016/s0040-4039(98)01771-7

  日期：1998.10

  A series of variously substituted phenols was synthesized in high yields using the “cyclization-cleavage” approach. Base-catalyzed reactions between α,β-unsaturated ketones and polymer-bound acetonyl groups result in a tandem Michael addition/annulation reaction followed by elimination and rearrangement into phenols. Since all intermediates are on the resin until the last stage, the final reaction

  使用“环化裂解”方法以高收率合成了一系列不同取代的苯酚。α，β-不饱和酮与聚合物键合的丙酮基之间的碱催化反应导致串联的迈克尔加成/环化反应，然后消除并重排成酚。由于所有中间体都在树脂上直至最后一步，最终的反应产物仅含有所需的酚，而起始酮则为次要杂质。这种有效的一锅芳香环形成代表了固相合成的新变体。