2-[(4-{4-[二(2-氯乙基)氨基]苯基}丁酰基)氧基]-1,3-丙烷二基二十六烷酸酯 | 85763-07-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 2-[(4-{4-[二(2-氯乙基)氨基]苯基}丁酰基)氧基]-1,3-丙烷二基二十六烷酸酯
• 英文名称: 1,3-dipalmitoyl-2-[4-(bis(2-chloroethyl)amino)benzenebutanoyl]glycerol
• 英文别名: 1,3-DP-Chlorambucil；[2-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyloxy]-3-hexadecanoyloxypropyl] hexadecanoate
• CAS: 85763-07-1
• 化学式: C₄₉H₈₅Cl₂NO₆
• 分子量: 855.123
• InChiKey: ONYSZSAXTDHFPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.2
• 重原子数：
  58
• 可旋转键数：
  45
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯丁酸氮芥 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 72.0h， 生成 2-[(4-{4-[二(2-氯乙基)氨基]苯基}丁酰基)氧基]-1,3-丙烷二基二十六烷酸酯
  参考文献：
  名称：

  1,3-Dipalmitoylglycerol ester of chlorambucil as a lymphotropic, orally administrable antineoplastic agent

  摘要：

  A glyceride derivative of chlorambucil (2), 1,3-dipalmitoyl-2-[4-[bis (2-chloroethyl)amino]benzenebutanoyl]glycerol (1), was synthesized and tested as an orally administrable antineoplastic drug endowed with lymphotropic properties. A significantly higher efficacy (increased life span) and a reduced toxicity of 1, relative to 2, were apparent when both compounds given per os were evaluated against P388 leukemia subcutaneously implanted in mice, a situation where the tumor cells disseminate along the lymphatic route. In order to assess the selective absorption of 1 by the intestinal lymphatic system after oral administration, we determined plasma and intestinal lymphatic concentrations and compared them with that obtained with 2. The results clearly demonstrate that the esterification of 2 to a diacylglycerol moiety brings about considerably higher levels in the lymph and reduces plasma levels. Moreover, pharmacokinetic and biological data suggest that 1 is most probably acting by itself rather than as a prodrug of chlorambucil.

  DOI：

  10.1021/jm00362a021

文献信息

• GARZON-ABURBEH, A.;POUPAERT, J. H.;CLAESEN, M.;DUMONT, P.;ATASSI, G., J. MED. CHEM., 1983, 26, N 8, 1200-1203
  作者：GARZON-ABURBEH, A.、POUPAERT, J. H.、CLAESEN, M.、DUMONT, P.、ATASSI, G.

  DOI：——

  日期：——