acetic acid 2-oxo-3-phenyl-2H-chromen-7-yl ester | 6296-55-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: acetic acid 2-oxo-3-phenyl-2H-chromen-7-yl ester
• 英文别名: acetic acid 3-phenyl-coumarin-7-yl ester；acetic acid 3-phenylcoumarin-7-yl ester；2-oxo-3-phenyl-2H-chromen-7-yl acetate；7-acetoxy-3-phenyl-2H-chromen-2-one；7-acetoxy-3-phenylchromen-2-one；7-acetoxy-3-phenyl-chromen-2-one；(2-oxo-3-phenylchromen-7-yl) acetate
• CAS: 6296-55-5
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: QWVIHBPMUGBFLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetic acid 2-oxo-3-phenyl-2H-chromen-7-yl ester 在 sodium hydroxide 、 钯 作用下， 生成 3-(2,4-dioxo-cyclohexyl)-2-phenyl-propionic acid
  参考文献：
  名称：

  Reduction of Phenols. New Synthesis of Oxyhexahydro-3-ketophenanthrenes by Cyclodehydration of 4-(β-Arylethyl)-1,3-cyclohexandiones

  摘要：

  DOI：

  10.1021/ja01536a037
• 作为产物：
  描述：

  sodium phenylacetate 、 4-(乙酰基氧基)-2-羟基苯甲醛 在 乙酸酐 作用下， 反应 8.0h， 生成 acetic acid 2-oxo-3-phenyl-2H-chromen-7-yl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of hydroxylated 3-phenylcoumarins as antioxidants and antiproliferative agents

  摘要：

  Based on the observed biological activities of coumarins and resveratrol, we synthesized fourteen hydroxylated 3-phenylcoumarins (stilbene-coumarin hybrids) including six novel ortho-hydroxy-methoxy substituted derivatives, 1-14, by Perkin reaction. We characterized these compounds concerning their antioxidant activity against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced pBR322 DNA strand breakage, and their antiproliferative effects on human promyelocytic leukemia HL-60 and human lung adenocarcinoma epithelial A549 cells. Structure-activity relationship information suggests that the introduction of ortho-hydroxy-methoxy groups and ortho-dihydroxy groups on the aromatic A ring could efficiently improve antiproliferative activity. Interestingly, a new derivative, 6-methoxy-7-hydroxy-3-(4'-hydroxyphenyl)coumarin, 9, behaved as a poor antioxidant but appeared to be the most potent antiproliferative agent among the compounds examined, and this activity was mediated by deregulation in cell cycle and induction of apoptosis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.090

文献信息

• Design and discovery of tyrosinase inhibitors based on a coumarin scaffold
  作者：M. J. Matos、C. Varela、S. Vilar、G. Hripcsak、F. Borges、L. Santana、E. Uriarte、A. Fais、A. Di Petrillo、F. Pintus、B. Era

  DOI：10.1039/c5ra14465e

  日期：——

  A novel series of 3-aryl and 3-heteroarylcoumarins displaying tyrosinase inhibitory activity.

  一部包含对酪氨酸酶抑制活性的3-芳基和3-杂环基香豆素的小说系列。
• Study of Coumarin-Resveratrol Hybrids as Potent Antioxidant Compounds
  作者：Maria Matos、Francisco Mura、Saleta Vazquez-Rodriguez、Fernanda Borges、Lourdes Santana、Eugenio Uriarte、Claudio Olea-Azar

  DOI：10.3390/molecules20023290

  日期：——

  In the present work we synthesized a selected series of hydroxylated 3-phenylcoumarins 5–8, with the aim of evaluating in detail their antioxidant properties. From an in depth study of the antioxidant capacity data (ORAC-FL, ESR, CV and ROS inhibition) it was concluded that these derivatives are very good antioxidants, with very interesting profiles in all the performed assays. The study of the effect of the number and position of the hydroxyl groups on the antioxidant activity was the principal aim of this study. In particular, 7-hydroxy-3-(3'-hydroxy)phenylcoumarin (8) proved to be the most active and effective antioxidant of the selected series in four of the performed assays (ORAC-FL = 11.8, capacity of scavenging hydroxyl radicals = 54%, Trolox index = 2.33 and AI30 index = 0.18). However, the presence of two hydroxyl groups on this molecule did not increase greatly the activity profile. Theoretical evaluation of ADME properties of all the derivatives was also carried out. All the compounds can act as potential candidates for preventing or minimizing the free radical overproduction in oxidative-stress related diseases. These preliminary findings encourage us to perform a future structural optimization of this family of compounds.

