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
  • [41] First and facile enzymatic synthesis of β-fucosyl-containing disaccharide nucleosides through β-galactosidase-catalyzed regioselective glycosylation
    Yan, Li-Qiang
    Li, Ning
    Zong, Min-Hua
    JOURNAL OF BIOTECHNOLOGY, 2013, 164 (02) : 371 - 375
  • [42] New modified 2-aminobenzimidazole nucleosides: Synthesis and evaluation of their activity against herpes simplex virus type 1
    Kharitonova, Maria I.
    Denisova, Alexandra O.
    Andronova, Valeria L.
    Kayushin, Alexei L.
    Konstantinova, Irina D.
    Kotovskaya, Svetlana K.
    Galegov, Georgiy A.
    Charushin, Valery N.
    Miroshnikov, Anatoly I.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (11) : 2484 - 2487
  • [43] Synthesis and anticancer activity of novel C6-piperazine substituted purine steroid-nucleosides analogues
    Huang, Li-Hua
    Xu, Hong -De
    Yang, Zhuo-Ya
    Zheng, Yong-Fei
    Liu, Hong-Min
    STEROIDS, 2014, 82 : 1 - 6
  • [44] Stereocontrolled synthesis of diene and enyne sugar-modified nucleosides and their interaction with S-adenosyl-L-homocysteine hydrolase
    Wnuk, SF
    Sacasa, PR
    Crain, LN
    Lewandowska, E
    Zhang, JS
    Borchardt, RT
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (5-8): : 783 - 785
  • [45] Synthesis and Antiviral Activity of Novel Thieno[2,3-d]pyrimidine Hydrazones and Their C-Nucleosides
    R. R. Khattab
    A. A. Hassan
    O. M. Kutkat
    K. M. Abuzeid
    N. A. Hassan
    Russian Journal of General Chemistry, 2019, 89 : 1707 - 1717
  • [46] Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: A new class of antiviral acyclic nucleoside phosphonates
    Choo, Hyunah
    Beadle, James R.
    Chong, Youhoon
    Trahan, Julissa
    Hostetler, Karl Y.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (04) : 1771 - 1779
  • [47] Facile Synthesis of Fluorinated Benzofuro- and Benzothieno[2,3-b]pyridines, α-Carbolines and Nucleosides Containing the α-Carboline Framework
    Iaroshenko, Viktor O.
    Wang, Yan
    Zhang, Biao
    Volochnyuk, Dmitriy
    Sosnovskikh, Vyacheslav Ya.
    SYNTHESIS-STUTTGART, 2009, (14): : 2393 - 2402
  • [48] Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur-Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation
    Li, Jian-Ping
    Tuo, Hao-Ran
    Xie, Ming-Sheng
    Kang, Bo
    Qu, Gui-Rong
    Guo, Hai-Ming
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (01) : 128 - 132
  • [49] Synthesis and regioselective deacylation studies on peracylated 2′-azido arabino- and ribo-thymine nucleosides: Towards 5′-O,2′-N-linked oligonucleotides
    Sharma, Deepti
    Khandelwal, Anuj
    Sharma, Raman K.
    Bhatia, Sumati
    Reddy, L. Chandrashekar
    Olsen, Carl E.
    Wengel, Jesper
    Parmar, Virinder S.
    Prasad, Ashok K.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2009, 48 (12): : 1712 - 1720
  • [50] 7-Deaza-2,8-diazaadenine containing oligonucleotides: synthesis, ring opening and base pairing of 7-halogenated nucleosides
    Lin, WQ
    Xu, KY
    Seela, F
    TETRAHEDRON, 2005, 61 (31) : 7520 - 7527
12345