(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,6-dimethoxyphenyl)prop-2-en-1-one

• 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: (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,6-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-3-(2,6-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one；(E)-3-(2,6-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: ZCBBKYSIMWEHKK-MDZDMXLPSA-N

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：

  (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,6-dimethoxyphenyl)prop-2-en-1-one 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以30%的产率得到2-(2,6-Dimethoxy-phenyl)-7-methoxy-chroman-4-one
  参考文献：
  名称：

  摘要：

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.

  DOI：

  10.1023/a:1014490817731
• 作为产物：
  描述：

  丹皮酚 、 2,6-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以100%的产率得到(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,6-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  甲氧基化的2'-羟基查耳酮作为抗寄生虫命中化合物

  摘要：

  查耳酮具有广泛的药理活性。在此，合成了一系列的2'-羟基甲氧基化查耳酮，并对其进行了布鲁氏锥虫，克氏锥虫和婴儿利什曼原虫的评价。在合成文库中，化合物1、3、4、7和8是最有效和最具选择性的抗T蛋白。布氏化合物（EC 50  = 1.3-4.2μM，选择性指数> 10倍）。化合物4表现出最好的早期毒性和抗寄生虫特性。使用羟丙基-β-环糊精制剂对BALB / c小鼠进行化合物4的药代动力学研究表明，口服生物利用度提高了7.5倍。

  DOI：

  10.1016/j.ejmech.2016.12.017

文献信息

• Synthesis and Cytotoxic Evaluation of Alkoxylated Chalcones
  作者：Xiao-Guang Bai、Chang-Liang Xu、Shuang-Shuang Zhao、Hong-Wei He、Yu-Cheng Wang、Ju-Xian Wang

  DOI：10.3390/molecules191117256

  日期：——

  A series of chalcones a1–20 bearing a 4-OMe groups on the A-ring were initially synthesized and their anticancer activities towards HepG2 cells evaluated. Subsequently, a series of chalcones b1–42 bearing methoxy groups at the 2' and 6'-positions of the B-ring were synthesized and their anticancer activities towards five human cancer cell lines (HepG2, HeLa, MCF-7, A549 and SW1990) and two non-tumoral human cell lines evaluated. The results showed that six compounds (b6, b8, b11, b16, b18, b22, b23 and b29) displayed promising activities, with compounds b22 and b29 in particular showing higher levels of activity than etoposide against all five cancer cell lines. Compound b29 showed a promising SI value compared with both HMLE and L02 (2.1–6.5 fold in HMLE and > 33 > 103.1 fold in L02, respectively).

  一系列在A环上带有4-OMe基团查尔酮a1-20被合成，并评估了它们对HepG2细胞的抗癌活性。随后，合成了一系列在B环的2'和6'-位置带有甲氧基的查尔酮b1-42，并评估了它们对五种人癌细胞系（HepG2、HeLa、MCF-7、A549和SW1990）和两种非瘤人细胞系的抗癌活性。结果显示，六个化合物（b6、b8、b11、b16、b18、b22、b23和b29）显示出有望的活性，特别是化合物b22和b29在所有五种癌细胞系中显示出比依托泊苷更高的活性水平。与HMLE和L02相比，化合物b29显示出有希望的SI值（分别是HMLE的2.1-6.5倍，L02的>103.1倍）。
• Antimitotic and Antiproliferative Activities of Chalcones: Forward Structure–Activity Relationship
  作者：Ahcène Boumendjel、Julien Boccard、Pierre-Alain Carrupt、Edwige Nicolle、Madeleine Blanc、Annabelle Geze、Luc Choisnard、Denis Wouessidjewe、Eva-Laure Matera、Charles Dumontet

  DOI：10.1021/jm0708331

  日期：2008.4.1

  A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of I I human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.