[E]-3-(m-methoxy-p-benzyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one | 4537-34-2

• 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: [E]-3-(m-methoxy-p-benzyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 4-benzyloxy-2'-hydroxy-3-methoxy-trans-chalcone；4-Benzyloxy-2'-hydroxy-3-methoxy-trans-chalkon；(E)-1-(2-hydroxyphenyl)-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 4537-34-2
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: GOFLNFZOOOWWAQ-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [E]-3-(m-methoxy-p-benzyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 8.0h， 以64%的产率得到3'-methoxy-4'-benzyloxyflavanone
  参考文献：
  名称：

  De, Mahuya; Majumdar, Dyuti P.; Kundu, Nitya G., Journal of the Indian Chemical Society, 1999, vol. 76, # 11-12, p. 665 - 674

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰氧基-2-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 对甲苯磺酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 48.0h， 生成 [E]-3-(m-methoxy-p-benzyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  De, Mahuya; Majumdar, Dyuti P.; Kundu, Nitya G., Journal of the Indian Chemical Society, 1999, vol. 76, # 11-12, p. 665 - 674

  摘要：

  DOI：

文献信息

• Synthesis of a library of glycosylated flavonols
  作者：Zhitao Li、George Ngojeh、Paul DeWitt、Zhi Zheng、Min Chen、Brendan Lainhart、Vincent Li、Peter Felpo

  DOI：10.1016/j.tetlet.2008.10.032

  日期：2008.12

  products isolated from plants. Some glycosylated flavonols showed very interesting biological activities. A library of flavonols has been made through Algar-Flynn-Oyamada reaction from 2'-hydroxyacetophenones and benzaldehydes. Glycosylation of these flavonols with various glycosyl donors affords a library of glycosylated flavonols. These compounds are potentially useful pharmacologically active compounds

  黄酮醇是从植物中分离出来的一类重要的天然产物。一些糖基化的黄酮醇表现出非常有趣的生物学活性。通过Algar-Flynn-Oyamada反应，由2'-羟基苯乙酮和苯甲醛制得黄酮醇。这些黄酮醇与各种糖基供体的糖基化提供了糖基化黄酮醇的文库。这些化合物可能是有用的药理活性化合物，并将对其生物学活性进行研究。
• Understanding the Cardioprotective Effects of Flavonols: Discovery of Relaxant Flavonols without Antioxidant Activity
  作者：Cheng Xue Qin、Xingqiang Chen、Richard A. Hughes、Spencer J. Williams、Owen L. Woodman

  DOI：10.1021/jm070352h

  日期：2008.3.1

  3 ',4 '-Dihydroxyflavonol (DiOHF) is a cardioprotective flavonol that can reduce injury after myocardial ischemia and reperfusion and thus is a promising small molecule for the treatment of cardiovascular disease. Like all vasoactive flavonols reported to date, DiOHF is both relaxant and antioxidant, hindering investigation of the relative contribution of each activity for the prevention of reperfusion injury. This study investigates structure-activity relationships of variations at the 3 ' and 4 ' positions of the B ring of DiOHF and vasorelaxant and antioxidant activities. Relaxation of rat isolated aortic rings precontracted with KCl revealed that the most active flavonols were those with a 4 '-hydroxyl group, with the opening of potassium channels as a possible contributing mechanism. For the antioxidant activity, with the exception of DiOHF, none of the flavonols investigated were able to significantly scavenge superoxide radical, and none of the three most potent vasorelaxant flavonols could prevent oxidant-induced endothelial dysfunction. The discovery of single-acting vasorelaxant flavonols without antioxidant activity, in particular 4 '-hydroxy-3 '-methoxyflavonol, will assist in investigating the mechanism of flavonol-induced cardioprotection.
• Yamaguchi, Nippon Kagaku Zasshi, 1959, vol. 80, p. 204
  作者：Yamaguchi

  DOI：——

  日期：——
• Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships
  作者：Mauricio Cabrera、Macarena Simoens、Gabriela Falchi、M. Laura Lavaggi、Oscar E. Piro、Eduardo E. Castellano、Anabel Vidal、Amaia Azqueta、Antonio Monge、Adela López de Ceráin、Gabriel Sagrera、Gustavo Seoane、Hugo Cerecetto、Mercedes González

  DOI：10.1016/j.bmc.2007.03.031

  日期：2007.5

  A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity. (c) 2007 Published by Elsevier Ltd.
• Anti-tyrosinase flavone derivatives and their anti-melanogenic activities: Importance of the β-phenyl-α,β-unsaturated carbonyl scaffold
  作者：Jieun Lee、Yeongmu Jeong、Hee Jin Jung、Sultan Ullah、Jeongin Ko、Ga Young Kim、Dahye Yoon、Sojeong Hong、Dongwan Kang、Yujin Park、Pusoon Chun、Hae Young Chung、Hyung Ryong Moon

  DOI：10.1016/j.bioorg.2023.106504

  日期：2023.3