卡来可黄素 | 481-52-7

• 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: 卡来可黄素
• 英文名称: calycopterin
• 英文别名: 5,4'-dihydroxy-3,6,7,8-tetramethoxyflavone；Calcycopterin；5-hydroxy-2-(4-hydroxyphenyl)-3,6,7,8-tetramethoxychromen-4-one
• CAS: 481-52-7
• 化学式: C₁₉H₁₈O₈
• 分子量: 374.347
• InChiKey: PIUSRRUXGNYCSS-UHFFFAOYSA-N

物化性质

• 熔点：
  226-228 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  639.5±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：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  卡来可黄素 在 10% palladium on activated charcoal 、 氢气 、 硝酸 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 11.4h， 生成 3'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone
  参考文献：
  名称：

  Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.

  摘要：

  Eighteen new analogues of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxy-flavone, a potent natural cytotoxic and antimitotic flavone, were synthesized from calycopterin, the major flavonoid of Calycopteris floribunda Lamk., a traditional Asian medicinal plant. One of them, the 3'-amino substituted analogue, displayed almost the same activity as the reference compound. Pharmacomodulation at C-3' on the B-ring, and at C-5,6,7 and 8 on the A-ring allowed to refine structure-activity relationships within the cytotoxic flavones series. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.035
• 作为产物：
  描述：

  2-hydroxy-3,4,5,6,ο-pentamethoxyacetophenone 在 potassium-<4-benzoyloxy benzoate> 、 氢溴酸 、 溶剂黄146 作用下， 生成 卡来可黄素
  参考文献：
  名称：

  5∶6∶7∶8-hydroxy-flavonols

  摘要：

  DOI：

  10.1007/bf03171070

文献信息

• Seshadri; Venkateswarlu, Proceedings - Indian Academy of Sciences, Section A, 1946, # 23, p. 192,200
  作者：Seshadri、Venkateswarlu

  DOI：——

  日期：——
• Über einen neuen Flavonfarbstoff
  作者：Walter Karrer

  DOI：10.1002/hlca.193401701198

  日期：——
• 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.
• OGANESYAN, G. B.;MNATSAKANYAN, V. A.;GACH-BAJTTS, EH., ARM. XIM. ZH., 42,(1989) N1, S. 717-724
  作者：OGANESYAN, G. B.、MNATSAKANYAN, V. A.、GACH-BAJTTS, EH.

  DOI：——

  日期：——
• Shah et al., Journal of the Indian Chemical Society, 1942, vol. 19, p. 135,137
  作者：Shah et al.

  DOI：——

  日期：——