3-(2-methoxyphenyl)-1-(4-nitrophenyl)-propenone

• 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: 3-(2-methoxyphenyl)-1-(4-nitrophenyl)-propenone
• 英文别名: (E)-3-(2-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one；(E)-4'-nitro-2-methoxychalcone；(2E)-3-(2-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: GPTZGDOZQOHFFJ-DHZHZOJOSA-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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methoxyphenyl)-1-(4-nitrophenyl)-propenone 在 盐酸 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 (E)-1-(4-aminophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  杂化α-溴丙烯酰胺查耳酮。设计、合成和生物学评价

  摘要：

  查尔酮抗肿瘤特性的研究在过去几年中受到了极大的关注 两个新的大型系列 α-溴丙烯酰氨基查尔酮1a - m和2a - k在其结构中包含一对迈克尔受体，对应于 α-溴丙烯酰合成部分和查尔酮框架的 α,β-不饱和酮系统，并评估其对五种癌细胞系的抗增殖活性。与相应的氨基查耳酮相比，这种杂化衍生物表现出显着增加的抗肿瘤活性。最有前途的先导分子是1k , 1m和2j 。，对五种细胞系的活性最高。K562 细胞的流式细胞术显示，活性最强的化合物导致大部分细胞进入凋亡亚 G0-G1 峰。此外，化合物1k通过线粒体途径诱导细胞凋亡并激活 caspase-3。

  DOI：

  10.1016/j.bmcl.2009.02.038
• 作为产物：
  描述：

  邻甲氧基苯甲醛 、 对硝基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以72.59%的产率得到3-(2-methoxyphenyl)-1-(4-nitrophenyl)-propenone
  参考文献：
  名称：

  新型查尔酮骨架材料的合成及其生物活性

  摘要：

  Chalcones是含有两个芳香环的开链类黄酮，由3个碳原子的α-，β-不饱和羰基链连接。的，β对查尔酮的抗微生物活性负责的不饱和酮基在进一步化学修饰成各种杂环化合物中还具有广泛的用途。合成了一系列新的查尔酮衍生物，并通过光谱分析（IR，1H-NMR，13C-NMR，MS和元素分析）进行了表征，并使用以下方法评估了其对细菌（革兰氏阴性和革兰氏阳性）和真菌菌株的体外抗菌活性管稀释法。抗菌筛查结果显示，一些化合物系列1（MICpa = 1.16 µM），3（MICbs = 1.82 µM），6（MICan = 2.09 µM），8（MICec和se = 0.94和1.88 µM）和17（MICsa （ca = 0.91和1.81 µM）对革兰氏阳性和革兰氏阴性细菌和真菌菌株均显示出最有希望的抗菌活性，

  DOI：

  10.1007/s11164-020-04359-6

文献信息

• Chiral Phosphoric Acid Catalyzed Asymmetric Friedel–Crafts Alkylation of Indoles with Simple α,β-Unsaturated Aromatic Ketones
  作者：Hong-Ying Tang、Ai-Dang Lu、Zheng-Hong Zhou、Guo-Feng Zhao、Lian-Nian He、Chu-Chi Tang

  DOI：10.1002/ejoc.200700980

  日期：2008.3

  Asymmetric Michael-type Friedel–Crafts (F-C) alkylations of indoles with nonchelating α,β-unsaturated aromatic ketones catalyzed by a chiral H8-BINOL-based phosphoric acid were investigated. The reactions took place smoothly in the presence of only 2 mol-% of catalyst at room temperature to afford the desired F-C alkylation products in good yields and with moderate enantioselectivities.(© Wiley-VCH

  研究了由基于手性 H8-BINOL 的磷酸催化的吲哚与非螯合 α,β-不饱和芳族酮的不对称迈克尔型 Friedel-Crafts (FC) 烷基化反应。反应在室温下仅 2 mol% 的催化剂存在下顺利进行，以良好的收率和适度的对映选择性提供所需的 FC 烷基化产物。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany , 2008)
• Discovery of Highly Functionalized 5-hydroxy-2H-pyrrol-2-ones That Exhibit Antiestrogenic Effects in Breast and Endometrial Cancer Cells and Potentiate the Antitumoral Effect of Tamoxifen
  作者：Miguel Guerra-Rodríguez、Priscila López-Rojas、Ángel Amesty、Haidée Aranda-Tavío、Yeray Brito-Casillas、Ana Estévez-Braun、Leandro Fernández-Pérez、Borja Guerra、Carlota Recio

  DOI：10.3390/cancers14215174

  日期：——

  Tamoxifen improves the overall survival rate in hormone receptor-positive breast cancer patients. However, despite the fact that it exerts antagonistic effects on the ERα, it can act as a partial agonist, resulting in tumor growth in estrogen-sensitive tissues. In this study, highly functionalized 5-hydroxy-2H-pyrrol-2-ones were synthesized and evaluated by using ERα- and phenotype-based screening assays. Compounds 32 and 35 inhibited 17β-estradiol (E2)-stimulated ERα-mediated transcription of the luciferase reporter gene in breast cancer cells without inhibition of the transcriptional activity mediated by androgen or glucocorticoid receptors. Compound 32 regulated E2-stimulated ERα-mediated transcription by partial antagonism, whereas compound 35 caused rapid and non-competitive inhibition. Monitoring of 2D and 3D cell growth confirmed potent antitumoral effects of both compounds on ER-positive breast cancer cells. Furthermore, compounds 32 and 35 caused apoptosis and blocked the cell cycle of ER-positive breast cancer cells in the sub-G1 and G0/G1 phases. Interestingly, compound 35 suppressed the functional activity of ERα in the uterus, as demonstrated by the inhibition of E2-stimulated transcription of estrogen and progesterone receptors and alkaline phosphatase enzymatic activity. Compound 35 showed a relatively low binding affinity with ERα. However, its antiestrogenic effect was associated with an increased polyubiquitination and a reduced protein expression of ERα. Clinically relevant, a possible combinatory therapy with compound 35 may enhance the antitumoral efficacy of 4-hydroxy-tamoxifen in ER-positive breast cancer cells. In silico ADME predictions indicated that these compounds exhibit good drug-likeness, which, together with their potential antitumoral effects and their lack of estrogenic activity, offers a pharmacological opportunity to deepen the study of ER-positive breast cancer treatment.

