1-O-octadecyl-2-(4-(4-(bis-(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phospho-(S)-2,3-di-O-tert-butyldimethylsilylglycerol | 1159279-54-5

• 分子结构分类: 有机化合物
• 英文名称: 1-O-octadecyl-2-(4-(4-(bis-(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phospho-(S)-2,3-di-O-tert-butyldimethylsilylglycerol
• 英文别名: [(2R)-1-[[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propoxy]-hydroxyphosphoryl]oxy-3-octadecoxypropan-2-yl] 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate
• CAS: 1159279-54-5
• 化学式: C₅₀H₉₆Cl₂NO₉PSi₂
• 分子量: 1013.36
• InChiKey: YAUHEJVFZMSFCY-NZCKGYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.03
• 重原子数：
  65
• 可旋转键数：
  43
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-O-octadecyl-2-(4-(4-(bis-(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phospho-(S)-2,3-di-O-tert-butyldimethylsilylglycerol 在 氢氟酸 、 水 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以32%的产率得到1-O-octadecyl-2-(4-(4-(bis(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phospho-(S)-glycerol
  参考文献：
  名称：

  Synthesis and Biophysical Characterization of Chlorambucil Anticancer Ether Lipid Prodrugs

  摘要：

  The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol headgroups. All four prodrugs have the ability to form unilamellar liposomes (86-125 nm) and are hydrolyzed by phospholipase A(2), resulting in chlorambucil release. Liposomal formulations of prodrug lipids displayed cytotoxicity toward HT-29, MT-3, and ES-2 cancer cell lines in the presence of phospholipase A(2), with IC50 values in the 8-36 mu M range.

  DOI：

  10.1021/jm900091h
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以57%的产率得到1-O-octadecyl-2-(4-(4-(bis-(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phospho-(S)-2,3-di-O-tert-butyldimethylsilylglycerol
  参考文献：
  名称：

  Synthesis and Biophysical Characterization of Chlorambucil Anticancer Ether Lipid Prodrugs

  摘要：

  The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol headgroups. All four prodrugs have the ability to form unilamellar liposomes (86-125 nm) and are hydrolyzed by phospholipase A(2), resulting in chlorambucil release. Liposomal formulations of prodrug lipids displayed cytotoxicity toward HT-29, MT-3, and ES-2 cancer cell lines in the presence of phospholipase A(2), with IC50 values in the 8-36 mu M range.

  DOI：

  10.1021/jm900091h