(2E)-3-(2,5-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one | 145626-28-4

• 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)-3-(2,5-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 2,5-dimethoxy-2'-hydroxychalcone；2,5dimethoxy-2'-hydroxy-chalcone；(E)-3-(2,5-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 145626-28-4
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: URPAREMBXBSUFI-VQHVLOKHSA-N

物化性质

• 沸点：
  472.3±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-3-(2,5-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 3-(2,5-Dimethoxyphenyl)-1-(2-hydroxyphenyl)-1-propanone
  参考文献：
  名称：

  Trikha, Smriti; Kumar, Rajesh; Dhawan, Ashish, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 2, p. 356 - 365

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 sodium hydroxide 、 oxonium 作用下， 以 乙醇 为溶剂， 生成 (2E)-3-(2,5-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of 4,6-disubstituted 3-cyanopyridin-2(1H)-ones, a new class of calcium entry blockers

  摘要：

  The preparation of 3-cyano-4,6-diaryl-pyridin-2(1H)-ones 4a . h, calcium entry blockers related to diltiazem, is described starting from 1,3-diaryl-2-propen-1-ones 5. On preliminary pharmacological tests all compounds are active and some of them show calcium antagonistic activity superior or comparable to diltiazem. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00361-9

文献信息

• Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin
  作者：Tatiana A. Dias、Cecília L. Duarte、Cristovao F. Lima、M. Fernanda Proença、Cristina Pereira-Wilson

  DOI：10.1016/j.ejmech.2013.04.064

  日期：2013.7

  chalcones whereas for flavonol derivatives the best performance was registered for the 4-substituted derivatives. Flow cytometry analysis showed that compounds 3p and 4o induced cell cycle arrest and apoptosis as demonstrated by increased S, G2/M and sub-G1 phases. These data were corroborated by western blot and fluorescence microscopy analysis. In summary, halogenated chalcones and flavonols were successfully

  通过生态友好的方法以高收率合成了一系列查尔酮和黄酮醇衍生物。用人结肠直肠癌细胞系HCT116进行药理评估，结果表明黄酮醇的抗癌活性高于查尔酮前体的抗癌活性。卤代衍生物的抗增殖活性随着B环的3-位或4-位正位的取代基从F到Cl和Br的增加而增加。此外，位置3的卤素增强了查耳酮的抗癌活性，而对于黄酮醇衍生物而言，4-取代衍生物的最佳性能则得到了证明。流式细胞仪分析表明化合物3p和4oS，G2 / M和sub-G1期增加证明细胞周期阻滞和凋亡。这些数据通过蛋白质印迹和荧光显微镜分析得到证实。总之，成功制备了卤代查耳酮和黄酮醇，并表现出很高的抗癌活性，如它们的细胞生长和对HCT116细胞的细胞周期抑制潜能（优于槲皮素）所显示的那样，它们被用作阳性对照。
• Synthesis of a library of glycosylated flavonols
  作者：Zhitao Li、George Ngojeh、Paul DeWitt、Zhi Zheng、Min Chen、Brendan Lainhart、Vincent Li、Peter Felpo

  DOI：10.1016/j.tetlet.2008.10.032

  日期：2008.12

  products isolated from plants. Some glycosylated flavonols showed very interesting biological activities. A library of flavonols has been made through Algar-Flynn-Oyamada reaction from 2'-hydroxyacetophenones and benzaldehydes. Glycosylation of these flavonols with various glycosyl donors affords a library of glycosylated flavonols. These compounds are potentially useful pharmacologically active compounds

  黄酮醇是从植物中分离出来的一类重要的天然产物。一些糖基化的黄酮醇表现出非常有趣的生物学活性。通过Algar-Flynn-Oyamada反应，由2'-羟基苯乙酮和苯甲醛制得黄酮醇。这些黄酮醇与各种糖基供体的糖基化提供了糖基化黄酮醇的文库。这些化合物可能是有用的药理活性化合物，并将对其生物学活性进行研究。
• Synthesis of 1,5-Benzodiazepines with Unusual Substitution Pattern from Chalcones Under Solvent-Free Microwave Irradiation Conditions
  作者：Carlos A. Escobar、Oscar Donoso-Tauda、Ramiro Araya-Maturana、Dieter Sicker

  DOI：10.1080/00397910802372517

  日期：2008.12.16

  Abstract 1,5-Benzodiazepines have been synthesized from the corresponding 2′-hydroxychalcones [1-(2-hydroxyphenyl)-3-aryl-2-propen-1-ones] and o-phenylenediamine, both in methanol, under reflux and under solvent-free microwave irradiation conditions on alumina. The latter method proved to be advantageous.

