CYCLOHEXENYL NUCLEOSIDES AND RELATED-COMPOUNDS

被引：28

作者：

ARANGO, JH ^{[1
]}

GEER, A ^{[1
]}

RODRIGUEZ, J ^{[1
]}

YOUNG, PE ^{[1
]}

SCHEINER, P ^{[1
]}

机构：

[1] CUNY YORK COLL,JAMAICA,NY 11451

来源：

NUCLEOSIDES & NUCLEOTIDES | 1993年 / 12卷 / 07期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1080/07328319308021509

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：

Cis and trans-1-(4-hydroxy-2-cyclohexenyl)- and 1-(2-hydroxy-5-cyclohexenyl)thymines were obtained by stereospecific routes. Oxidation of the 1,4-products afforded 1-(4-oxo-2-cyclohexenyl)thymine, the carbocyclic analog of a reportedly antiviral ketopyranosyl nucleoside. Exclusive 1,6-conjugate addition occurred with heterocyclic bases and methyl 1,3-cyclohexadiene-1-carboxylate. Reduction of the thymine adduct gave 1-(4-hydroxymethyl-3-cyclohexenyl)thymine. Michael-type addition provided a direct route to 3-oxocycloalkyl. nucleosides, and lactone nucleosides resulted from addition of bases to alpha-methylene-gamma-butyrolactone. Anti-HIV screening revealed no activity for the new compounds.

引用

收藏

页码：773 / 784

页数：12

相关论文

共 33 条

[1] STUDIES ON BIOCHEMICAL BASIS FOR ANTIVIRAL ACTIVITIES OF SOME NUCLEOSIDE ANALOGS [J].

BENNETT, LL ;

SHANNON, WM ;

ALLAN, PW ;

ARNETT, G .

ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, 1975, 255 (AUG8) :342-358

[2] SYNTHESIS OF UNSATURATED 4'-AZIDO PYRANOSYL THYMINES AS POTENTIAL ANTIVIRAL AND ANTI-HIV AGENTS [J].

BESSODES, M ;

EGRON, MJ ;

FILIPPI, J ;

ANTONAKIS, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3035-3039

[3]

BUCKVALL JE, 1990, ORG SYN, V69, P38

[4] CARBOVIR - THE (-) ENANTIOMER IS A POTENT AND SELECTIVE ANTIVIRAL AGENT AGAINST HUMAN-IMMUNODEFICIENCY-VIRUS INVITRO [J].

COATES, JAV ;

INGGALL, HJ ;

PEARSON, BA ;

PENN, CR ;

STORER, R ;

WILLIAMSON, C ;

CAMERON, JM .

ANTIVIRAL RESEARCH, 1991, 15 (02) :161-168

[5] PREPARATION OF NUCLEOTIDE MIMICS WITH POTENT INHIBITORY ACTIVITY AGAINST HIV REVERSE-TRANSCRIPTASE [J].

COE, DM ;

ORR, DC ;

ROBERTS, SM ;

STORER, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3378-3379

[6] A SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].

CRANDALL, JK ;

BANKS, DB ;

COLYER, RA ;

WATKINS, RJ ;

ARRINGTO.JP .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) :423-&

[7] SYNTHESE UND REAKTIONEN 1-SUBSTITUIERTER BICYCLO-[2,2,2]-OCTANE - UNTERSUCHUNGEN IN DER BICYCLO-[2,2,2]-OCTAN-REIHE .2. [J].

GROB, CA ;

OHTA, M ;

RENK, E ;

WEISS, A .

HELVETICA CHIMICA ACTA, 1958, 41 (05) :1191-1197

[8] INTERACTIONS OF CYTOSTATIC UNSATURATED KETONUCLEOSIDES WITH SULFHYDRYL CONTAINING CELL CONSTITUENTS [J].

HALMOS, T ;

CARDON, A ;

ANTONAKIS, K .

CHEMICO-BIOLOGICAL INTERACTIONS, 1983, 46 (01) :11-29

[9]

HANSEN P, 1990, LIEBIGS ANN CHEM, P1079

[10] STUDIES ON NEPLANOCIN-A, NEW ANTI-TUMOR ANTIBIOTIC .2. STRUCTURE DETERMINATION [J].

HAYASHI, M ;

YAGINUMA, S ;

YOSHIOKA, H ;

NAKATSU, K .

JOURNAL OF ANTIBIOTICS, 1981, 34 (06) :675-680

← 1 2 3 4 →