methyl N-(diphenylmethylene)-5-aminolevulinate | 1448609-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl N-(diphenylmethylene)-5-aminolevulinate
• 英文别名: Methyl 5-(benzhydrylideneamino)-4-oxopentanoate；methyl 5-(benzhydrylideneamino)-4-oxopentanoate
• CAS: 1448609-89-9
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: IXFSSPYJQZOJJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-(diphenylmethylene)-5-aminolevulinate 在 盐酸 、 四丁基氟化铵 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 19.0h， 生成 5-methyl-5-aminolevulinic acid
  参考文献：
  名称：

  Synthesis and in vitro cellular uptake of 11C-labeled 5-aminolevulinic acid derivative to estimate the induced cellular accumulation of protoporphyrin IX

  摘要：

  Protoporphyrin IX (PplX) accumulation induced by exogenous 5-aminolevulinic acid (ALA) in tumors affects the therapeutic efficacy of ALA-based photodynamic and sonodynamic therapies. To develop a new imaging probe to estimate the ALA-induced PpIX accumulation, C-11-labeled ALA analog (4), an ALA-dehydratase inhibitor, was radiosynthesized via C-11-methylation of a Schiff-base-activated precursor in the presence of tetrabutylammonium fluoride, followed by the hydrolysis of ester and imine groups. The cellular uptake of 4 linearly increased with time and was inhibited by ALA and other transporter competitors. Monitoring analog 4 with positron emission tomography might be useful to estimate the ALA-induced PpIX accumulation in tumors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.025
• 作为产物：
  描述：

  二苯甲酮亚胺 、 5-氨基酮戊酸甲酯盐酸盐 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 二苯甲酮 、 methyl N-(diphenylmethylene)-5-aminolevulinate
  参考文献：
  名称：

  Synthesis and in vitro cellular uptake of 11C-labeled 5-aminolevulinic acid derivative to estimate the induced cellular accumulation of protoporphyrin IX

  摘要：

  Protoporphyrin IX (PplX) accumulation induced by exogenous 5-aminolevulinic acid (ALA) in tumors affects the therapeutic efficacy of ALA-based photodynamic and sonodynamic therapies. To develop a new imaging probe to estimate the ALA-induced PpIX accumulation, C-11-labeled ALA analog (4), an ALA-dehydratase inhibitor, was radiosynthesized via C-11-methylation of a Schiff-base-activated precursor in the presence of tetrabutylammonium fluoride, followed by the hydrolysis of ester and imine groups. The cellular uptake of 4 linearly increased with time and was inhibited by ALA and other transporter competitors. Monitoring analog 4 with positron emission tomography might be useful to estimate the ALA-induced PpIX accumulation in tumors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.025