7-benzyloxy-4'-methoxyflavone | 132351-73-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-benzyloxy-4'-methoxyflavone
• 英文别名: 7-O-benzyl-4'-methoxyflavone；7-benzyloxy-2-(4-methoxy-phenyl)-chromen-4-one；7-Benzyloxy-2-(4-methoxy-phenyl)-chromen-4-on；7-(benzyloxy)-2-(4-methoxyphenyl)-4H-chromen-4-one；2-(4-methoxyphenyl)-7-phenylmethoxychromen-4-one
• CAS: 132351-73-6
• 化学式: C₂₃H₁₈O₄
• 分子量: 358.394
• InChiKey: AKECFOUZFWPYLS-UHFFFAOYSA-N

物化性质

• 熔点：
  99 °C(Solv: ethanol (64-17-5))
• 沸点：
  544.2±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-4'-methoxyflavone 在 氢溴酸 、 溶剂黄146 作用下， 生成 7,4’-二羟基黄酮
  参考文献：
  名称：

  Mahal et al., Journal of the Chemical Society, 1935, p. 866

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 7-benzyloxy-4'-methoxyflavone
  参考文献：
  名称：

  Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

  摘要：

  A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.087

文献信息

• Solution Phase Synthesis of a Combinatorial Library of Chalcones and Flavones as Potent Cathepsin V Inhibitors
  作者：Joel Alvim、Richele P. Severino、Emerson F. Marques、Ariane M. Martinelli、Paulo C. Vieira、João B. Fernandes、M. Fatima das G. F. da Silva、Arlene G. Corrêa

  DOI：10.1021/cc100076k

  日期：2010.9.13

  Cathepsin V is a papain-like cysteine protease. It is involved in the control of human T cells (responsible for cell immunity), and presents the largest elastolytic activity among the proteolytic enzymes. Therefore, cathepsin V is a potential molecular target for the treatment of atherosclerosis. In the present work, natural flavonoids were screened against cathepsin V, and two flavones were identified

  组织蛋白酶V是一种木瓜蛋白酶样半胱氨酸蛋白酶。它参与人类T细胞的控制（负责细胞免疫），并在蛋白水解酶中表现出最大的弹性。因此，组织蛋白酶V是治疗动脉粥样硬化的潜在分子靶标。在目前的工作中，针对组织蛋白酶V筛选了天然类黄酮，并确定了两种黄酮是组织蛋白酶V的有效抑制剂。基于此结果，在溶液相中使用清道夫试剂制备了查尔酮和黄酮的组合文库，并经过充分评估。
• One-step conversion of flavanones into isoflavones: a new facile biomimetic synthesis of isoflavones
  作者：Takeshi Kinoshita、Koji Ichinose、Ushio Sankawa

  DOI：10.1016/s0040-4039(00)88565-2

  日期：1990.1
• Synthesis of novel 4,6-diaryl-2-aminopyrimidines as potential antiplasmodial agents
  作者：Rajani Giridhar、Riyaj S. Tamboli、Dhaval G. Prajapati、Sanket Soni、Sarita Gupta、M. R. Yadav

  DOI：10.1007/s00044-012-0328-z

  日期：2013.7

  A novel series of 4,6-diaryl-2-aminopyrimidines 8a-o has been synthesized and evaluated for in vitro antiplasmodial activity against Plasmodium falciparum. Out of the 15 compounds synthesized and tested, 6 compounds have shown IC50 values in the range of 1.61-9.53 mu g/mL. These compounds are several times more potent than chloroquine and quinine, the two standard drugs used for the purpose of comparison.
• Dimethylsulfoxide–iodine catalysed deprotection of 2′-allyloxychalcones: synthesis of flavones
  作者：Pradeep D. Lokhande、Sachin S. Sakate、Kiran N. Taksande、Beena Navghare

  DOI：10.1016/j.tetlet.2004.12.041

  日期：2005.2

  A new one-pot method is described for the removal of O-allyl protecting groups under oxidative conditions at neutral pH. 2'-Allyloxychalcones undergo deprotection and subsequent oxidative cyclisation to give flavones. The general applicability of the reagent has been studied. (C) 2005 Published by Elsevier Ltd.
• Parveen, Nazneen; Khan, Nizam U.; Logani, Journal of the Indian Chemical Society, 1997, vol. 74, # 5, p. 419 - 420
  作者：Parveen, Nazneen、Khan, Nizam U.、Logani

  DOI：——

  日期：——