7-hydroxy-3’,4’,5,6,8-pentamethoxyflavone | 149402-88-0

• 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: 7-hydroxy-3’,4’,5,6,8-pentamethoxyflavone
• 英文别名: 7-hydroxy-5,6,8,3′,4′-pentamethoxyflavone；7-hydroxy-3',4',5,6,8-pentamethoxyflavone；7-hydroxy-5,6,8,3',4'-pentamethoxyflavone；7-O-demethylnobiletin；7-desmethyl nobiletin；7-demethylnobiletin；2-(3,4-Dimethoxyphenyl)-7-hydroxy-5,6,8-trimethoxy-4H-1-benzopyran-4-one；2-(3,4-dimethoxyphenyl)-7-hydroxy-5,6,8-trimethoxychromen-4-one
• CAS: 149402-88-0
• 化学式: C₂₀H₂₀O₈
• 分子量: 388.374
• InChiKey: XGOWVPRWNRKCSL-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  190-191°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3’,4’,5,6,8-pentamethoxyflavone 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 5.0h， 生成 去甲基川陈皮素
  参考文献：
  名称：

  Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells

  摘要：

  A series of polymethoxyflavonoids (3-16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 mu M).

  DOI：

  10.1007/s00044-017-1871-4
• 作为产物：
  描述：

  地奥司明 在 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 、 copper(I) bromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 7-hydroxy-3’,4’,5,6,8-pentamethoxyflavone
  参考文献：
  名称：

  Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells

  摘要：

  A series of polymethoxyflavonoids (3-16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 mu M).

  DOI：

  10.1007/s00044-017-1871-4

文献信息

• Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives
  作者：Tomohiro Asakawa、Hiroto Sagara、Masaki Kanakogi、Aiki Hiza、Yuta Tsukaguchi、Takahiro Ogawa、Miho Nakayama、Hitoshi Ouchi、Makoto Inai、Toshiyuki Kan

  DOI：10.1021/acs.oprd.9b00091

  日期：2019.4.19

  We present a practical synthesis of the polymethoxylated citrus flavone nobiletin that is suitable for use on a hundred gram scale. Ready availability of this compound and its derivatives will aid detailed chemical-biological investigations of their biological activities, including activation of signaling via the cAMP-dependent protein kinase A/extracellular signal-related protein kinase/cAMP response

  我们提出了适用于一百克规模的聚甲氧基化柑桔黄酮Nobiletin的实用合成方法。该化合物及其衍生物的现成可用性将有助于对其生物学活性的详细化学生物学研究，包括通过cAMP依赖性蛋白激酶A /细胞外信号相关蛋白激酶/ cAMP反应元件结合蛋白途径激活信号。
• Analysis of Fluorescence Spectra of Citrus Polymethoxylated Flavones and Their Incorporation into Mammalian Cells
  作者：Danielle R. Gonçalves、John A. Manthey、Paulo I. da Costa、Marilia C. M. Rodrigues、Thais B. Cesar

  DOI：10.1021/acs.jafc.8b02052

  日期：2018.7.18

  compounds. An innate attribute of PMFs is their ultraviolet-light-induced fluorescence, and the fluorescence spectra of 14 PMFs and 7 PMF metabolites were measured in methanol. These spectra were shown to be strongly influenced by the compounds’ hydroxy and methoxy substituents. For a subset of these compounds, the fluorescence spectra were measured when bound to human carcinoma Huh7.5 cells. Emission-wavelength

  柑橘类聚甲氧基黄酮（PMF）影响人类疾病中的生化级联反应，但对于这些化合物如何与细胞相互作用以及这些缔合如何影响这些化合物的作用知之甚少。PMF的固有属性是其紫外线诱导的荧光，并且在甲醇中测量了14种PMF和7种PMF代谢物的荧光光谱。这些光谱显示出受化合物的羟基和甲氧基取代基的强烈影响。对于这些化合物的一个子集，当与人类癌细胞Huh7.5细胞结合时，测量了荧光光谱。带有游离羟基取代基的PMF代谢物的最大发射波长在与Huh7.5细胞结合时表现出70-80 nm的红移。几乎所有这些化合物都观察到水对溶剂的显着影响，
• Concise synthesis of polymethoxyflavone sudachitin and its derivatives, and biological evaluations
  作者：Hiroto Sagara、Masaki Kanakogi、Yuki Tara、Hitoshi Ouchi、Junko Kimura、Yukiko Kaneko、Makoto Inai、Tomohiro Asakawa、Tomohisa Ishikawa、Toshiyuki Kan

  DOI：10.1016/j.tetlet.2018.03.064

  日期：2018.5

  We accomplished a divergent synthesis of sudachitin (2), a polymethoxyflavone isolated from citrus fruits, and six derivatives from acetophenone 9, which was an intermediate in our previous synthesis of nobiletin (1). Compound 2 enhanced glucose-induced insulin secretion in INS-1D cells, but was less potent than 1. Compared with 1, compound 2 and two derivatives were more potent inhibitors of cAMP-specific phosphodiesterase. (C) 2018 Published by Elsevier Ltd.
• Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells
  作者：Van-Son Nguyen、Wei Li、Yue Li、Qiuan Wang

  DOI：10.1007/s00044-017-1871-4

  日期：2017.7

  A series of polymethoxyflavonoids (3-16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 mu M).