tetra-O-palmitoyl riboflavin | 752-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: tetra-O-palmitoyl riboflavin
• 英文别名: Riboflavin-tetrapalmitat；O^{2'_,O3'_,O4'_,O5'}-tetrahexadecanoyl-riboflavin；[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-tri(hexadecanoyloxy)pentyl] hexadecanoate
• CAS: 752-75-0
• 化学式: C₈₁H₁₄₀N₄O₁₀
• 分子量: 1330.02
• InChiKey: CBDSOYQURHPMIZ-OLGYWZOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30.1
• 重原子数：
  95
• 可旋转键数：
  69
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  棕榈酰氯 、 维生素 B2 在 4-二甲氨基吡啶 作用下， 反应 12.0h， 以67%的产率得到tetra-O-palmitoyl riboflavin
  参考文献：
  名称：

  Riboflavin derivatives for enhanced photodynamic activity against Leishmania parasites

  摘要：

  Riboflavin derivatives with various substituents (O-acyl, N-methyl, N-alkylcarboxyalkyl or N-alkyl(trialkyl) ammonium) have been prepared and spectroscopically characterized (absorption, emission and fluorescence quantum yields). Their quantum yields of photosensitized singlet molecular oxygen production (Phi(Delta) 0.24-0.58) and octanol/water partition coefficients (P-ow <= 0.01-11) were measured. Preliminary studies indicate that all derivatives display higher phototoxicity against the human protozoan parasite Leishmania than the parent riboflavin, with negligible toxicity in the absence of light. Their photodynamic action shows a higher correlation with Pow than with Phi(Delta), opening up their potential application to cutaneous diseases treatment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.072

文献信息

• Riboflavin derivatives for enhanced photodynamic activity against Leishmania parasites
  作者：Alexandre Vieira Silva、Almudena López-Sánchez、Helena Couto Junqueira、Luis Rivas、Mauricio S. Baptista、Guillermo Orellana

  DOI：10.1016/j.tet.2014.11.072

  日期：2015.1

  Riboflavin derivatives with various substituents (O-acyl, N-methyl, N-alkylcarboxyalkyl or N-alkyl(trialkyl) ammonium) have been prepared and spectroscopically characterized (absorption, emission and fluorescence quantum yields). Their quantum yields of photosensitized singlet molecular oxygen production (Phi(Delta) 0.24-0.58) and octanol/water partition coefficients (P-ow <= 0.01-11) were measured. Preliminary studies indicate that all derivatives display higher phototoxicity against the human protozoan parasite Leishmania than the parent riboflavin, with negligible toxicity in the absence of light. Their photodynamic action shows a higher correlation with Pow than with Phi(Delta), opening up their potential application to cutaneous diseases treatment. (C) 2014 Elsevier Ltd. All rights reserved.