Acetic acid 7-acetoxy-2-(4-acetoxy-phenyl)-3,6,8-trimethoxy-4-oxo-4H-chromen-5-yl ester | 57393-69-8

• 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: Acetic acid 7-acetoxy-2-(4-acetoxy-phenyl)-3,6,8-trimethoxy-4-oxo-4H-chromen-5-yl ester
• 英文别名: [4-(5,7-Diacetyloxy-3,6,8-trimethoxy-4-oxochromen-2-yl)phenyl] acetate；[4-(5,7-diacetyloxy-3,6,8-trimethoxy-4-oxochromen-2-yl)phenyl] acetate
• CAS: 57393-69-8
• 化学式: C₂₄H₂₂O₁₁
• 分子量: 486.432
• InChiKey: WBOSFDVOXKUHIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4,5,7-三羟基3,6,8-三甲氧基黄酮 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 生成 Acetic acid 7-acetoxy-2-(4-acetoxy-phenyl)-3,6,8-trimethoxy-4-oxo-4H-chromen-5-yl ester
  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

文献信息

• Cytotoxic and anti-HIV-1 constituents of Gardenia obtusifolia and their modified compounds
  作者：Patoomratana Tuchinda、Wilart Pompimon、Vichai Reutrakul、Manat Pohmakotr、Chalobon Yoosook、Natedao Kongyai、Samaisukh Sophasan、Kulawee Sujarit、Suchart E Upathum、Thawatchai Santisuk

  DOI：10.1016/s0040-4020(02)00999-7

  日期：2002.9

  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.