A PHOSPHORAMIDITE-BASED SYNTHESIS OF PHOSPHORAMIDATE AMINO-ACID DIESTERS OF ANTIVIRAL NUCLEOSIDES

被引：42

作者：

ABRAHAM, TW ^{[1
]}

WAGNER, CR ^{[1
]}

机构：

[1] UNIV MINNESOTA,COLL PHARM,DEPT MED CHEM,MINNEAPOLIS,MN 55455

来源：

NUCLEOSIDES & NUCLEOTIDES | 1994年 / 13卷 / 09期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1080/15257779408010671

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A general synthetic procedure is presented for the preparation of 5'-amino acid phosphoramidates of zidovudine (AZT), 3'-deoxy-2',3'-didehydrothymidine (D4T), and 3'-fluoro-3'-deoxythymidine (FLT) from their corresponding phosphoramidites. These water soluble amino acid phosphoramidates are more non-polar than the parent nucleoside and exhibit high stability in aqueous media.

引用

页码：1891 / 1903

页数：13

共 15 条

[1] BIOLOGICALLY REVERSIBLE PHOSPHATE-PROTECTIVE GROUPS [J].

FARQUHAR, D ;

SRIVASTVA, DN ;

KUTTESCH, NJ ;

SAUNDERS, PP .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1983, 72 (03) :324-325

[2]

HAO Z, 1988, MOL PHARMACOL, V34, P431

[3] LIPOPHILIC GLYCOSYL PHOSPHOTRIESTER DERIVATIVES OF AZT - SYNTHESIS, NMR TRANSMEMBRANE TRANSPORT STUDY, AND ANTIVIRAL ACTIVITY [J].

HENIN, Y ;

GOUYETTE, C ;

SCHWARTZ, O ;

DEBOUZY, JC ;

NEUMANN, JM ;

HUYNHDINH, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1830-1837

[4]

HOSTETLER KY, 1990, J BIOL CHEM, V265, P6112

[5] ARYL PHOSPHATE DERIVATIVES OF AZT RETAIN ACTIVITY AGAINST HIV-1 IN CELL-LINES WHICH ARE RESISTANT TO THE ACTION OF AZT [J].

MCGUIGAN, C ;

PATHIRANA, RN ;

MAHMOOD, N ;

DEVINE, KG ;

HAY, AJ .

ANTIVIRAL RESEARCH, 1992, 17 (04) :311-321

[6] PHOSPHORAMIDATE DERIVATIVES OF AZT AS INHIBITORS OF HIV - STUDIES ON THE CARBOXYL TERMINUS [J].

MCGUIGAN, C ;

PATHIRANA, RN ;

CHOI, SSM ;

KINCHINGTON, D ;

OCONNOR, TJ .

ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1993, 4 (02) :97-101

[7] ATTEMPTS TO INTRODUCE CHEMOTHERAPEUTIC NUCLEOTIDES INTO CELLS - STUDIES ON THE ANTI-HIV AGENT FDT [J].

MCGUIGAN, C ;

JONES, BCNM ;

DEVINE, KG ;

NICHOLLS, SR ;

OCONNOR, TJ ;

KINCHINGTON, D .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (12) :729-732

[8] PHOSPHATE DERIVATIVES OF D4T AS INHIBITORS OF HIV [J].

MCGUIGAN, C ;

SHEEKA, HM ;

MAHMOOD, N ;

HAY, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (06) :1203-1206

[9] O-ALKYL-5',5'-DINUCLEOSIDE PHOSPHATES AS PRODRUGS OF 3'-AZIDOTHYMIDINE AND CORDYCEPIN [J].

MEIER, C ;

NEUMANN, JM ;

ANDRE, F ;

HENIN, Y ;

HUYNHDINH, T .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7300-7308

[10] DIRECTED ARBUZOV-TYPE REACTIONS OF 2-CYANO-1,1-DIMETHYLETHYL DEOXYNUCLEOSIDE PHOSPHITES [J].

NIELSEN, J ;

CARUTHERS, MH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6275-6276

← 1 2 →