Synthesis of the 5′-phosphonate of 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol [S,S-IsoddA]

被引：8
作者：
Nair, V [1 ]
Sharma, PK
机构：
[1] Univ Georgia, RC Wilson PH, Dept Pharmaceut & Biomed Sci, Athens, GA 30602 USA
[2] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
来源：
ARKIVOC | 2003年
关键词：
synthesis; isonucleoside; phosphonate; anti-HIV;
D O I：
10.3998/ark.5550190.0004.f02
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4(S)-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2(S)-ylmethyl phosphonic acid, a 5'-C-phosphonate analog of the potent anti-HIV compound S,S-IsoddA, was synthesized in order to bypass the critical initial intracellular phosphorylation. Key phases in this multistep synthesis were the Arbuzov reaction of the 5-iodofuranose with triethylphosphite and the Mitsunobu/coupling reaction of the phosphonate with adenine. The structure of the final product was confirmed by HRMS and multinuclear NMR data.
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收藏
页码：10 / 14
页数：5
相关论文
共 19 条
  • [1] INTRACELLULAR METABOLISM AND MECHANISM OF ANTIRETROVIRUS ACTION OF 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE, A POTENT ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS COMPOUND
    BALZARINI, J
    ZHANG, H
    HERDEWIJN, P
    JOHNS, DG
    DECLERCQ, E
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (04) : 1499 - 1503
  • [2] DIFFERENTIAL ANTIHERPESVIRUS AND ANTIRETROVIRUS EFFECTS OF THE (S) AND (R) ENANTIOMERS OF ACYCLIC NUCLEOSIDE PHOSPHONATES - POTENT AND SELECTIVE INVITRO AND INVIVO ANTIRETROVIRUS ACTIVITIES OF (R)-9-(2-PHOSPHONOMETHOXYPROPYL)-2,6-DIAMINOPURINE
    BALZARINI, J
    HOLY, A
    JINDRICH, J
    NAESENS, L
    SNOECK, R
    SCHOLS, D
    DECLERCQ, E
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1993, 37 (02) : 332 - 338
  • [3] 9-[(2RS)-3-FLUORO-2-PHOSPHONYLMETHOXYPROPYL] DERIVATIVES OF PURINES - A CLASS OF HIGHLY SELECTIVE ANTIRETROVIRAL AGENTS INVITRO AND INVIVO
    BALZARINI, J
    HOLY, A
    JINDRICH, J
    DVORAKOVA, H
    HAO, Z
    SNOECK, R
    HERDEWIJN, P
    JOHNS, DG
    DECLERCQ, E
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (11) : 4961 - 4965
  • [4] BLACKBURN GM, 1981, CHEM IND-LONDON, P134
  • [5] NOVEL ISOMERIC DIDEOXYNUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS
    BOLON, PJ
    SELLS, TB
    NUESCA, ZM
    PURDY, DF
    NAIR, V
    [J]. TETRAHEDRON, 1994, 50 (26) : 7747 - 7764
  • [6] INITIAL STUDIES ON THE CELLULAR PHARMACOLOGY OF 2',3'-DIDEOXYADENOSINE, AN INHIBITOR OF HTLV-III INFECTIVITY
    COONEY, DA
    AHLUWALIA, G
    MITSUYA, H
    FRIDLAND, A
    JOHNSON, M
    HAO, Z
    DALAL, M
    BALZARINI, J
    BRODER, S
    JOHNS, DG
    [J]. BIOCHEMICAL PHARMACOLOGY, 1987, 36 (11) : 1765 - 1768
  • [7] Strategies in the design of antiviral drugs
    De Clercq, E
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (01) : 13 - 25
  • [8] In search of a selective antiviral chemotherapy
    DeClercq, E
    [J]. CLINICAL MICROBIOLOGY REVIEWS, 1997, 10 (04) : 674 - +
  • [9] A NOVEL SELECTIVE BROAD-SPECTRUM ANTI-DNA VIRUS AGENT
    DECLERCQ, E
    HOLY, A
    ROSENBERG, I
    SAKUMA, T
    BALZARINI, J
    MAUDGAL, PC
    [J]. NATURE, 1986, 323 (6087) : 464 - 467
  • [10] PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES
    ENGEL, R
    [J]. CHEMICAL REVIEWS, 1977, 77 (03) : 349 - 367
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