SYNTHESIS OF SOME 3',5'-DIDEOXY-5'-C-PHOSPHONOMETHYL NUCLEOSIDES

被引：6
作者：
IOANNIDIS, P
CLASSON, B
SAMUELSSON, B
KVARNSTROM, I
机构：
[1] UNIV STOCKHOLM,ARRHENIUS LAB,DEPT ORGAN CHEM,S-10691 STOCKHOLM,SWEDEN
[2] LINKOPING UNIV,DEPT CHEM,S-58183 LINKOPING,SWEDEN
[3] AB HASSLE,DEPT ORGAN CHEM,S-43183 MOLNDAL,SWEDEN
来源：
ACTA CHEMICA SCANDINAVICA | 1991年 / 45卷 / 07期
关键词：
D O I：
10.3891/acta.chem.scand.45-0746
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：
Ammonium [1-(3',5',6'-trideoxy-beta-D-erythro-hexofuranosyl)thymine]-6'-phosphonate (1), ammonium 3',5'-dideoxycytidine-5'-C-methylphosphonate (2) and 3',5'-dideoxyadenosine-5'-C-methyl phosphonic acid (3) have been synthesized and tested for anti-HIV activity. The key steps involved an Arbuzov reaction between triethyl phosphite and 3,5,6-trideoxy-6-iodo-1,2-O-isopropylidene-alpha-D-erythro-hexofuranose (7), followed by condensation with the appropriate nucleoside bases. The substances 1, 2 and 3 have been tested in vitro against HIV.
引用
收藏
页码：746 / 750
页数：5
相关论文
共 50 条
  • [41] SYNTHESIS OF 2',3'-DIDEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES AS POTENTIAL INHIBITORS OF HIV
    SVANSSON, L
    KVARNSTROM, I
    CLASSON, B
    SAMUELSSON, B
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) : 2993 - 2997
  • [42] Asymmetric synthesis of 2′,3′-dideoxy-3′-fluoroapiofuranosyl nucleosides
    Jeong, BS
    Lee, JW
    Son, HJ
    Kim, BY
    Ahn, SK
    TETRAHEDRON-ASYMMETRY, 2005, 16 (23) : 3795 - 3801
  • [43] Synthesis of 2',3'-dideoxy-2'-hydroxymethyl nucleosides
    Noe, CR
    Buchstaller, HP
    Haberhauer, G
    Holzner, A
    MONATSHEFTE FUR CHEMIE, 1997, 128 (05): : 509 - 527
  • [44] SYNTHESIS OF 5'-AMINO-2',5'-DIDEOXY AND 5'-AZIDO-2',5'-DIDEOXY NUCLEOSIDES FROM THIENO[2,3-D]PYRIMIDINE-2,4(1H,3H)-DIONE
    ELBARBARY, AA
    ELBROLLOSY, NR
    PEDERSEN, EB
    NIELSEN, C
    MONATSHEFTE FUR CHEMIE, 1995, 126 (05): : 593 - 600
  • [45] SYNTHESIS AND EVALUATION OF 3'-ALKYL-2',3'-DIDEOXY NUCLEOSIDES
    AGYEIAYE, K
    BAKER, DC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 25 - CARB
  • [46] Synthesis and HIV inhibition activity of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides
    LeeRuff, E
    Ostrowski, M
    Ladha, A
    Stynes, DV
    Vernik, I
    Jiang, JL
    Wan, WQ
    Ding, SF
    Joshi, S
    JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) : 5276 - 5280
  • [47] Synthesis of 2',3'-dideoxy-D-C-nucleosides from gamma-lactone.
    Xiang, YJ
    Du, JF
    Chu, CK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 47 - CARB
  • [48] Stereoselective synthesis of 5′-C-methyl pyrimidine nucleosides
    Kel'in, Alexander
    Zlatev, Ivan
    Matsuda, Shigeo
    Jayaraman, Muthusamy
    Rajeev, Kallanthottathil
    Manoharan, Muthiah
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [49] HALO SUGAR NUCLEOSIDES .4. SYNTHESIS OF SOME 4',5'-UNSATURATED PYRIMIDINE NUCLEOSIDES
    VERHEYDEN, JP
    MOFFATT, JG
    JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (24) : 3573 - 3579
  • [50] SYNTHESIS AND CHEMISTRY OF SOME PYRIDAZINE NUCLEOSIDES RELATED TO CERTAIN 5-SUBSTITUTED PYRIMIDINE NUCLEOSIDES
    KATZ, DJ
    WISE, DS
    TOWNSEND, LB
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (02) : 369 - 379
12345