DPP-AZT
Chemical Name: 3'-Azido-3'-deoxy-5'-O-[2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]thymidine; 3'-Azido-3'-deoxythymidilic acid mono[2,3-bis(hexadecanoyloxy)propyl] ester
CAS No. 161106-33-8, 128506-56-9 ((R)-isomer), 167354-90-7 ((S)-isomer), 177084-49-0 (Na salt)
项目整合开发状态: Preclinical
项目研究机构: University of Georgia (Originator)
合成路线:The title compound was obtained from 3'-azido-3'-deoxythymidine (I) either by treatment with tri-n-butylammonium phosphite and DCC in pyridine or by treatment with phosphorus trichloride in the presence of imidazole and Et3N in acetonitrile or in the presence of triethyl phosphate,followed by aqueous hydrolysis.
合成路线:3'-azido-3'-deoxythimidine (II) was phosphitylated with phosphorus trichloride in triethyl phosphate to yield the corresponding hydrogen phosphonate (III).Subsequent coupling of (III) with 1,2-dipalmitoylglycerol (IV) by means of pivaloyl chloride in pyridine produced phosphite ester (V),which was finally oxidized to the title phosphate with ethanolic iodine.
📌 参考资料/链接：
参考文献标题:Lymphatic targeting of anti-HIV nucleosides: Distribution of 3'-azido-3'-deoxythymidine (AZT) and 3'-azido-2',3'-dideoxyuridine (AZdU) after administration of dipalmitoylphosphatidyl prodrugs to mice
文献作者:Manouilov,K.K.; Fedorov,I.I.; Boudinot,F.D.; White,C.A.; Kotra,L.P.; Schinazi,R.F.; Hong,C.I.; Chu,C.K.
参考来源:Antivir Chem Chemother 1995,6(4),230
📄 详细内容
合成路线:The synthesis of the title compound has been reported by two procedures.Coupling of dipalmitoylphosphatidic acid (I) to 3'-azido-3'-deoxythimidine (AZT) (II) was carried out using triisopropylbenzenesulfonyl chloride in pyridine to provide the target phosphate diester.
参考文献标题:Phosphatidylazidothymidine and phosphatidyl-ddC: Assessment of uptake in mouse lymphoid tissues and antiviral activities in human immunodeficiency virus-infected cells and in rauscher leukemia virus-infected mice
文献作者:Hostetler,K.Y.; Richman,D.D.; Sridhar,C.N.; Felgner,P.L.; Felgner,J.; Ricci,J.; Gardner,M.F.; Selleseth,D.W.; Ellis,M.N.
参考来源:Antimicrob Agents Chemother 1994,38(12),2792