SYNTHESIS AND ANTI-HIV ACTIVITY OF 3'-O-FORMYL DERIVATIVES OF THYMIDINE AND 2'-DEOXYURIDINE

被引：3

作者：

KUMAR, R ^{[1
]}

KNAUS, EE ^{[1
]}

WIEBE, LI ^{[1
]}

机构：

[1] UNIV ALBERTA,FAC PHARM & PHARMACEUT SCI,EDMONTON T6G 2N8,ALBERTA,CANADA

来源：

NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 06期

基金：

英国医学研究理事会;

关键词：

D O I：

10.1080/07328319208018337

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：

Reaction of the 5'-O-t-butyldimethylsilyl derivatives of thymidine and 2'-deoxyuridine with the Vilsmeier reagent (POCl3/DMF), and removal of the t-butyldimethylsilyl protecting group, afforded 3'-O-formylthymidine (5) and 3'-O-formyl-2'-deoxyuridine (6), respectively. In vitro evaluation, determined as the ability of the test compound to inhibit HIV induced cytopathogenicity in CEM cells, indicated that 5 was moderately active, whereas 6 was inactive.

引用

页码：1219 / 1228

页数：10

共 17 条

[1] STRUCTURE AND CONFORMATION OF 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT), AN INHIBITOR OF THE HIV (AIDS) VIRUS
BIRNBAUM, GI
GIZIEWICZ, J
GABE, EJ
LIN, TS
PRUSOFF, WH
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09): : 2135 - 2139
[2] CAMERMAN A, 1987, P NATL ACAD SCI USA, V84, P8329
[3] STRUCTURE OF THE ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS AGENT 3'-FLUORO-3'-DEOXYTHYMIDINE AND ELECTRONIC CHARGE CALCULATIONS FOR 3'-DEOXYTHYMIDINES
CAMERMAN, N
MASTROPAOLO, D
CAMERMAN, A
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (09) : 3534 - 3537
[4] MOLECULAR-STRUCTURE OF A DEOXYRIBOSE-DINUCLEOTIDE, SODIUM THYMIDYLYL-(5'-]3')-THYMIDYLATE-(5') HYDRATE (PTPT), AND A POSSIBLE STRUCTURAL MODEL FOR POLYTHYMIDYLATE
CAMERMAN, N
FAWCETT, JK
CAMERMAN, A
[J]. JOURNAL OF MOLECULAR BIOLOGY, 1976, 107 (04) : 601 - 621
[5] FLANDOR J, 1990, TETRAHEDRON LETT, V31, P597
[6] SYNTHESIS, ANTIRETROVIRUS EFFECTS, AND PHOSPHORYLATION KINETICS OF 3'-ISOCYANO-3'-DEOXYTHYMIDINE AND 3'-ISOCYANO-2',3'-DIDEOXYURIDINE
HIEBL, J
ZBIRAL, E
BALZARINI, J
DECLERCQ, E
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) : 845 - 848
[7] HIROTA K, 1984, CHEM PHARM BULL, V32, P2591
[8] HIROTA K, 1983, SYNTHESIS-STUTTGART, P121
[9] FLUORINATED PYRIMIDINES .32. SYNTHESES OF 2',3'-DEHYDRO-5-TRIFLUOROMETHYL-2'-DEOXYURIDINE AND 5-TRIFLUOROMETHYLURIDINE
KHWAJA, TA
HEIDELBERGER, C
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1969, 12 (03) : 543 - +
[10] NUCLEOSIDES AND NUCLEOTIDES .92. SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF 3'-DEOXY-3'-ISOCYANO-THYMIDINES, 3'-DEOXY-3'-ISOTHIOCYANO-THYMIDINES, AND 3'-DEOXY-3'-ISOSELENOCYANO-THYMIDINES
MATSUDA, A
SATOH, M
UEDA, T
MACHIDA, H
SASAKI, T
[J]. NUCLEOSIDES & NUCLEOTIDES, 1990, 9 (04): : 587 - 597

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