【药物名称】Azidothymidine phosphonate, Nicavir, Phosphazid, phAZT
化学结构式(Chemical Structure):
参考文献No.48063
标题:5'-Hydrogenphosphonates and 5'-methylphosphonates of sugar modified nucleosides, compsns. and uses thereof
作者:Krayevsky, A.A.; Tarussova, N.B.; Watanabe, K.A.; Matulic-Adamic, J. (Sloan-Kettering Institute)
来源:WO 9119727
合成路线图解说明:

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.

参考文献No.233390
标题:Nucleoside 5'-phosphonates: Synthesis, anti-HIV activities and reactions with DNA polymerases
作者:Dyatkina, N.; et al.
来源:Antivir Res 1993,20(Suppl. 1),Abst 24
合成路线图解说明:

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.

参考文献No.321295
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
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.
来源:Antivir Chem Chemother 1995,6(4),230
合成路线图解说明:

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.

合成路线图解说明:

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.

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