(E)-5-(3-OXOPROPEN-1-YL)-2'-DEOXYURIDINE AND (E)-5-(3-OXOPROPEN-1-YL)-2',3'-DIDEOXYURIDINE - NEW ANTIVIRAL AGENTS - SYNTHESIS AND BIOLOGICAL-ACTIVITY

被引：7

作者：

CHO, YM

JOHNSON, F

机构：

[1] SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794

[2] SUNY STONY BROOK,DEPT PHARMACOL,STONY BROOK,NY 11794

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 08期

关键词：

D O I：

10.1016/0040-4039(94)88009-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of the 5-(3-oxopropen-1-yl) derivatives of dU (5) and ddU (6) and their biological activity are reported. Good antiviral activity (EC(50), 1.4 mu g/mL) and selectivity (SI > 71.4) is shown by 5 against VZV, whereas in the case of 6 the antiviral activity (EC(50), 2.6 mu g/mL; SI > 38.5) against EBV is greater than that of Acyclovir (EC(50), 9.3 mu g/mL).

引用

收藏

页码：1149 / 1152

页数：4

相关论文

共 14 条

[1] C-5-SUBSTITUTED PYRIMIDINE NUCLEOSIDES .3. REACTION OF ALLYLIC CHLORIDES, ALCOHOLS, AND ACETATES WITH PYRIMIDINE NUCLEOSIDE DERIVED ORGANOPALLADIUM INTERMEDIATES [J].

BERGSTROM, DE ;

RUTH, JL ;

WARWICK, P .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1432-1441

[2] C-5 SUBSTITUTED PYRIMIDINE NUCLEOSIDES .2. SYNTHESIS VIA OLEFIN COUPLING TO ORGANOPALLADIUM INTERMEDIATES DERIVED FROM URIDINE AND 2'-DEOXYURIDINE [J].

BERGSTROM, DE ;

OGAWA, MK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (26) :8106-8112

[3] SYNTHESIS OF C-5 SUBSTITUTED PYRIMIDINE NUCLEOSIDES VIA ORGANO-PALLADIUM INTERMEDIATES [J].

BERGSTROM, DE ;

RUTH, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (06) :1587-1589

[4]

BERGSTROM DE, 1977, J CARB-NUCLEOS-NUCL, V4, P257

[5]

COREY EJ, 1979, TETRAHEDRON LETT, P399

[6]

DECLERCQ E, 1979, P NATL ACAD SCI USA, V76, P2947, DOI 10.1073/pnas.76.6.2947

[7] THE CARBOCYCLIC ANALOG OF 5-(1-PROPENYL)-2'-DEOXYURIDINE - SYNTHESIS AND ANTI-HERPES ACTIVITY [J].

GOODCHILD, J ;

WADSWORTH, HJ ;

SIM, IS .

NUCLEOSIDES & NUCLEOTIDES, 1986, 5 (05) :571-578

[8]

GROLLMAN AP, 1985, CANCER RES, V45, P1127

[9] ELECTRONIC AND STERIC EFFECTS IN OLEFIN ARYLATION AND CARBOALKOXYLATION REACTIONS WITH ORGANOPALLADIUM COMPOUNDS [J].

HECK, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (25) :6896-&

[10] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF A NEW CLASS OF CYTO-TOXIC AGENTS - N-(3-OXOPROP-1-ENYL)-SUBSTITUTED PYRIMIDINES AND PURINES [J].

JOHNSON, F ;

PILLAI, KMR ;

GROLLMAN, AP ;

TSENG, L ;

TAKESHITA, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (08) :954-958