4'-hydroxy-3,6,7,8-tetramethoxy-flavone | 1266729-28-5

• 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: 4'-hydroxy-3,6,7,8-tetramethoxy-flavone
• 英文别名: 5-deoxycalycopterin；2-(4-Hydroxyphenyl)-3,6,7,8-tetramethoxychromen-4-one
• CAS: 1266729-28-5
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: QXXBYCPTQMTQMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 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：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4'-hydroxy-3,6,7,8-tetramethoxy-flavone 在 硝酸 、 potassium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3'-nitro-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：

  4'-benzyloxy-5-hydroxy-3,6,7,8-tetramethoxy-flavone 在 10% palladium on activated charcoal 、 甲酸铵 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.25h， 生成 4'-hydroxy-3,6,7,8-tetramethoxy-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

文献信息

• [EN] FLAVONES AND COUMARINS AS AGENTS FOR THE TREATMENT OF ATHEROSCLEROSIS<br/>[FR] FLAVONES ET COUMARINES UTILISEES EN TANT QU'AGENTS DANS LE TRAITEMENT DE L'ATHEROSCLEROSE
  申请人：——

  公开号：WO1996031206A2

  公开（公告）日：1996-10-10

  [EN] Flavones and coumarins or a pharmaceutically acceptable salt thereof are inhibitors of VCAM-1 and ICAM-1 and are thus useful in the treatment of atherosclerosis, restenosis, and immune disorders such as arthritis and transplant rejection.
  [FR] Les flavones et les coumarines ou leurs sels pharmaceutiquement acceptables sont des inhibiteurs de VCAM-1 et ICAM-1 et sont donc utiles dans le traitement de l'athérosclérose, de la resténose et de troubles immunitaires tels que l'arthrite et le rejet des transplantations.
• Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.
  作者：Guy Lewin、Narayan Bhat Shridhar、Geneviève Aubert、Sylviane Thoret、Joëlle Dubois、Thierry Cresteil

  DOI：10.1016/j.bmc.2010.11.035

  日期：2011.1

  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.