1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-2-propen-1-one | 77129-49-8

• 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: 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-2-propen-1-one
• 英文别名: 2’,6’-dihydroxy-4’-methoxychalcone；2′,6′-dihydroxy-4′-methoxychalcone；1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropenone；2',6'-dihydroxy-4'-methoxychalcone；pinostrobin chalcone；piperetol；2-Propen-1-one, 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-, (E)-; Chalcone, 2',6'-dihydroxy-4'-methoxy-; 2',6'-Dihydroxy-4'-methoxychalcone；1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one
• CAS: 77129-49-8
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: CUGDOWNTXKLQMD-UHFFFAOYSA-N

物化性质

• 沸点：
  521.1±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-2-propen-1-one 在 5%-palladium/activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.0h， 生成 (+)-hostmanin A
  参考文献：
  名称：

  Enantioselective Total Syntheses of (+)-Hostmanin A, (−)-Linderol A, (+)-Methyllinderatin and Structural Reassignment of Adunctin E

  摘要：

  A one-step protocol has been developed for the enantioselective synthesis of hexahydrodibenzofuran derivatives using a modified Friedel-Crafts reaction. The developed method was applied to the synthesis of a series of natural products including (+)-hostmanin A, (+)-methyllinderatin, and (-)-linderol A. The synthetic and spectroscopic data investigations led to the structural. reassignment of natural product adunctin E, which was further confirmed by single-crystal X-ray analysis.

  DOI：

  10.1021/acs.joc.5b00331
• 作为产物：
  描述：

  1-(2-hydroxy-4-methoxy-6-propan-2-yloxyphenyl)-3-phenylprop-2-en-1-one 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-2-propen-1-one
  参考文献：
  名称：

  Evaluation of the Anti-Inflammatory Effect of Chalcone and Chalcone Analogues in a Zebrafish Model

  摘要：

  本研究的目的是调查具有强效体内抗炎活性的新型查尔酮。研究人员利用尾鳍受伤的转基因斑马鱼品系 "Tg(mpx:gfp) "对查尔酮和两种查尔酮类似物（化合物 5 和 9）进行了评估，以动态观察中性粒细胞招募的影响。结果表明，用化合物 9 处理不仅会影响伤口诱导的中性粒细胞募集，还会影响 Mpx 酶的活性。此外，促炎因子（Mpx、NFκB 和 TNFα）的蛋白表达水平也受到化合物 9 的调控。综上所述，我们的研究结果为合成的查尔酮类似物对伤口引起的炎症具有抗炎作用提供了体内证据。

  DOI：

  10.3390/molecules18022052

文献信息

• 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。
• A novel one-pot synthesis of flavones
  作者：Meng-Yang Chang、Min-Chen Tsai、Chun-Yi Lin

  DOI：10.1039/d1ra00534k

  日期：——

  In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecular ortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resulting o-hydroxychalcones. The reaction conditions are discussed herein.

  在本文中，描述了一种由 BiCl 3 /RuCl 3介导的功能化黄酮合成的简便途径，包括：(i)用肉桂酰氯对取代酚进行分子间邻位酰化，以及 (ii)得到邻羟基查耳酮。本文讨论了反应条件。
• Electron Transfer-Initiated Diels−Alder Cycloadditions of 2′-Hydroxychalcones
  作者：Huan Cong、Dustin Ledbetter、Gerard T. Rowe、John P. Caradonna、John A. Porco

  DOI：10.1021/ja803094u

  日期：2008.7.1

  An efficient approach to cyclohexenyl chalcones employing highly electron rich 2'-hydroxychalcone dienophiles via electron transfer-initiated Diels-Alder cycloaddition is described. Using the methodology, the total synthesis of nicolaiodesin C has been accomplished.
• Enantioselective Total Syntheses of (+)-Hostmanin A, (−)-Linderol A, (+)-Methyllinderatin and Structural Reassignment of Adunctin E
  作者：Dattatraya H. Dethe、Balu D. Dherange

  DOI：10.1021/acs.joc.5b00331

  日期：2015.5.1

  A one-step protocol has been developed for the enantioselective synthesis of hexahydrodibenzofuran derivatives using a modified Friedel-Crafts reaction. The developed method was applied to the synthesis of a series of natural products including (+)-hostmanin A, (+)-methyllinderatin, and (-)-linderol A. The synthetic and spectroscopic data investigations led to the structural. reassignment of natural product adunctin E, which was further confirmed by single-crystal X-ray analysis.
• Evaluation of the Anti-Inflammatory Effect of Chalcone and Chalcone Analogues in a Zebrafish Model
  作者：Yau-Hung Chen、Wei-Hua Wang、Yun-Hsin Wang、Zi-Yu Lin、Chi-Chung Wen、Ching-Yuh Chern

  DOI：10.3390/molecules18022052

  日期：——

  The aim of this study was to investigate novel chalcones with potent anti-inflammatory activities in vivo. Chalcone and two chalcone analogues (compound 5 and 9) were evaluated using a caudal fin-wounded transgenic zebrafish line “Tg(mpx:gfp)” to visualize the effect of neutrophil recruitment dynamically. Results showed that treatment with compound 9 not only affected wound-induced neutrophil recruitment, but also affected Mpx enzymatic activity. Moreover, protein expression levels of pro-inflammatory factors (Mpx, NFκB, and TNFα) were also regulated by compound 9. Taken together, our results provide in vivo evidence of the anti-inflammatory effects of synthesized chalcone analogues on wound-induced inflammation.

  本研究的目的是调查具有强效体内抗炎活性的新型查尔酮。研究人员利用尾鳍受伤的转基因斑马鱼品系 "Tg(mpx:gfp) "对查尔酮和两种查尔酮类似物（化合物 5 和 9）进行了评估，以动态观察中性粒细胞招募的影响。结果表明，用化合物 9 处理不仅会影响伤口诱导的中性粒细胞募集，还会影响 Mpx 酶的活性。此外，促炎因子（Mpx、NFκB 和 TNFα）的蛋白表达水平也受到化合物 9 的调控。综上所述，我们的研究结果为合成的查尔酮类似物对伤口引起的炎症具有抗炎作用提供了体内证据。