SYNTHESIS AND BIOLOGICAL EVALUATION OF 4-CARBAMOYL-2-BETA-D-RIBOFURANOSYL-PYRIDINE

被引：14

作者：

JOOS, PE ^{[1
]}

ESMANS, EL ^{[1
]}

DOMMISSE, RA ^{[1
]}

VANDONGEN, W ^{[1
]}

LEPOIVRE, JA ^{[1
]}

ALDERWEIRELDT, FC ^{[1
]}

BALZARINI, J ^{[1
]}

DECLERCQ, E ^{[1
]}

机构：

[1] CATHOLIC UNIV LEUVEN,ZEGA INST MED RES,B-3000 LOUVAIN,BELGIUM

来源：

NUCLEOSIDES & NUCLEOTIDES | 1991年 / 10卷 / 04期

关键词：

D O I：

10.1080/07328319108046668

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：

D-Allo/D-altro 2-(2,4:3,5-di-O-benzylidenepentitol-1-yl)-4-(4,4-dimethyloxazolin-2-yl)pyridine was synthesized from 2-lithio-4-(4,4-dimethyloxazolin-2-yl)pyridine and 2,4:3,5-di-O-benzylidenealdehydo-D-ribose. After mesylation and subsequent treatment of the adduct with CF3COOH/H2O and then ammonia, 4-carbamoyl-2-D-ribofuranosylpyridine was formed. The alpha- and beta-anomers were separated by semipreparative hplc on a LICHROSORB 10 DIOL column. The beta-anomer had no antiviral activity, but it had modest cytostatic activity against tumor cells.

引用

页码：883 / 894

页数：12

共 12 条

[1] SYNTHESIS AND BIOLOGICAL EVALUATION OF A SERIES OF SUBSTITUTED-2-PYRIDINE-C-NUCLEOSIDES .2. [J].

BELMANS, M ;

VRIJENS, I ;

ESMANS, E ;

DOMMISSE, R ;

LEPOIVRE, J ;

ALDERWEIRELDT, F ;

TOWNSEND, L ;

WOTRING, L ;

BALZARINI, J ;

DECLERCQ, E .

NUCLEOSIDES & NUCLEOTIDES, 1986, 5 (04) :441-455

[2] SYNTHESIS AND BIOLOGICAL EVALUATION OF A SERIES OF SUBSTITUTED 2-PYRIDINE C-NUCLEOSIDES .1. COUPLING REACTION OF ORGANO-METALLIC PYRIDINE COMPOUNDS WITH 2,4-3,5-DI-O-BENZYLIDENE-ALDEHYDO-D-RIBOSE [J].

BELMANS, M ;

ESMANS, E ;

DOMMISSE, R ;

LEPOIVRE, J ;

ALDERWEIRELDT, F ;

BALZARINI, J ;

DECLERCQ, E .

NUCLEOSIDES & NUCLEOTIDES, 1985, 4 (04) :523-538

[3] A study of the preparation of alpha-pyridyl halides from alpha-aminopyridine by the diazo reaction [J].

Craig, LC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :231-232

[4] COMPARATIVE EFFICACY OF ANTIHERPES DRUGS AGAINST DIFFERENT STRAINS OF HERPES-SIMPLEX VIRUS [J].

DECLERCQ, E ;

DESCAMPS, J ;

VERHELST, G ;

WALKER, RT ;

JONES, AS ;

TORRENCE, PF ;

SHUGAR, D .

JOURNAL OF INFECTIOUS DISEASES, 1980, 141 (05) :563-574

[5] ANTIVIRAL AND ANTIMETABOLIC ACTIVITIES OF NEPLANOCINS [J].

DECLERCQ, E .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1985, 28 (01) :84-89

[6]

DECLERCQ E, 1981, MOL PHARMACOL, V19, P321

[7] NUCLEOSIDES .141. SYNTHESIS OF 5-BETA-D-RIBOFURANOSYLNICOTINAMIDE AND ITS N-METHYL DERIVATIVE - THE ISOSTERIC AND ISOELECTRONIC ANALOGS OF NICOTINAMIDE NUCLEOSIDE [J].

KABAT, MM ;

PANKIEWICZ, KW ;

WATANABE, KA .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (05) :924-927

[8] NUCLEOSIDES .148. SYNTHESIS OF 6-(BETA-D-RIBOFURANOSYL)PICOLINAMIDE - A NOVEL C-NUCLEOSIDE FROM D-RIBONOLACTONE [J].

KABAT, MM ;

PANKIEWICZ, KW ;

SOCHACKA, E ;

WATANABE, KA .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1988, 36 (02) :634-640

[9] SENSITIVE AND RAPID ASSAY ON MT-4 CELLS FOR DETECTION OF ANTIVIRAL COMPOUNDS AGAINST THE AIDS VIRUS [J].

PAUWELS, R ;

DECLERCQ, E ;

DESMYTER, J ;

BALZARINI, J ;

GOUBAU, P ;

HERDEWIJN, P ;

VANDERHAEGHE, H ;

VANDEPUTTE, M .

JOURNAL OF VIROLOGICAL METHODS, 1987, 16 (03) :171-185

[10]

VRIJENS Y, 1986, 4TH P FECHEM C HET B, P207

← 1 2 →