1-(2-Hydroxy-phenyl)-3-(3-benzyloxy-4-methoxy-phenyl)-prop-2-en-1-on | 77987-66-7

• 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-Hydroxy-phenyl)-3-(3-benzyloxy-4-methoxy-phenyl)-prop-2-en-1-on
• 英文别名: 3-benzyloxy-4-methoxy-2'-hydroxychalcone；(E)-1-(2-hydroxyphenyl)-3-(4-methoxy-3-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 77987-66-7
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: QYADGBNDKLLFIV-ACCUITESSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  556.3±50.0 °C(predicted)
• 密度：
  1.213±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：

  1-(2-Hydroxy-phenyl)-3-(3-benzyloxy-4-methoxy-phenyl)-prop-2-en-1-on 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以90 %的产率得到2-(3-(benzyloxy)-4-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Anti-tyrosinase flavone derivatives and their anti-melanogenic activities: Importance of the β-phenyl-α,β-unsaturated carbonyl scaffold

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106504
• 作为产物：
  描述：

  溴甲苯 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1-(2-Hydroxy-phenyl)-3-(3-benzyloxy-4-methoxy-phenyl)-prop-2-en-1-on
  参考文献：
  名称：

  Anti-tyrosinase flavone derivatives and their anti-melanogenic activities: Importance of the β-phenyl-α,β-unsaturated carbonyl scaffold

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106504

文献信息

• Inhibitory activity of prostaglandin E2 production by the synthetic 2′-hydroxychalcone analogues: Synthesis and SAR study
  作者：Thanh-Dao Tran、Haeil Park、Hyun Pyo Kim、Gerhard F. Ecker、Khac-Minh Thai

  DOI：10.1016/j.bmcl.2009.02.001

  日期：2009.3

  A series of 2'-hydroxychalcones has been synthesized and screened for their in vitro inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells. Structure-activity relationship study suggested that inhibitory activity against prostaglandin E-2 production was governed to a greater extent by the substituent on B ring of the chalcone, and most of the active compounds have at least two methoxy or benzyloxy groups on B ring. The relationship between chalcone structures and their PGE(2) inhibitory activities was also interpreted by docking study on cyclooxygenase-2. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• MEEGAN M. J.; DONELLY D. M. X., J. CHEM. RES. SYNOP., 1981, NO 1, 4 J. CHEM. RES. MICROFICHE, 1981, NO 1-+
  作者：MEEGAN M. J.、 DONELLY D. M. X.

  DOI：——

  日期：——
• 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