Synthesis and biological evaluation of the L-enantiomer of 2'-deoxy-5-ethyl-4'-thiouridine

被引：25

作者：

Selwood, DL ^{[1
]}

Carter, K ^{[1
]}

Young, RJ ^{[1
]}

Jandu, KS ^{[1
]}

机构：

[1] WELLCOME RES LABS, DEPT MED CHEM, BECKENHAM BR3 3BS, KENT, ENGLAND

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 08期

关键词：

D O I：

10.1016/0960-894X(96)00161-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Racemic 2'-deoxy-5-ethyl-4'-thiouridine was synthesised utilising the stereoselective iodolactonisation of 3-(tert-butyldimethyIsilyl)oxy-N,N-dimethyl-4-pentenamide as the key transformation. The stereo-isomeric mixture of nucleosides was resolved using HPLC on a Chiralcel OJ column. The beta-D enantiomer showed potent activity against human herpesviruses while the beta-L was inactive. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：991 / 994

页数：4

共 15 条

[1] STEREOSELECTIVE IODOLACTONIZATION OF ACYCLIC UNSATURATED 3-HYDROXYACIDS [J].

CHAMBERLIN, AR ;

DEZUBE, M ;

DUSSAULT, P .

TETRAHEDRON LETTERS, 1981, 22 (46) :4611-4614

[2] THE SEPARATED ENANTIOMERS OF 2'-DEOXY-3'-THIACYTIDINE (BCH-189) BOTH INHIBIT HUMAN-IMMUNODEFICIENCY-VIRUS REPLICATION INVITRO [J].

COATES, JAV ;

CAMMACK, N ;

JENKINSON, HJ ;

MUTTON, IM ;

PEARSON, BA ;

STORER, R ;

CAMERON, JM ;

PENN, CR .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (01) :202-205

[3] THE ANTI-HEPATITIS-B VIRUS ACTIVITIES, CYTOTOXICITIES, AND ANABOLIC PROFILES OF THE (-) AND (+) ENANTIOMERS OF CIS-5-FLUORO-1-[2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]CYTOSINE [J].

FURMAN, PA ;

DAVIS, M ;

LIOTTA, DC ;

PAFF, M ;

FRICK, LW ;

NELSON, DJ ;

DORNSIFE, RE ;

WURSTER, JA ;

WILSON, LJ ;

FYFE, JA ;

TUTTLE, JV ;

MILLER, WH ;

CONDREAY, L ;

AVERETT, DR ;

SCHINAZI, RF ;

PAINTER, GR .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (12) :2686-2692

[4]

GROVE KL, 1995, CANCER RES, V55, P3008

[5] EPOXIDE-EPISULPHIDE TRANSFORMATION [J].

HALL, LD ;

HOUGH, L ;

PRITCHARD, RA .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (APR) :1537-&

[6] 4'-THIONUCLEOSIDES VIA IN-SITU PYRANOSE-FURANOSE REARRANGEMENTS - A SHORT SYNTHESIS OF THE ANTIHERPES AGENT 2'-DEOXY-5-ETHYL-4'-THIOURIDINE VIA DIRECT COUPLING OF A SILYLATED PYRIMIDINE BASE WITH A 4-THIOPYRANOSE SUGAR [J].

JANDU, KS ;

SELWOOD, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :5170-5173

[7] A NEW METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF NUCLEOSIDES FROM ACYCLIC EPOXY ALDEHYDES [J].

MIWA, T ;

NARASAKA, K ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1984, (07) :1093-1096

[8] Synthesis and anti-herpes virus activity of 2'-deoxy-4'-thiopyrimidine nucleosides [J].

Rahim, SG ;

Trivedi, N ;

BogunovicBatchelor, MV ;

Hardy, GW ;

Mills, G ;

Selway, JWT ;

Snowden, W ;

Littler, E ;

Coe, PL ;

Basnak, I ;

Whale, RF ;

Walker, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (03) :789-795

[9] DERIVATIVES OF ALPHA-D-GLUCOTHIOPYRANOSE [J].

ROWELL, RM ;

WHISTLER, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (05) :1514-&

[10] PURE NUCLEOSIDE ENANTIOMERS OF BETA-2',3'-DIDEOXYCYTIDINE ANALOGS ARE SELECTIVE INHIBITORS OF HEPATITIS-B VIRUS IN-VITRO [J].

SCHINAZI, RF ;

GOSSELIN, G ;

FARAJ, A ;

KORBA, BE ;

LIOTTA, DC ;

CHU, CK ;

MATHE, C ;

IMBACH, JL ;

SOMMADOSSI, JP .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1994, 38 (09) :2172-2174

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