2'-hydroxy-3,4',6'-trimethoxychalcone | 76554-68-2

• 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'-hydroxy-3,4',6'-trimethoxychalcone
• 英文别名: 1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one
• CAS: 76554-68-2
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: AOXAMOYDMUNFNC-UHFFFAOYSA-N

物化性质

• 熔点：
  96.5-97 °C
• 沸点：
  529.9±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-3,4',6'-trimethoxychalcone 在 碘 、 三溴化硼 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 240.5h， 生成 3',5,7-trihydroxyflavone
  参考文献：
  名称：

  Modulation of human neutrophils' oxidative burst by flavonoids

  摘要：

  Inflammation is a normal response towards tissue injury, but may become deleterious to the organism if uncontrolled. The overproduction of reactive species during the inflammatory process may cause or magnify the damage at inflammatory sites. Flavonoids have been suggested as therapeutic agents to avoid such damage, as these compounds exhibit anti-inflammatory activity, through the modulation of oxidative stress and signalling pathways. Both effects may attenuate neutrophils' activities at inflammatory sites. In this study, we investigated the structure/activity relationship of a series of flavonoids on the oxidative burst of human neutrophils in vitro, as a measure of its anti-inflammatory potential. Neutrophils were stimulated with phorbol-12-myristate-13-acetate, and fluorescence and chemiluminescence techniques were used to evaluate the generation of reactive oxygen species. All the tested flavonoids revealed the ability to modulate the neutrophil's oxidative burst. From the obtained results, the pivotal role of the catechol group in the B-ring was evidenced as well as the minor importance of the hydroxylations in the A-ring, which did not appear to be determinant for the activity, although clearly influencing the lipophilicity of the tested flavonoids. It is also clarified the importance of the methylation in the OH group at the B-ring catechol moiety. In conclusion, the obtained results uncover new possible strategies for the resolution of inflammatory processes, using flavonoids to modulate neutrophil's oxidative burst. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.019
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 3-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2'-hydroxy-3,4',6'-trimethoxychalcone
  参考文献：
  名称：

  从手性前体中减员强化的脱氮和绝对不对称合成黄酮

  摘要：

  从溶剂中重结晶后，七个外消旋的5,7-二甲氧基黄酮酮提供了凝聚物晶体。研究了三种方法来实现基于手性团聚体系统动态结晶的不对称转化。第一个是通过减磨增强的去消旋作用使外消旋黄烷酮手性对称性破坏。在碱（1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU））和玻璃珠存在下，外消旋黄烷酮在少量丙醇中的连续悬浮促进了手性对称性的破坏并将黄烷酮转化为晶体具有78％至99％ee的（+）-或（-）-对映体。第二种方法涉及中间体醛醇缩合产物的环化，以产生具有90％ee的旋光性黄烷酮，其中涉及可逆的oxa-Michael加成反应以及减磨作用。

  DOI：

  10.1021/acs.cgd.0c00955

文献信息

• Flavokawains B and C, melanogenesis inhibitors, isolated from the root of Piper methysticum and synthesis of analogs
  作者：Hye-Jin Jeong、Chang Seok Lee、Janggyoo Choi、Yong Deog Hong、Song Seok Shin、Jun Seong Park、John Hwan Lee、Seokyong Lee、Kee Dong Yoon、Jaeyoung Ko

  DOI：10.1016/j.bmcl.2014.12.082

  日期：2015.2

  of Piper methysticum was found to inhibit melanogenesis in MSH-activated B16 melanoma cells. Flavokawains B and C were isolated from this extract based on their anti-melanogenesis activity and found to inhibit melanogenesis with IC50 values of 7.7 μM and 6.9 μM, respectively. Flavokawain analogs were synthesized through a Claisen–Schmidt condensation of their corresponding acetophenones and benzaldehydes

  发现胡椒的根的乙醇提取物抑制了MSH激活的B16黑色素瘤细胞中的黑色素生成。基于它们的抗黑素生成活性，从该提取物中分离出黄酮类固醇B和C，发现抑制黑素生成的IC 50值分别为7.7μM和6.9μM 。Flavokawain类似物是通过其相应的苯乙酮和苯甲醛的Claisen-Schmidt缩合反应合成的，并根据其酪氨酸酶抑制和抗黑色素生成活性进行了评估。在使用MSH激活的B16黑色素瘤细胞的黑色素生成抑制试验中，化合物1b最有效，IC 50值为2.3μM。
• Investigation of Chalcones as Selective Inhibitors of the Breast Cancer Resistance Protein: Critical Role of Methoxylation in both Inhibition Potency and Cytotoxicity
  作者：Glaucio Valdameri、Charlotte Gauthier、Raphaël Terreux、Rémy Kachadourian、Brian J. Day、Sheila M. B. Winnischofer、Maria E. M. Rocha、Véronique Frachet、Xavier Ronot、Attilio Di Pietro、Ahcène Boumendjel

  DOI：10.1021/jm2016528

  日期：2012.4.12

  ABCG2 plays a major role in anticancer-drug efflux and related tumor multidrug resistance. Potent and selective ABCG2 inhibitors with low cytotoxicity were investigated among a series of 44 chalcones and analogues (1,3-diarylpropenones), by evaluating their inhibitory effect on the transport of mitoxantrone, a known ABCG2 substrate. Six compounds producing complete inhibition with IC50 values below 0.5 mu M and high selectivity for ABCG2 were identified. The number and position of methoxy substituents appeared to be critical for both inhibition and cytotoxicity. The best compounds, with potent inhibition and low toxicity, contained an N-methyl-1-indolyl (compound 38) or a 6'-hydroxyl-2',4'-dimethoxy-1-phenyl (compound 27) moiety (A-ring) and two methoxy groups at positions 2 and 6 of the 3-phenyl moiety (B-ring). Methoxy substitution contributed to inhibition at positions 3 and 5, but had a negative effect at position 4. Finally, methoxy groups at positions 3, 4, and 5 of the B-ring markedly increased cytotoxicity and, therefore, should be avoided.