SYNTHESIS OF (Z)-N9-(4-HYDROXY-1-BUTEN-1-YL)ADENINE AND (E)-N9-(4-HYDROXY-1-BUTEN-1-YL)ADENINE - NEW UNSATURATED ANALOGS OF ADENOSINE

被引：14

作者：

PHADTARE, S

ZEMLICKA, J

机构：

[1] MICHIGAN CANC FDN, DEPT CHEM, DETROIT, MI 48201 USA

[2] WAYNE STATE UNIV, SCH MED, DEPT INTERNAL MED, DETROIT, MI 48201 USA

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)94329-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title 1-butenols 5b and 6b were obtained by isomerization of 2-butenols 2b and 3b catalyzed by potassium tert-butoxide ( tBuOK) in dimethylformamide ( DMF). Reaction of Z-olefin 2b was highly stereoselective to give E-isomer 5b whereas E-olefin 3b afforded predominantly Z-isomer 6b. Compounds 5b and 6b are substrates for adenosine deaminase, 6b being substantially less active than 5b. © 1990.

引用

收藏

页码：43 / 46

页数：4

相关论文

共 13 条

[1] SYNTHESIS AND ANTIHERPETIC ACTIVITY OF (+/-)-9-[[(Z)-2-(HYDROXYMETHYL)CYCLOPROPYL]METHYL]GUANINE AND RELATED-COMPOUNDS [J].

ASHTON, WT ;

MEURER, LC ;

CANTONE, CL ;

FIELD, AK ;

HANNAH, J ;

KARKAS, JD ;

LIOU, R ;

PATEL, GF ;

PERRY, HC ;

WAGNER, AF ;

WALTON, E ;

TOLMAN, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2304-2315

[2]

BIRNBAUM GI, 1987, TOPICS NUCLEIC ACI 3, P50

[3] POTENTIAL INHIBITORS OF S-ADENOSYLMETHIONINE-DEPENDENT METHYLTRANSFERASES .11. MOLECULAR DISSECTIONS OF NEPLANOCIN-A AS POTENTIAL INHIBITORS OF S-ADENOSYLHOMOCYSTEINE HYDROLASE [J].

BORCHERDING, DR ;

NARAYANAN, S ;

HASOBE, M ;

MCKEE, JG ;

KELLER, BT ;

BORCHARDT, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) :1729-1738

[4] ADENALLENE AND CYTALLENE - ACYCLIC NUCLEOSIDE ANALOGS THAT INHIBIT REPLICATION AND CYTOPATHIC EFFECT OF HUMAN IMMUNODEFICIENCY VIRUS INVITRO [J].

HAYASHI, S ;

PHADTARE, S ;

ZEMLICKA, J ;

MATSUKURA, M ;

MITSUYA, H ;

BRODER, S .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (16) :6127-6131

[5]

HAYASHI S, UNPUB

[6] SYNTHESIS AND BIOLOGICAL EVALUATION OF ACYCLIC NEPLANOCIN ANALOGS [J].

HUA, M ;

KORKOWSKI, PM ;

VINCE, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (01) :198-200

[7] MODE OF ACTION, TOXICITY, PHARMACOKINETICS, AND EFFICACY OF SOME NEW ANTIHERPES-VIRUS GUANOSINE ANALOGS RELATED TO BUCICLOVIR [J].

LARSSON, A ;

STENBERG, K ;

ERICSON, AC ;

HAGLUND, U ;

YISAK, WA ;

JOHANSSON, NG ;

OBERG, B ;

DATEMA, R .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1986, 30 (04) :598-605

[8] SYNTHESIS OF N1-(4-HYDROXY-1,2-BUTADIEN-1-YL)THYMINE, AN ANALOG OF 3'-DEOXYTHYMIDINE [J].

PHADTARE, S ;

ZEMLICKA, J .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3675-3679

[9] NUCLEIC-ACID DERIVED ALLENOLS - UNUSUAL ANALOGS OF NUCLEOSIDES WITH ANTIRETROVIRAL ACTIVITY [J].

PHADTARE, S ;

ZEMLICKA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5925-5931

[10] UNSATURATED NUCLEOSIDE ANALOGS - SYNTHESIS AND ANTITUMOR-ACTIVITY [J].

PHADTARE, S ;

KESSEL, D ;

ZEMLICKA, J .

NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (5-6) :907-910