2'-hydroxy-3-methoxyflavone | 105827-34-7

• 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'-hydroxy-3-methoxyflavone
• 英文别名: 2-(2-hydroxyphenyl)-3-methoxy-4H-chromen-4-one；2-(2-Hydroxyphenyl)-3-methoxy-4H-1-benzopyran-4-one；2-(2-hydroxyphenyl)-3-methoxychromen-4-one
• CAS: 105827-34-7
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: GMVNPWNYMHIQDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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

• 作为产物：
  描述：

  2-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'-hydroxy-3-methoxyflavone
  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

• Wymann, Walter E.; Davis, Roman; Patterson, John W., Synthetic Communications, 1988, vol. 18, # 12, p. 1379 - 1384
  作者：Wymann, Walter E.、Davis, Roman、Patterson, John W.、Pfister, Juerg R.

  DOI：——

  日期：——
• WYMANN, WALTER E.;DAVIS, ROMAN;PATTERSON, JOHN W. (JR);PFISTER, JURG R., SYNTH. COMMUN., 18,(1988) N 12, C. 1379-1384
  作者：WYMANN, WALTER E.、DAVIS, ROMAN、PATTERSON, JOHN W. (JR)、PFISTER, JURG R.

  DOI：——

  日期：——
• US5626883A
  申请人：——

  公开号：US5626883A

  公开（公告）日：1997-05-06
• [EN] ASCORBIC ACID COMPOSITION PROVIDING ENHANCED HUMAN IMMUNE SYSTEM ACTIVITY<br/>[FR] COMPOSITION A BASE D'ACIDE ASCORBIQUE RENFORÇANT L'ACTIVITE DU SYSTEME IMMUNITAIRE CHEZ L'HOMME
  申请人：METAGENICS, INC.

  公开号：WO1995028084A1

  公开（公告）日：1995-10-26

  (EN) A vitamin C supplement comprising ascorbic acid, ascorbyl palmitate, niacinamide ascorbate, calcium ascorbate, magnesium ascorbate, potassium ascorbate, and sodium ascorbate which together can be administered to a human to avoid the transitory initial suppression of human NK cell activity which is present when ascorbic acid alone is administered. Also included are xylitol, lysine acetate, tetrasodium pyrophosphate, ribose, cysteine, and hesperidin which further prolong the biological activity of ascorbic acid and promote the uptake of ascorbic acid by human tissue.(FR) Complément à base de vitamine C comprenant de l'acide ascorbique, du palmitate d'ascorbyle, de l'ascorbate de niacinamide, de l'ascorbate de calcium, de l'ascorbate de magnésium, de l'ascorbate de potassium et de l'ascorbate de sodium qui peuvent être administrés à l'homme pour empêcher la suppression transitoire initiale de l'activité de la cellule NK comme c'est le cas lorsque l'acide ascorbique est administré seul. Ledit complément contient, en outre, du xylitol, de l'acétate de lysine, du pyrophosphate tétrasodique, du ribose, de la cystéine et de l'hespéridine qui prolongent l'activité biologique de l'acide ascorbique et favorisent son absorption par les tissus humains.