2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one | 111391-31-2

• 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: 2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one
• 英文别名: 2-(4-hydroxyphenyl)-3-methoxychromen-4-one
• CAS: 111391-31-2
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: CDQGCHBSQIWYES-UHFFFAOYSA-N

物化性质

• 熔点：
  230-233 °C
• 沸点：
  464.0±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one 生成 2-(4-acetoxy-phenyl)-3-methoxy-chromen-4-one
  参考文献：
  名称：

  花青素。第一部分：选择性甲基化和去甲基化

  摘要：

  DOI：

  10.1039/jr9540004065
• 作为产物：
  描述：

  4-苄氧基苯甲醛 在 palladium 10% on activated carbon 、 氢气 、 双氧水 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 丙酮 为溶剂， 反应 1.0h， 生成 2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells

  摘要：

  Flavonoids are naturally occurring polyphenolic compounds and are among the most promising anticancer agents. A series of flavonols and their 3-methyl ether derivatives were synthesized and assessed for cytotoxicity. It was found that 3'-hydroxy-3,4'-dimethoxyflavone (flavonoid 7a) displayed strong cytotoxicity against human SK-MEL-1 melanoma cells and blocked tubulin polymerization, but had no significant cytotoxic effects against quiescent or proliferating human peripheral blood mononuclear cells. Our analyses showed that flavonoid 7a induces G2-M cell cycle arrest and apoptosis in melanoma cells which is associated with cytochrome c release and activation of both extrinsic and intrinsic apoptotic pathways of cell death. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.09.043

文献信息

• A Structure Activity Relationship Study of 3,4’-Dimethoxyflavone for ArlRS Inhibition in Staphylococcus aureus
  作者：Alexander Weig、Patrick O'Connor、Jakub M. Kwiecinski、Orry Marciano、Angelica Nunag、Andrew Guitierrez、Roberta Melander、Alexander Horswill、Christian Melander

  DOI：10.1039/d3ob00123g

  日期：——

  Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) are difficult to treat due to their resistance to many -lactam antibiotics, and their highly coordinated excretion of virulence factors. One way in...

  耐甲氧西林金黄色葡萄球菌（MRSA）引起的感染很难治疗，因为它们对许多  内酰胺类抗生素都有耐药性，而且毒性因子的排泄高度协调。其中一种方法是...
• Compositions thérapeutiques à base de dérivés de 3-alkoxyflavones et nouveaux dérivés de 3-alkoxyflavones
  申请人：INSTITUT PASTEUR

  公开号：EP0233105A1

  公开（公告）日：1987-08-19

  La présente invention concerne des compositions thérapeutiques à base de dérivés de 3-alkoxy-flavones, ayant notamment une activité antivirale.

  本发明涉及基于 3-烷氧基-黄酮衍生物的治疗组合物，特别是具有抗病毒活性的组合物。
• Flavonoid Dimers as Novel, Potent Antileishmanial Agents
  作者：Iris L. K. Wong、Kin-Fai Chan、Tak Hang Chan、Larry M. C. Chow

  DOI：10.1021/jm301172v

  日期：2012.10.25

  The present study found that synthetic flavonoid dimers with either polyethylene glycol linker or amino ethyleneglycol linker have marked leishmanicidal activity. Compound 39 showed very consistent and promising leishmanicidal activity for both extracellular promastigotes (IC50 ranging from 0.13 to 0.21 mu M) and intracellular amastigotes (IC50 = 0.63 mu M) irrespective of the drug-sensitivity of parasites. Moreover, compound 39 displayed no toxicity toward macrophage RAW 264.7 cells (IC50 > 100 mu M) and primary mouse peritoneal elicited macrophages (IC50 > 88 mu M). Its high value of therapeutic index (> 140) was better than other highly potent antileishmanials such as amphotericin B (therapeutic index = 119). Compound 39 is therefore a new, safe, and effective antileishmanial candidate compound which is even effective against drug-refractory parasites.
• 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
  作者：Nadine De Meyer、Achiel Haemers、Lallan Mishra、Hrishi Kesh Pandey、L. A. C. Pieters、Dirk A. Vanden Berghe、Arnold J. Vlietinck

  DOI：10.1021/jm00106a039

  日期：1991.2

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.
• VANDEN, BERGHE DRIK A.;VLIETINCK, ARNOLD J.;HAEMERS, ACHIEL
  作者：VANDEN, BERGHE DRIK A.、VLIETINCK, ARNOLD J.、HAEMERS, ACHIEL

  DOI：——

  日期：——