Recent Developments in the Synthesis and Applications of C5-Substituted Pyrimidine Nucleosides and Nucleotides

被引:0
|
作者
Kore, Anilkumar R. [1 ]
Charles, Irudaya [1 ]
机构
[1] Life Technol Corp, Bioorgan Chem Div, Austin, TX 78744 USA
关键词
Click chemistry; Organometallic coupling; C5-halopyrimidines; C5-substituted pyrimidine nucleosides and nucleotides; HERPES-SIMPLEX-VIRUS; CLICK CHEMISTRY; EFFICIENT METHOD; POLYMERASE INCORPORATION; NUCLEIC-ACIDS; MAJOR GROOVE; SIDE-CHAINS; DNA; 2'-DEOXYURIDINE; TRIPHOSPHATES;
D O I
10.2174/138527212803251622
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C5-position in pyrimidine nucleosides and nucleotides is an invaluable anchor point for tagging diverse kind of labels like haptens, dyes and signaling molecules. Oligonucleotides with such C5-modified pyrimidine nucleosides and nucleotides are being used in molecular genetics and next generation nucleic acid sequencing as indispensable diagnostic tools. In view of their requirement in a wide range of primers and probes, chemistry synthesis and manufacture of C5-modified substituted pyrimidines had elicited continued interest over the last several decades. These diverse classes of molecules also have pharmaceuticals significance. The objective of this review is to capture the recent strategies available to synthesize C5-modified pyrimidine nucleosides and nucleotides that include organometallic, "Click" and photochemistry.
引用
收藏
页码:1996 / 2013
页数:18
相关论文
共 50 条
  • [31] Microwave-assisted C-5 iodination of substituted pyrimidinones and pyrimidine nucleosides
    Paolini, L
    Petricci, E
    Corelli, F
    Botta, M
    SYNTHESIS-STUTTGART, 2003, (07): : 1039 - 1042
  • [32] Synthesis of pyrimidine nucleosides and nucleotides containing exo-4-Selenium
    Sheng, Jia
    Salon, Jozef
    Huang, Zhen
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [33] Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides
    Johar, M
    Manning, T
    Kunimoto, DY
    Kumar, R
    BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (24) : 6663 - 6671
  • [34] SYNTHESIS OF 5-MERCAPTOCYTOSINE NUCLEOSIDES AND NUCLEOTIDES
    SOLAN, VC
    SZEKERES, GL
    RYU, EK
    KUNG, H
    HO, YK
    BARDOS, TJ
    NUCLEOSIDES & NUCLEOTIDES, 1983, 2 (05): : 419 - 434
  • [35] Nucleosides and nucleotides.: 185.: Synthesis and biological activities of 4′α-C-branched-chain sugar pyrimidine nucleosides
    Nomura, M
    Shuto, S
    Tanaka, M
    Sasaki, T
    Mori, S
    Shigeta, S
    Matsuda, A
    JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (15) : 2901 - 2908
  • [36] Novel Antiviral C5-Substituted Pyrimidine Acyclic Nucleoside Phosphonates Selected as Human Thymidylate Kinase Substrates
    Topalis, Dimitri
    Pradere, Ugo
    Roy, Vincent
    Caillat, Christophe
    Azzouzi, Ahmed
    Broggi, Julie
    Snoeck, Robert
    Andrei, Graciela
    Lin, Jay
    Eriksson, Staffan
    Alexandre, Julie A. C.
    El-Amri, Chahrazade
    Deville-Bonne, Dominique
    Meyer, Philippe
    Balzarini, Jan
    Agrofoglio, Luigi A.
    JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) : 222 - 232
  • [37] Synthesis of C5-substituted AE-bicyclic analogues of lycoctonine, inuline and methyllycaconitine
    Grangier, G
    Trigg, WJ
    Lewis, T
    Rowan, MG
    Potter, BVL
    Blagbrough, IS
    TETRAHEDRON LETTERS, 1998, 39 (08) : 889 - 892
  • [38] PYRIDO[2,3-D]PYRIMIDINE NUCLEOSIDES - SYNTHESIS VIA CYCLIZATION OF C-5-SUBSTITUTED CYTIDINES
    BERGSTROM, DE
    INOUE, H
    REDDY, PA
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11): : 2174 - 2178
  • [39] Modifications at the C(5) position of pyrimidine nucleosides
    Kozak, Witold
    Demkowicz, Sebastian
    Dasko, Mateusz
    Rachon, Janusz
    Rak, Janusz
    RUSSIAN CHEMICAL REVIEWS, 2020, 89 (03) : 281 - 310
  • [40] Synthesis of C5-substituted AE-bicyclic analogues of lycoctonine, inuline and methyllycaconitine
    Grangier, G.
    Trigg, W. J.
    Lewis, T.
    Rowan, M. G.
    Tetrahedron Letters, 39 (08):