2',3',4',5'-tetracetyl-3-(2-hydroxyethyl)-riboflavin | 929540-63-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2',3',4',5'-tetracetyl-3-(2-hydroxyethyl)-riboflavin
• CAS: 929540-63-6
• 化学式: C₂₇H₃₂N₄O₁₁
• 分子量: 588.571
• InChiKey: DBFXCMWTGHNVMH-ZDXQCDESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  195.21
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2',3',4',5'-tetracetyl-3-(2-hydroxyethyl)-riboflavin 在 吡啶 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 2',3',4',5'-tetracetyl-3-{2-{[1-(4-isobutylphenyl)ethyl]carbonyloxy}ethyl}riboflavin
  参考文献：
  名称：

  Synthesis and biological activities of novel dexibuprofen tetraacetylriboflavin conjugates

  摘要：

  A series of novel dexibuprofen derivatives covalently linked via alkylene spacers of variable length to tetraacetylated riboflavin have been developed. The target compounds became accessible by reaction of the chloromethyl ester of dexibuprofen with tetraacetylriboflavin (compound 7) or by synthesis of the appropriate N3-(omega-iodoalkyl)-2',3',4',5'-tetraacetylriboflavin followed by treatment with dexibuprofen (derivatives 8-11), respectively. Biological screening revealed that the target compounds exhibit antiproliferative effects on MCF-7 breast cancer and HT-29 colon carcinoma cells with IC(50) values in the range of 8-15 VM. Enzymatic studies on human platelets indicated significant COX-1 inhibitory activities of the target compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.087
• 作为产物：
  描述：

  维生素 B2 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 2',3',4',5'-tetracetyl-3-(2-hydroxyethyl)-riboflavin
  参考文献：
  名称：

  Synthesis and biological activities of novel dexibuprofen tetraacetylriboflavin conjugates

  摘要：

  A series of novel dexibuprofen derivatives covalently linked via alkylene spacers of variable length to tetraacetylated riboflavin have been developed. The target compounds became accessible by reaction of the chloromethyl ester of dexibuprofen with tetraacetylriboflavin (compound 7) or by synthesis of the appropriate N3-(omega-iodoalkyl)-2',3',4',5'-tetraacetylriboflavin followed by treatment with dexibuprofen (derivatives 8-11), respectively. Biological screening revealed that the target compounds exhibit antiproliferative effects on MCF-7 breast cancer and HT-29 colon carcinoma cells with IC(50) values in the range of 8-15 VM. Enzymatic studies on human platelets indicated significant COX-1 inhibitory activities of the target compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.087