Geminal hydroxy phosphonate derivatives of nucleosides:: A novel class of nucleoside 5′-monophosphate analogues

被引:23
|
作者
Králíková, S [1 ]
Budesínsky, M [1 ]
Masojídková, M [1 ]
Rosenberg, I [1 ]
机构
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(99)02107-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel type of phosphonate-based, isopolar, nonisosteric 5'-nucleotide analogue, the nucleoside 5'-hydroxy phosphonates, was prepared by Abramov nucleophilic addition of various phosphorous acid esters to nucleoside 5'-aldehydes. The newly formed compounds are distinguished by chirality of the 5'-carbon atom. The configuration of the 5'-epimers was assigned from NMR spectra. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:955 / 958
页数:4
相关论文
共 50 条
  • [1] Symmetrical Diamidates as a Class of Phosphate Prodrugs to Deliver the 5′-Monophosphate Forms of Anticancer Nucleoside Analogues
    Slusarczyk, Magdalena
    Ferrari, Valentina
    Serpi, Michaela
    Goenczy, Blanka
    Balzarini, Jan
    McGuigan, Christopher
    CHEMMEDCHEM, 2018, 13 (21) : 2305 - 2316
  • [2] Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives
    Vertuani, Silvia
    Baldisserotto, Anna
    Varani, Katia
    Borea, Pier Andrea
    Maria Cruz, Bonache De Marcos
    Ferraro, Luca
    Manfredini, Stefano
    Dalpiaz, Alessandro
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 : 202 - 209
  • [3] Synthesis of 5′-amino-5′-phosphonate analogues of pyrimidine nucleoside monophosphates
    Chen, XM
    Wiemer, DF
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16): : 6108 - 6114
  • [4] A direct method for the synthesis of nucleoside 5'-methylenebis(phosphonate)s from nucleosides
    Kalek, M
    Jemielity, J
    Stepinski, J
    Stolarski, R
    Darzynkiewicz, E
    TETRAHEDRON LETTERS, 2005, 46 (14) : 2417 - 2421
  • [5] SPIN-LABELED NUCLEOSIDES, NUCLEOSIDE-5'-MONOPHOSPHATE,DIPHOSPHATE AND TRIPHOSPHATE
    PETROV, AI
    SUKHORUKOV, BI
    BIOFIZIKA, 1975, 20 (06): : 965 - 966
  • [6] Syntheses of 5′-Nucleoside Monophosphate Derivatives with Unique Aminal, Hemiaminal, and Hemithioaminal Functionalities: A New Class of 5′-Peptidyl Nucleotides
    De, Swarup
    Groaz, Elisabetta
    Margamuljana, Lia
    Herdewijn, Piet
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (24) : 8167 - 8180
  • [7] Novel anti-HIV prodrugs based on nucleoside phosphonate derivatives
    Pokrovsky, A
    Pronayeva, T
    Fedyuk, N
    Plyasunova, O
    Gashnikova, N
    Khandazhinskaya, A
    Shirokova, E
    ANTIVIRAL RESEARCH, 2002, 53 (03) : A69 - A69
  • [8] Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues
    Mohamed, Bemba Sidi
    Perigaud, Christian
    Mathe, Christophe
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 251 - 256
  • [9] Novel acyclic nucleoside phosphonate analogues as potent and selective anti-HBV agents
    Ying, C
    Holy, A
    Hocková, D
    De Clercq, E
    Neyts, J
    ANTIVIRAL RESEARCH, 2004, 62 (02) : A45 - A45
  • [10] L-nucleoside analogues as a novel class of HBV drugs
    Cheng, YC
    ANTIVIRAL THERAPY, 2002, 7 (04) : L83 - L83