  摘要 1,5-苯二氮卓类化合物由相应的 2'-羟基查尔酮 [1-(2-羟基苯基)-3-芳基-2-丙烯-1-酮] 和邻苯二胺在甲醇中、回流下和无溶剂微波辐照条件对氧化铝的影响。后一种方法被证明是有利的。
• Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones
  申请人：Statens Serum Institute

  公开号：US20030065039A1

  公开（公告）日：2003-04-03

  The invention relates to the use of 1,3-bis-aromatic-prop-2-en-1-ones (chalcones), 1,3-bis-aromatic-propan-1-ones (dihydrochalcones), and 1,3-bis-aromatic-prop-2-yn-1-ones for the preparation of pharmaceutical compositions for the treatment or prophylaxis of a number of serious diseases including i) conditions relating to harmful effects of inflammatory cytokines, ii) conditions involving infection by Helicobacter species, iii) conditions involving infection by viruses, iv) neoplastic disorders, and v) conditions caused by microorganisms or parasites. The invention also relates to novel chalcones and dihydrochalcones (especially alkoxy substituted variants) having advantageous substitution patterns with respect to their effect as drug substances, and to methods of preparing them, as well as to pharmaceutical compositions comprising the novel chalcones. Moreover, the present invention relates to a method for the isolation of Leishmania fumarate reductase, QSAR methodologies for selecting potent compounds for the above-mentioned purposes.

  该发明涉及使用1,3-双芳基-丙-2-烯-1-酮（香豆素）、1,3-双芳基-丙酮-1-酮（二氢香豆素）和1,3-双芳基-丙-2-炔-1-酮制备用于治疗或预防多种严重疾病的药物组合物，包括i）与炎症细胞因子有害作用相关的疾病，ii）涉及幽门螺旋杆菌感染的疾病，iii）涉及病毒感染的疾病，iv）肿瘤性疾病，v）由微生物或寄生虫引起的疾病。该发明还涉及新型香豆素和二氢香豆素（特别是烷氧基取代变体），其具有有利的取代模式，对其作为药物物质的效果，以及制备它们的方法，以及包含新型香豆素的药物组合物。此外，本发明涉及一种用于分离利什曼氏弓形虫富马酸还原酶的方法，以及用于选择上述目的的有效化合物的QSAR方法。
• Domino synthesis of novel 3-alkenyl benzofuran derivatives- base mediated condensation cascade reaction
  作者：Priyanka Mundhe、Neeru Bhanwala、Surbhi Mahender Saini、Gopavaram Sumanth、Kondreddy Shivaprasad、Sondarya Uttam Shende、Krishna Reddy、Sandeep Chandrashekharappa

  DOI：10.1016/j.tet.2023.133265

  日期：2023.2

  been developed via a green method. Products are obtained from 2-hydroxy chalcone with Phenacyl bromide, Bromo acetonitrile, and/or Ethyl-2-bromo acetate via an alkylation followed by a condensation reaction. This methodology features faster condensation over Michael addition, transition metal, catalyst-free medium, and an environmentally friendly synthetic route toward the synthesis of substituted 3-alkenyl

  通过绿色方法开发了一种药理学相关分子结构的一锅法高效构建方法，即 3-烯基苯并呋喃，收率高。产品由 2-羟基查耳酮与苯甲酰溴、溴乙腈和/或 2-溴乙酸乙酯通过烷基化反应然后缩合反应获得。该方法的特点是比迈克尔加成、过渡金属、无催化剂介质更快地缩合，以及一种环境友好的合成路线，用于合成取代的 3-烯基苯并呋喃。