A novel class of modified nucleosides: Synthesis of alkylidene isoxazolidinyl nucleosides containing thymine

被引：18
|
作者：
Piperno, Anna
Rescifina, Antonio
Corsaro, Antonino
Chiacchio, Maria A.
Procopio, Antonio
Romeo, Roberto
机构：
[1] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy
[2] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[3] Magna Graecia Univ Catanzaro, Dipartimento Sci Farmaco Biol, I-88021 Roccelletta Di Borgia, Cz, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 09期
关键词：
dipolar cycloaddition; nucleosides; nitrogen heterocycles; oxygen heterocycles;
D O I：
10.1002/ejoc.200600817
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of hitherto unknown 1-[3-(hydroxymethyl)-2-methyl-4-methyleneisoxazolidin-5-yl]thymine (5), 1-{(Z)-[3(hydroxymethyl)-2-methylisoxazolidin-4-ylidene]methyl}- thymine (6), and 1-[(E)-[3-(hydroxymethyl)-2-methylisoxazolidin-5-ylidene]methyl}thymine (7) is described. The first compound can be regarded as a N,O-analogue of Entecavir and DMDC, which contains thymine as a nucleobase. The key allenic nucleobase was prepared in good yields starting from 2,3-dibromopropene. The subsequent 1,3-dipolar cycloaddition proceeded with good site selectivity to give 5 and regioisomeric nucleosides 6 and 7. ((c) Wiley-VCH Verlag GmbH & Co.
引用
收藏
页码：1517 / 1521
页数：5
相关论文
共 50 条
  • [1] Enantioselective synthesis of isoxazolidinyl thymine and cytosine nucleosides
    Xiang, YJ
    Gong, YX
    Zhao, K
    TETRAHEDRON LETTERS, 1996, 37 (28) : 4877 - 4880
  • [2] Synthesis of [3.3.0] bicyclic isoxazolidinyl nucleosides
    Xiang, YJ
    Schinazi, RF
    Zhao, K
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (13) : 1475 - 1478
  • [3] THE SYNTHESIS OF THYMINE NUCLEOSIDES
    VISSER, DW
    GOODMAN, I
    DITTMER, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (05) : 1926 - 1928
  • [4] Synthesis of 5-Alkynyl Isoxazolidinyl Nucleosides
    Romeo, Roberto
    Giofre, Salvatore Vincenzo
    Iaria, Daniela
    Sciortino, Maria Teresa
    Ronsisvalle, Simone
    Chiacchio, Maria Assunta
    Scala, Angela
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (28) : 5690 - 5695
  • [5] Diastereoselective synthesis of D-xylo-isoxazolidinyl nucleosides
    Hyrosova, Eva
    Medvecky, Michal
    Fisera, Lubor
    Hametner, Christian
    Froehlich, Johannes
    Marchetti, Martina
    Allmaier, Gunter
    TETRAHEDRON, 2008, 64 (14) : 3111 - 3118
  • [6] Enantioselective synthesis of isoxazolidinyl nucleosides containing uracil, 5-fluorouracil, thymine and cytosine as new potential anti-HIV drugs
    Chiacchio, U
    Corsaro, A
    Iannazzo, D
    Piperno, A
    Pistara, V
    Procopio, A
    Rescifina, A
    Romeo, G
    Romeo, R
    Siciliano, MCR
    Valveri, E
    ARKIVOC, 2002, : 159 - 167
  • [7] PYRIMIDINE NUCLEOSIDES .1. A NEW ROUTE FOR THE SYNTHESIS OF THYMINE NUCLEOSIDES
    FOX, JJ
    YUNG, N
    DAVOLL, J
    BROWN, GB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (10) : 2117 - 2122
  • [8] MODIFIED NUCLEOSIDES .5. SYNTHESIS OF PYRAZOLE NUCLEOSIDES
    AKHREM, AA
    GARBUZ, NI
    KVASYUK, EI
    MIKHAILOPULO, IA
    ZHURNAL OBSHCHEI KHIMII, 1976, 46 (06): : 1394 - 1403
  • [9] MEDI 329-Seven-membered ring sugar nucleosides: Synthesis and first antiviral evaluation of a novel class of modified nucleosides
    Leroy, Frederic
    Bouisset, Tony
    Chaves, Dominique
    Dukhan, David
    Gosselin, Gilles
    Meillon, Jean-Christophe
    Storer, Richard
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [10] NUCLEOSIDES AND RELATED COMPOUNDS .3. SYNTHESIS OF THYMINE NUCLEOSIDES THROUGH SILYLPYRIMIDINE COMPOUNDS
    WITTENBURG, E
    CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (03): : 1095 - +
12345