4-benzyloxy-2'-hydroxy-3,4'-dimethoxychalcone | 95560-60-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-benzyloxy-2'-hydroxy-3,4'-dimethoxychalcone
• 英文别名: 3-<4-Benzyloxy-3-methoxy-phenyl>-1-<2-hydroxy-4-methoxy-phenyl>-prop-2-en-1-on；4-Benzyloxy-2'-hydroxy-3,4'-dimethoxychalcone；1-(2-hydroxy-4-methoxyphenyl)-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 95560-60-4
• 化学式: C₂₄H₂₂O₅
• 分子量: 390.436
• InChiKey: RZFPNYSXHIVVOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-2'-hydroxy-3,4'-dimethoxychalcone 在 双氧水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 生成 2-[4-(benzyloxy)-3-methoxyphenyl]-3-hydroxy-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction

  摘要：

  Chrysosplenol C (4',5,6-trihydroxy-3,3',7-tri-methoxyflavone) isolated from Miliusa balansae has unique structural features as a reversible inotropic agent independent of beta-adrenergic signaling and with selective activation of cardiac myosin ATPase. Hence, a series of chrysosplenol analogues were synthesized and explored for identification of pharmacophore that is essential for the increasing contractility in rat ventricular myocytes. Analogue 7-chloro-2-(3-hydroxypheny1)-3-methoxy-4H-chromen-4-one showed highly potent contractility (54.8% at 10 mu M) through activating cardiac myosin ATPase (38.7% at 10 mu M). Our systematic structure activity relationship study revealed that flavonoid nucleus of chrososplenol C appears to be an essential basic skeleton and hydrophobic substituent at position 7 of chromenone such as methoxy or chloro enhances the activity. Additionally, our ATPase study suggested that these chrysosplenol analogues have selectivity toward cardiac myosin activation. Thus, the novel flavonone with 3-/7-hydrophobic substituent and 3'-hydrogen bonding donor function is a novel scaffold for discovery of a new positive inotropic agent.

  DOI：

  10.1021/acsmedchemlett.5b00043
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.33h， 生成 4-benzyloxy-2'-hydroxy-3,4'-dimethoxychalcone
  参考文献：
  名称：

  Velutin及其类似物的抗黑色素生成特性

  摘要：

  Velutin是天然植物中的一种黄酮，具有多种有益的活性，例如美白皮肤，以及抗炎，抗过敏，抗氧化和抗菌活性。但是，尚未研究velutin的结构与其抗黑素生成活性之间的关系。在这项研究中，我们通过化学合成获得了12种维他汀衍生物，这些化合物在黄酮骨架的C5，C7，C3'和C4'处被氢，羟基和甲氧基官能团取代，以进行维他汀结构类似物的SAR分析。SAR研究表明，黄酮骨架的C5，C7，C3'和C4'处的官能团取代会影响与黑色素合成有关的生物学活性。羟基和甲氧基在C5和C7位置的共存对于抑制酪氨酸酶活性至关重要。然而，在黄酮骨架的C3'和C4'处取代的1,2-二醇化合物诱导黑素瘤细胞凋亡。此外，在C3'和C4'处被甲氧基或氢取代对于抑制黑色素生成是必不可少的。因此，这项研究将有助于开发天然来源的功能材料，以调节黑色素的合成。

  DOI：

  10.3390/molecules26103033

文献信息

• 3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells
  作者：Francisco Estévez-Sarmiento、Mercedes Said、Ignacio Brouard、Francisco León、Celina García、José Quintana、Francisco Estévez

  DOI：10.1016/j.bmc.2017.09.043

  日期：2017.11

  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.