2,3'-dihydroxychalcone | 38270-24-5

• 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: 2,3'-dihydroxychalcone
• 英文别名: 3-(2-hydroxyphenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one；3-(2-hydroxyphenyl)-1-(3-hydroxyphenyl)propenone；2',3-Dihydroxy-chalkon；3-(2-hydroxyphenyl)-1-(3-hydroxyphenyl)-2-propen-1-one
• CAS: 38270-24-5
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: KAMRNYCNWDARJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：

  2,3'-dihydroxychalcone 、 1-[2-oxo-2-(thiophen-2-yl)ethyl]pyridinium iodide 在 ammonium acetate 、 溶剂黄146 作用下， 以48.6%的产率得到2-[2-(3-hydroxyphenyl)-6-(thiophen-2-yl)pyridin-4-yl]phenol
  参考文献：
  名称：

  Discovery of dihydroxylated 2,4-diphenyl-6-thiophen-2-yl-pyridine as a non-intercalative DNA-binding topoisomerase II-specific catalytic inhibitor

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.04.066
• 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 48.67h， 生成 2,3'-dihydroxychalcone
  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

• A simple and catalyst free one pot access to the pyrazolone fused 2,8-dioxabicyclo[3.3.1]nonanes
  作者：Chiranjeevi Bingi、Narender Reddy Emmadi、Madhu Chennapuram、Jagadeesh Babu Nanubolu、Krishnaiah Atmakur

  DOI：10.1039/c4ra07278b

  日期：——

  Synthesis of a series of novel aryl and heteroaryl fused 2,8-dioxabicyclo[3.3.1]nonanes (3) was accomplished by one pot, catalyst free reaction of 2-hydroxy chalcone (1) with 3-trifluoromethyl substituted pyrazolone (2) in xylene at reflux temperature. The role of the trifluoromethyl functional group in formation of 3 was confirmed by comparative studies with 3-methyl substituted pyrazolones (2c,d)

  通过一锅，2-羟基查耳酮（1）与3-三氟甲基取代的吡唑酮（2）的无催化剂反应，完成了一系列新颖的芳基和杂芳基稠合的2,8-二氧杂双环[3.3.1]壬烷（3）的合成。在回流温度下在二甲苯中。通过与3-甲基取代的吡唑啉酮（2c，d）的比较研究证实了三氟甲基官能团在3的形成中的作用，并给出了结果。
• 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。
• Pro-Angiogenic Effects of Chalcone Derivatives in Zebrafish Embryos in Vivo
  作者：Yau-Hung Chen、Chao-Yuan Chang、Chiung-Fang Chang、Po-Chih Chen、Ya-Ting Lee、Ching-Yuh Chern、Jen-Ning Tsai

  DOI：10.3390/molecules200712512

  日期：——

  The aim of this study was to investigate novel chalcones with potent angiogenic activities in vivo. Chalcone-based derivatives were evaluated using a transgenic zebrafish line with fluorescent vessels to real-time monitor the effect on angiogenesis. Results showed that the chalcone analogues did not possess anti-angiogenic effect on zebrafish vasculatures; instead, some of them displayed potent pro-angiogenic effects on the formation of the sub-intestinal vein. Similar pro-angiogenic effects can also be seen on wild type zebrafish embryos. Moreover, the expression of vegfa, the major regulator for angiogenesis, was also upregulated in their treatment. Taken together, we have synthesized and identified a series of novel chalcone-based derivatives as potent in vivo pro-angiogenic compounds. These novel compounds hold potential for therapeutic angiogenesis.

  本研究的目的是研究具有强效体内血管生成活性的新型查耳酮。研究人员利用带有荧光血管的转基因斑马鱼品系对查尔酮类衍生物进行了评估，以实时监测其对血管生成的影响。结果表明，查尔酮类似物对斑马鱼血管并不具有抗血管生成的作用，相反，其中一些类似物对肠下静脉的形成具有强效的促血管生成作用。野生型斑马鱼胚胎也有类似的促血管生成作用。此外，血管生成的主要调节因子 vegfa 的表达也在它们的处理过程中上调。综上所述，我们合成并鉴定了一系列新型查耳酮基衍生物，它们是强效的体内促血管生成化合物。这些新型化合物具有治疗血管生成的潜力。
• 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.