2-丙烯-1-酮,1-(3-羟基苯基)-3-(4-羟基苯基)-,(2E)-

• 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
• 中文名称: 2-丙烯-1-酮,1-(3-羟基苯基)-3-(4-羟基苯基)-,(2E)-
• 英文名称: 3',4-dihydroxychalcone
• 英文别名: 1-(3-Hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one；1-(3-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: VXDWUWKYEMWDDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丙烯-1-酮,1-(3-羟基苯基)-3-(4-羟基苯基)-,(2E)- 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-(5-(4-hydroxyphenyl)-4,5-dihydroisoxazol-3-yl)phenol
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Some New Isoxazoline Derivatives

  摘要：

  异噁唑啉是一类独特的含氮和含氧的五元杂环化合物，这类化合物在生物化学中具有重要意义。异噁唑啉被认为是最有效的抗菌化合物之一。研究发现，异噁唑啉衍生物对结核分枝杆菌具有显著的抗结核活性。由于结核药物耐药性事件的增加，抗结核药物发现的目标变得更加具有挑战性。本研究旨在合成高效的抗结核异噁唑啉衍生物。通过在羟胺 hydrochloride 存在下对取代的查尔酮衍生物进行环化，合成了不同取代的异噁唑啉衍生物。合成的衍生物通过熔点、薄层色谱 (TLC)、傅里叶变换红外光谱 (FT-IR)、质子核磁共振 (1H NMR) 和质谱 (MS) 进行表征。合成的化合物在体外抗结核活性方面与异烟肼进行了比较，获得了相似的抗结核活性。

  DOI：

  10.14233/ajchem.2013.12899
• 作为产物：
  描述：

  β-dimethylamino-m-hydroxypropiophenone hydrochloride 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.67h， 生成 2-丙烯-1-酮,1-(3-羟基苯基)-3-(4-羟基苯基)-,(2E)-
  参考文献：
  名称：

  酚的分子内烷基化。第4部分。酚醛酮的碱催化环化。范围和局限性

  摘要：

  酚烯酮（4），（5），（8），（9）和（13）在酸性条件下容易环化。然而，这些以及稀取代的酚（11a），（13a），（14a）和（15a）在碱性条件下均未关闭。不利的均衡被卷入其中。与饱和酮（38）和醛（39）的相关成功环化进行了比较。初步结果表明，严格的立体电子学要求对于烯酮环闭合是必需的，并且在一般类型的酚的碱催化的5-内-和6-内-三角环闭合中不满足这些条件（2；n = 0并且n = 1）。

  DOI：

  10.1039/p19800001555

文献信息

• Reactions of aryl cyclopropyl ketones. A new synthesis of aryl tetralones
  作者：William S. Murphy、Sompong Wattanasin

  DOI：10.1039/p19810002920

  日期：——

  ketones (1) do not react. Stereoelectronic factors involved in the reactivity of the rigid cyclopropyl ketone (12) are discussed. The reactions of selected phenolic cyclopropyl ketones have been investigated as anionic counterparts to the acid-catalysed reactions. No reaction is observed.

  在各种酸催化剂的存在下，在温和的条件下，芳基环丙基酮（2）环化为1-四氢萘酮（3）。还形成开链甲醇（4）。（3）与（4）的比例取决于芳基环取代基。提出了阳离子机制。环丙基酮（1）不反应。讨论了涉及刚性环丙基酮（12）反应性的立体电子因素。已经研究了选择的酚环丙基酮的反应作为酸催化反应的阴离子对应物。没有观察到反应。
• Miquel,J.F., Bulletin de la Societe Chimique de France, 1961, p. 1369 - 1376
  作者：Miquel,J.F.

  DOI：——

  日期：——
• Dihydroxylated 2,4,6-triphenyl pyridines: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship study
  作者：Radha Karki、Pritam Thapa、Han Young Yoo、Tara Man Kadayat、Pil-Hoon Park、Youngwha Na、Eunyoung Lee、Kyung-Hwa Jeon、Won-Jea Cho、Heesung Choi、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2012.01.015

  日期：2012.3

  Twelve dihydroxylated 2,4,6-triphenyl pyridines were designed and synthesized which contain hydroxyl groups at ortho, meta or para position of 2- and 6-phenyl, or 2- and 4-phenyl rings attached to the central pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Generally, dihydroxylated 2,4,6-triphenyl pyridines exhibited stronger topoisomerase II inhibitory activity, and cytotoxicity compared to those of monohydroxylated 2,4,6-triphenyl pyridines. The concrete structure-activity relationship was observed that dihydroxylated 2,4,6-triphenyl pyridines with hydroxyl group at meta or para position of 2-phenyl ring displayed significant topoisomerase II inhibitory activity as well as cytotoxicity. Positive correlation between topoisomerase II inhibitory activity and cytotoxicity was observed for compounds 10, 12, 13, 17-20 and 22. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and pharmacological evaluation of some novel 2-pyrazolines bearing benzenesulfonamide as anti-inflammatory and blood glucose lowering agents
  作者：Syed Ovais、Rafia Bashir、Shafiya Yaseen、Pooja Rathore、Mohammed Samim、Kalim Javed

  DOI：10.1007/s00044-012-0130-y

  日期：2013.3

  A series of novel pyrazolines (2a-l) bearing benzenesulfonamide moiety were synthesized by condensing appropriate chalcone (1a-l) with 4-hydrazinobenzenesulfonamide hydrochloride. Structure of all novel synthesized compounds was characterized on basis of elemental analysis data and spectral data (IR, (HNMR)-H-1, MS). Compounds (2a-l) were screened for in vivo anti-inflammatory action in carrageenan-induced rat paw edema model and blood glucose lowering action in glucose fed hyperglycemic normal rats. Compounds 2a, 2e, and 2l showed significant anti-inflammatory action (more than 75 %) at 5 h and also showed superior gastrointestinal safety profiles as compared to celecoxib. One compound (2i) was found to exhibit significant blood glucose lowering activity.
• Discovery of dihydroxylated 2,4-diphenyl-6-thiophen-2-yl-pyridine as a non-intercalative DNA-binding topoisomerase II-specific catalytic inhibitor
  作者：Kyu-Yeon Jun、Hanbyeol Kwon、So-Eun Park、Eunyoung Lee、Radha Karki、Pritam Thapa、Jun-Ho Lee、Eung-Seok Lee、Youngjoo Kwon

  DOI：10.1016/j.ejmech.2014.04.066

  日期：2014.6

  We describe our rationale for designing specific catalytic inhibitors of topoisomerase II (topo II) over topoisomerase I (topo I). Based on 3D-QSAR studies of previously published dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives, 9 novel dihydroxylated 2,4-diphenyl-6-thiophen-2-yl pyridine compounds were designed, synthesized, and their biological activities were evaluated. These compounds have 2-thienyl ring substituted on the R(3) group on the pyridine ring and they all showed excellent specificity toward topo II compared to topo I. In vitro experiments were performed for compound 13 to determine the mechanism of action for this series of compounds. Compound 13 inhibited topoisomerase II specifically by non-intercalative binding to DNA and did not stabilize enzyme-cleavable DNA complex. Compound 13 efficiently inhibited cell viability, cell migration, and induced G1 arrest. Also from 3D-QSAR studies, the results were compared with other previously published dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives to explain the structure-activity relationships.