  他莫昔芬可提高激素受体阳性乳腺癌患者的总生存率。然而，尽管他莫昔芬对ERα具有拮抗作用，但它也可以作为部分激动剂，导致雌激素敏感组织中的肿瘤生长。本研究合成了高度官能化的 5-羟基-2H-吡咯-2-酮，并通过基于 ERα 和表型的筛选试验对其进行了评估。化合物 32 和 35 可抑制乳腺癌细胞中 17β-estradiol (E2) 刺激的 ERα 介导的荧光素酶报告基因转录，而不会抑制雄激素或糖皮质激素受体介导的转录活性。化合物 32 通过部分拮抗作用调节 E2 刺激的 ERα 介导的转录，而化合物 35 则造成快速和非竞争性抑制。对二维和三维细胞生长的监测证实了这两种化合物对 ER 阳性乳腺癌细胞的强效抗肿瘤作用。此外，化合物 32 和 35 还能导致ER 阳性乳腺癌细胞凋亡，并阻止细胞周期进入亚 G1 期和 G0/G1 期。有趣的是，化合物 35 抑制了ERα在子宫中的功能活性，这表现在抑制了E2刺激的雌激素和孕激素受体转录以及碱性磷酸酶的酶活性。化合物 35 与 ERα 的结合亲和力相对较低。然而，其抗雌激素作用与多泛素化的增加和ERα蛋白表达的减少有关。在临床上，与化合物 35 进行联合治疗可能会增强 4-hydroxy-tamoxifen 对 ER 阳性乳腺癌细胞的抗肿瘤功效。硅学 ADME 预测表明，这些化合物具有良好的药物相似性，再加上它们潜在的抗肿瘤作用和缺乏雌激素活性，为深化 ER 阳性乳腺癌治疗研究提供了药理学机会。
• The ortho effect: copper-catalyzed highly enantioselective 1,4-conjugate addition of diethylzinc to chalcones
  作者：Lan-Tao Liu、Min-Can Wang、Wen-Xian Zhao、Yan-Li Zhou、Xiao-Dan Wang

  DOI：10.1016/j.tetasy.2005.11.031

  日期：2006.1

  The copper-catalyzed enantioselective 1,4-conjugate addition of diethylzinc to chalcones was investigated in the presence of a catalytic amount of NP-ferrocenyl ligands with central and planar chirality under mild conditions (0 degrees C -> rt). It was found that chalcones with ortho-substituents (from ortho-substituted benzaldehydes and acetophenone/substituted acetophenones) led to a dramatic improvement in the enantio selectivities. The (R)- and (S)-antipodes of the addition reaction were obtained with up to 92% ee after this transformation. (c) 2006 Published by Elsevier Ltd.
• Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives
  作者：P.M. Sivakumar、S. Prabu Seenivasan、Vanaja Kumar、Mukesh Doble

  DOI：10.1016/j.bmcl.2006.12.112

  日期：2007.3

  In order to develop relatively small molecules as antimycobacterial agents, twenty-five chalcones were synthesized, their activity was evaluated, and quantitative structure-activity relationship (QSAR) was developed. The synthesis was based on the Claisen-Schimdt scheme and the resultant compounds were tested for antitubercular activity by luciferase reporter phage (LRP) assay. Compound C-24 was found to be the most active (similar to 99%) in this series based on the percentage reduction in Relative Light Units at both 50 and 100 mu g/ml levels, followed by compound C-21. Four compounds at the 50 mu g/ml and eight compounds at the 100 mu g/ml showed activity above 90% level. QSAR model was developed between activity and spatial, topological, and ADME descriptors for the 50 mu g/ml data. The statistical measures such as r, r(2), q(2), and F values obtained for the training set were in acceptable range and hence this relationship was used for the test set. The predictive ability of the model is satisfactory (q(2) = 0.56) and it can be used for designing similar group of compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• Amberlyst-15 and Amberlite-200C: Efficient catalysts for aldol and cross-aldol condensation under ultrasound irradiation
  作者：Achraf Lahyani、Manef Chtourou、Mohamed Hédi Frikha、Mahmoud Trabelsi

  DOI：10.1016/j.ultsonch.2013.01.017

  日期：2013.9

  This paper presents an improved synthesis of trans-chalcones and alpha,alpha '-bis(arylmethylidene) cycloalkanones under ultrasound irradiation in the presence of commercial acid-resins as catalysts in solvent free conditions. Several trans-chalcones and alpha,alpha '-bis(arylmethylidene) cycloalkanones were synthesized in good yields and excellent selectivity in a short reaction time. (C) 2013 Elsevier B.V. All rights reserved.