  在本研究中，我们合成了一系列选择性的羟基化3-苯基香豆素5-8，旨在详细评估其抗氧化特性。通过对抗氧化能力数据（ORAC-FL、ESR、CV和ROS抑制）的深入研究，我们得出结论，这些衍生物是非常好的抗氧化剂，在所有进行的实验中表现出非常有趣的特征。研究羟基数量和位置对抗氧化活性的影响是本研究的主要目标。特别是，7-羟基-3-(3'-羟基)苯基香豆素（8）被证明是所选系列中在四项实验中最活跃和有效的抗氧化剂（ORAC-FL=11.8，羟基自由基清除能力=54%，Trolox指数=2.33，AI30指数=0.18）。然而，这种分子上两个羟基的存在并没有显著提高活性特征。还对所有衍生物的ADME特性进行了理论评估。所有化合物都可以作为潜在候选者，以防止或减少与氧化应激相关疾病中自由基的过量产生。这些初步发现鼓励我们对这一类化合物进行未来的结构优化。
• Photophysical investigation of 3-substituted 4-alkyl and/or 7-acetoxy coumarin derivatives—A study of the effect of substituents on fluorescence
  作者：Choorikkat Ranjith、K.K. Vijayan、Vakayil K. Praveen、N.S. Saleesh Kumar

  DOI：10.1016/j.saa.2010.02.027

  日期：2010.5

  novel substituted 2H-chromen-2-one (coumarin) derivatives has been subjected to photophysical analysis. Though the influence of the electron-donating groups such as amino, substituted amino, hydroxyl, alkoxy groups, etc. at position 7 of the coumarin ring system has been extensively studied, the luminescent properties of the coumarin moieties with an acetoxy substituent have not been explored. Herein it

  在本工作中，对一系列新型取代的2H-铬-2--2-（香豆素）衍生物进行了光物理分析。尽管已经广泛研究了香豆素环系统的7位上的供电子基团如氨基，取代的氨基，羟基，烷氧基等的影响，但尚未研究具有乙酰氧基取代基的香豆素部分的发光性质。探索。本文试图研究取代的香豆素衍生物的荧光行为随2H-色烯-2-酮骨架上取代基的性质和位置的变化。还简要地描述了在位置4处的甲基取代基对色酮单元施加异常光物理行为的作用。
• Modified coumarins. 29. Synthesis of structural analogs of natural 6-arylfuro[3,2-g]chromen-7-ones
  作者：M. M. Garazd、Ya. L. Garazd、A. S. Ogorodniichuk、V. P. Khilya

  DOI：10.1007/s10600-009-9261-x

  日期：2009.3

  3-Substituted 6-arylfuro[3,2-g]chromen-7-ones, structural analogs of natural furocoumarins, were synthesized by linear annelation of a furan fragment to a 3-arylcoumarin system.

  3-取代的6-芳基呋喃[3,2-g]色烯-7-酮，作为天然呋喃香豆素的结构类似物，通过将呋喃片段线性连接到3-芳基香豆素体系中合成。
• [EN] HYDROPHOBIC COMPOUNDS FOR OPTICALLY ACTIVE DEVICES<br/>[FR] COMPOSÉS HYDROPHOBES POUR DISPOSITIFS OPTIQUEMENT ACTIFS
  申请人：MERCK PATENT GMBH

  公开号：WO2018149855A1

  公开（公告）日：2018-08-23

  The present invention relates to novel compounds, particularly to compounds comprising a photoactive unit, said novel compounds being particularly suitable for compositions and ophthalmic devices as well as to compositions and ophthalmic devices comprising such compounds.

  本发明涉及新型化合物，特别是包含光活性单元的化合物，这些新型化合物特别适用于组合物和眼科器械，以及包含这些化合物的组合物和眼科器械。