4H-1-苯并吡喃-4-酮,5-羟基-2-(3-羟基-4-甲氧苯基)-3,6,7,8-四甲氧基- | 102673-80-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 4H-1-苯并吡喃-4-酮,5-羟基-2-(3-羟基-4-甲氧苯基)-3,6,7,8-四甲氧基-
• 英文名称: 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxy-flavone
• 英文别名: 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone；5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7,8-tetramethoxychromen-4-one
• CAS: 102673-80-3
• 化学式: C₂₀H₂₀O₉
• 分子量: 404.373
• InChiKey: GVLMRDDSMVCWKB-UHFFFAOYSA-N

物化性质

• 熔点：
  171.6-172.2 °C
• 沸点：
  660.7±55.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 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：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 4H-1-苯并吡喃-4-酮,5-羟基-2-(3-羟基-4-甲氧苯基)-3,6,7,8-四甲氧基- 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3,5,6,7,8,3',4'-七甲氧基黄酮
  参考文献：
  名称：

  Cytotoxic and anti-HIV-1 constituents of Gardenia obtusifolia and their modified compounds

  摘要：

  5alpha-Cycloart-24-ene-3,23-dione (1), 5alpha-cycloart-24-ene-3,16,23-trione (2) and methyl 3,4-seco-cycloart-4(28),24-diene-29-hydroxy-23-oxo-3-oate (3), together with five known flavones 5,7,4'-tlihydroxy-3,8-dimethoxyflavone (4), 5,7,4'-trihydroxy-3,8,3'-trimethoxyflavone (5), 5,7,4'-trihydroxy-3,6,8-trimethoxyflavone (6), 5,4'-dihydroxy-3,6,7,8-tetramethoxyflavone (7) and 5,3-dihydroxy-3,6,7,8,4'-pentamethoxyflavone (8) have been isolated from the leaves and twigs of Gardenia obtusifolia. The structures were assigned on the basis of spectroscopic methods. Compounds 3-8 and some of the modified compounds showed significant cytotoxic activities in several mammalian cell lines, especially 8 and its diacetate 21 which exhibited potent cytotoxicities (compound 8: P-388 0.05 mug/mL, KB 0.09 mug/mL, BCA-1 0.63 mug/mL, Lu-1 0.09 mug/mL, ASK 0.70 mug/mL; its diacetate: P-388 0.27 mug/mL, KB 0.06 mug/mL, BCA-1 0.53 mug/mL, Lu-1 0.49 mug/mL). It was also found that 5, 8 and 21 showed antimitotic acitivity in the ASK assay. Compounds 2, 4, 6, 7 and some of the modified compounds displayed interesting anti-HIV activity in the syncytium assay, but were inactive or exhibited weak activity in the HIV-1 RT assay; while compound 3 was found to be active in the HIV-1 RT assay (99.9% inhibition at 200 mug/mL), but cytotoxic in the syncytium assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00999-7
• 作为产物：
  描述：

  4-甲氧基-3-苯基甲氧基苯甲酰氯 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢氧化钾 、 aluminum tri-bromide 、 硫酸 、 氢气 、 二甲基二环氧乙烷 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 丙酮 、 乙腈 为溶剂， 反应 20.0h， 生成 4H-1-苯并吡喃-4-酮,5-羟基-2-(3-羟基-4-甲氧苯基)-3,6,7,8-四甲氧基-
  参考文献：
  名称：

  Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XIX. A Convenient Method for Synthesizing 3,5,6,7,8-Pentaoxygenated Flavones.

  摘要：

  由 2'，5'-二羟基-3'，4'，6'-三甲氧基苯乙酮衍生的 6-羟基-5，7，8-三甲氧基黄酮的甲氧基甲基醚经二甲基二氧环己烷氧化得到相应的 3-羟基黄酮。研究了 3-羟基黄酮的选择性 O-烷基化和脱烷基化，并建立了合成以下十种 3、5、6、7、8-五氧根黄酮的简便方法：3-羟基-5，6，7，8-四甲氧基黄酮、3，5-二羟基-6，7，8-三甲氧基黄酮、3，6-二羟基-5，7，8-三甲氧基黄酮、3，5，6-三羟基-7，8-二甲氧基黄酮、3，5，6，7-四羟基-8-甲氧基黄酮及其 3-甲基醚。此外，还合成了 3, 5, 8-三羟基-4', 6, 7-三甲氧基黄酮、3, 8-二羟基-4', 5, 6, 7-四甲氧基黄酮和 5, 8-二羟基-3, 6, 7-三甲氧基黄酮，并研究了它们的光谱特性。此外，还对三种天然黄酮的拟议结构进行了修订。

  DOI：

  10.1248/cpb.43.2054

文献信息

• Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin
  作者：Guy Lewin、Alexandre Maciuk、Sylviane Thoret、Geneviève Aubert、Joëlle Dubois、Thierry Cresteil

  DOI：10.1021/np100065v

  日期：2010.4.23

  Semisynthesis of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone (1), a natural flavone that binds with high affinity to tubulin, was performed from hesperidin, the very abundant Citrus flavanone, by a five-step sequence. The last step of the synthesis also gave rise to 5,3'-dihydroxy-3,6,7,4'-tetramethoxyflavone (= casticin or vitexicarpin) (10), 5,3'-dihydroxy-3,7,8,4'-tetramethoxyflavone (= gossypetin 3,7,8,4'-tetramethyl ether) (11), and, unexpectedly, 5,7,3'-trihydroxy-3,6,8,4'tetramethoxyflavone (12) and 5,3'-dihydroxy-8-dimethylamino-3,6,7,4'-tetramethoxyflavone (= 8-dimethylaminocasticin) (13). Cytotoxicity and antitubulin activity of these five flavones, as well as 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (= ayanin) (14) and intermediate 6,8-dibromo-ayanin (8), were evaluated. Comparison of the responses confirmed and clarified the influence of the A-ring substitution pattern on the biological activity.
• 2-ARYL-NAPHTHYRIDIN-4-ONES AS ANTITUMOR AGENTS
  申请人：The University of North Carolina at Chapel Hill

  公开号：EP0971921A1

  公开（公告）日：2000-01-19
• US5994367A
  申请人：——

  公开号：US5994367A

  公开（公告）日：1999-11-30
• US6071930A
  申请人：——

  公开号：US6071930A

  公开（公告）日：2000-06-06
• US6229016B1
  申请人：——

  公开号：US6229016B1

  公开（公告）日：2001-05-08