2',4-Dihydroxy-3',4'-dimethoxychalcone | 193411-10-8

• 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: 2',4-Dihydroxy-3',4'-dimethoxychalcone
• 英文别名: 4,2'-dihydroxy-3',4'-dimethoxychalcone；heliannone A；4.2'-dihydroxy-3'.4'-dimethoxy-trans-chalcone；4.2'-Dihydroxy-3'.4'-dimethoxy-trans-chalkon；(E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 193411-10-8
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: RURQJVCNVGERHF-WEVVVXLNSA-N

物化性质

• 沸点：
  518.1±50.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  144-146°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 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：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2',4-Dihydroxy-3',4'-dimethoxychalcone 在 potassium fluoride 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以64%的产率得到(R,S)-4'-Hydroxy-7,8-dimethoxyflavanone
  参考文献：
  名称：

  向日葵品种的两种生物活性类黄酮-向日葵酮A和（R，S）-向日葵酮B的全合成。

  摘要：

  描述了最初从向日葵品种中分离出的两种生物活性类黄酮-向日葵酮A（1）和（R，S）-向日葵酮B（2）的总合成。

  DOI：

  10.1021/np000489+
• 作为产物：
  描述：

  1,2-dimethoxy-3-(methoxymethoxy)benzene 在 盐酸 、 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 18.25h， 生成 2',4-Dihydroxy-3',4'-dimethoxychalcone
  参考文献：
  名称：

  披针金鸡菊花瓣中黄酮类化合物及其相关化合物的便捷合成和生理活性。

  摘要：

  以Horner⁻Wadsworth⁻Emmons反应为关键反应，从O-甲基连苯三酚中成功合成了查尔酮、黄烷酮和黄酮醇，包括从金鸡菊花瓣中分离出的8-甲氧基布丁，总收率达到2⁻59%。以羟醛缩合反应为关键反应，还成功合成了包括leptosidin在内的Aurones，总产率为5-36%。B 环中带有 3,4-二羟基的查耳酮、黄烷酮、黄酮醇和橙酮均表现出较高的抗氧化活性。此外，B环上带有2,4-二羟基的查耳酮、黄烷酮、黄酮醇和橙酮均表现出优异的美白能力。

  DOI：

  10.3390/molecules23071671

文献信息

• Total Synthesis of Heliannone A and (<i>R</i>,<i>S</i>)-Heliannone B, Two Bioactive Flavonoids from <i>Helianthus </i><i>a</i><i>nnuus</i> Cultivars
  作者：Y. Koteswara Rao、C. Venkata Rao、P. Hari Kishore、D. Gunasekar

  DOI：10.1021/np000489+

  日期：2001.3.1

  The total synthesis of heliannone A (1) and (R,S)-heliannone B (2), two bioactive flavonoids originally isolated from Helianthus annuus cultivars, is described.

  描述了最初从向日葵品种中分离出的两种生物活性类黄酮-向日葵酮A（1）和（R，S）-向日葵酮B（2）的总合成。
• Differential effects of synthesized 2′-oxygenated chalcone derivatives: modulation of human cell cycle phase distribution
  作者：Yerra Koteswara Rao、Shih-Hua Fang、Yew-Min Tzeng

  DOI：10.1016/j.bmc.2004.03.014

  日期：2004.5

  Ten structurally related T-oxygenated chalcone derivatives, bearing either hydroxy and/or methoxy substituents oil the A and B rings, were synthesized through Claisen-Schmidt condensation. The synthesis procedure was relatively easy and had an acceptable yield. The in vitro cytotoxicities of these compounds against the human tumor cells such as Jurkat, U937 cells, and normal cells PHA stimulated PBMCs were investigated. Among those, compounds 1 (IC50 = 2.5 muM), 2 (1.7 muM), and 8 (3.2 muM) showed potent inhibitory activity toward Jurkat cell line. In parallel, compounds 1 (6.7 muM), 2 (1.5 muM), and 10 (5.3 muM) showed the highest activity against U937 cell line. However, the chalcones also inhibit the PHA stimulated PBMCs cells, but the IC50 values were relatively high when compared to the tumor cell line values. Studies were also on the effect of synthesized chalcones on the cell cycle phase distribution. In Jurkat cell line, compounds 7 and 9 showed the highest activity and the most striking effect in reduction of the percentage of cells in the S phase, which was associated with an increase of cells in G2/M phase. In U937 cell line, compound 3 increased the proportion of cells in the G0/G1 phase and reduced the proportion in S phase. In contrast, compounds 1, 9, and 10 showed a decrease effect on the percentage of cells in S phase and an increase effect on the percentage of cells in the G2/M phase of the cell cycle. Whereas in the case of PHA stimulated PBMCs, compounds 1, 4, 8, and 10 increased the percentage of cells in G2/M phase, which was associated with a decrease effect in the :S phase of the cell cycle. (C) 2004 Elsevier Ltd. All rights reserved.
• 58. The constitution of tannins. Part I. Reduction products of chalkones and the synthesis of a typical phlobatannin
  作者：Alfred Russell

  DOI：10.1039/jr9340000218

  日期：——
• Convenient Synthesis and Physiological Activities of Flavonoids in Coreopsis lanceolata L. Petals and Their Related Compounds
  作者：Daisuke Nakabo、Yuka Okano、Naomi Kandori、Taisei Satahira、Naoya Kataoka、Junpei Akamatsu、Yoshiharu Okada

  DOI：10.3390/molecules23071671

  日期：——

  with 5⁻36% total yields using the Aldol condensation reaction as a key reaction. Each chalcone, flavanone, flavonol, and aurone with the 3,4-dihydroxy groups in the B-ring showed high antioxidant activity. Additionally, each of the chalcones, flavanones, flavonols, and aurones with the 2,4-dihydroxy groups in the B-ring showed an excellent whitening ability.

  以Horner⁻Wadsworth⁻Emmons反应为关键反应，从O-甲基连苯三酚中成功合成了查尔酮、黄烷酮和黄酮醇，包括从金鸡菊花瓣中分离出的8-甲氧基布丁，总收率达到2⁻59%。以羟醛缩合反应为关键反应，还成功合成了包括leptosidin在内的Aurones，总产率为5-36%。B 环中带有 3,4-二羟基的查耳酮、黄烷酮、黄酮醇和橙酮均表现出较高的抗氧化活性。此外，B环上带有2,4-二羟基的查耳酮、黄烷酮、黄酮醇和橙酮均表现出优异的美白能力。