7,8-二乙酰氧基-4-苯基香豆素 | 24258-37-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 中文名称: 7,8-二乙酰氧基-4-苯基香豆素
• 英文名称: 7,8-diacetoxy-4-phenylcoumarin
• 英文别名: 7,8-diacetoxy-4-phenyl-coumarin；7,8-Diacetoxy-4-phenyl-cumarin；4-Phenyl-7,8-diacetoxy-cumarin；2H-1-Benzopyran-2-one, 7,8-bis(acetyloxy)-4-phenyl-；(8-acetyloxy-2-oxo-4-phenylchromen-7-yl) acetate
• CAS: 24258-37-5
• 化学式: C₁₉H₁₄O₆
• mdl: MFCD02059562
• 分子量: 338.317
• InChiKey: VDUFUJLCMJJEFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,8-二乙酰氧基-4-苯基香豆素 在 硫酸 作用下， 生成 7,8-二羟基-4-苯基香豆素
  参考文献：
  名称：

  Bargellini; Leonardi, Gazzetta Chimica Italiana, 1911, vol. 41 I, p. 743

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 吡啶 、 4-二甲氨基吡啶 、 磷酸 作用下， 生成 7,8-二乙酰氧基-4-苯基香豆素
  参考文献：
  名称：

  Mechanism of biochemical action of substituted 4-methylcoumarins. Part 11: Comparison of the specificities of acetoxy derivatives of 4-methylcoumarin and 4-phenylcoumarin to acetoxycoumarins: protein transacetylase

  摘要：

  Our earlier observations led to the identification of a microsomal enzyme termed as acetoxy drug: protein transacetylase (TAase) catalyzing the transfer of acetyl groups from acetylated polyphenols to the receptor proteins. TAase was conveniently assayed by the irreversible inhibition of cytosolic glutathione S-transferase (GST) by the model acetoxycoumarin, 7,8-diacetoxy-4-methylcoumarin (1). The specificities of the acetoxy group on the benzenoid ring and position of the pyran carbonyl group of the coumarin with respect to oxygen heteroatom for the catalytic activity of TAase were also reported earlier. In this communication, we have demonstrated that the acetoxy coumarins and acetoxy dihydrocoumarins having a methyl group instead of a phenyl ring at the C-4, when used as the substrates, resulted in enhancement of TAase activity, while the saturation of double bond at C-3 and C-4 position had no effect on TAase activity. A comparison of the optimized structures of 1 and 7,8-diacetoxy-4-phenylcoumarin (2) suggested that the observed influence may be due to out of plane configuration of the phenyl ring at C-4. Further, the TAase-catalyzed activation of NADPH cytochrome c reductase and inhibition of aflatoxin B-1 (AFB(1))-DNA binding by acetoxy 4-phenylcoumarins and dihydrocournarins were significantly lower as compared to those caused by acetoxy 4-methylcoumarins. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.023

文献信息

• An efficient ZrCl4 catalyzed one-pot solvent free protocol for the synthesis of 4-substituted coumarins
  作者：G.V.M. Sharma、J. Janardhan Reddy、P. Sree Lakshmi、P. Radha Krishna

  DOI：10.1016/j.tetlet.2005.06.166

  日期：2005.9

  A versatile and efficient route to 4-substituted cournarins via a Pechmann reaction using ZrCl4 as the catalyst (10 mol %) is described. This method provides several advantages over alternative procedures such as mild, solvent-free conditions at ambient temperature, and direct isolation of the products in high yields. (c) 2005 Published by Elsevier Ltd.
• Canter; Martin; Robertson, Journal of the Chemical Society, 1931, p. 1878
  作者：Canter、Martin、Robertson

  DOI：——

  日期：——
• v. Kostanecki; Weber, Chemische Berichte, 1893, vol. 26, p. 2907
  作者：v. Kostanecki、Weber

  DOI：——

  日期：——
• Bargellini; Leonardi, Gazzetta Chimica Italiana, 1911, vol. 41 I, p. 743
  作者：Bargellini、Leonardi

  DOI：——

  日期：——
• Mechanism of biochemical action of substituted 4-methylcoumarins. Part 11: Comparison of the specificities of acetoxy derivatives of 4-methylcoumarin and 4-phenylcoumarin to acetoxycoumarins: protein transacetylase
  作者：Ajit Kumar、Brajendra K. Singh、Rahul Tyagi、Sapan K. Jain、Sunil K. Sharma、Ashok K. Prasad、Hanumantharao G. Raj、Ramesh C. Rastogi、Arthur C. Watterson、Virinder S. Parmar

  DOI：10.1016/j.bmc.2005.04.023

  日期：2005.7

  Our earlier observations led to the identification of a microsomal enzyme termed as acetoxy drug: protein transacetylase (TAase) catalyzing the transfer of acetyl groups from acetylated polyphenols to the receptor proteins. TAase was conveniently assayed by the irreversible inhibition of cytosolic glutathione S-transferase (GST) by the model acetoxycoumarin, 7,8-diacetoxy-4-methylcoumarin (1). The specificities of the acetoxy group on the benzenoid ring and position of the pyran carbonyl group of the coumarin with respect to oxygen heteroatom for the catalytic activity of TAase were also reported earlier. In this communication, we have demonstrated that the acetoxy coumarins and acetoxy dihydrocoumarins having a methyl group instead of a phenyl ring at the C-4, when used as the substrates, resulted in enhancement of TAase activity, while the saturation of double bond at C-3 and C-4 position had no effect on TAase activity. A comparison of the optimized structures of 1 and 7,8-diacetoxy-4-phenylcoumarin (2) suggested that the observed influence may be due to out of plane configuration of the phenyl ring at C-4. Further, the TAase-catalyzed activation of NADPH cytochrome c reductase and inhibition of aflatoxin B-1 (AFB(1))-DNA binding by acetoxy 4-phenylcoumarins and dihydrocournarins were significantly lower as compared to those caused by acetoxy 4-methylcoumarins. (c) 2005 Elsevier Ltd. All rights reserved.