Synthesis of 3'-deoxy-3' and 5'-deoxy-5'-[4-(purin-9-yl/pyrimidin-1-yl)methyl-1,2,3-triazol-1-yl]thymidine via 1,3-dipolar cycloaddition

被引：17
|
作者：
Lazrek, HB
Taourirte, M
Oulih, T
Kabbaj, Y
Barascut, JL
Imbach, JL
Almasoudi, NA
Pfleiderer, W
机构：
[1] UNIV KONSTANZ,FAC CHEM,D-7750 CONSTANCE,GERMANY
[2] UNIV MONTPELLIER 2,CHIM BIOORGAN LAB,F-34095 MONTPELLIER 5,FRANCE
来源：
NUCLEOSIDES & NUCLEOTIDES | 1997年 / 16卷 / 7-9期
关键词：
IMMUNODEFICIENCY-VIRUS INFECTIONS; ANTIVIRAL THERAPY;
D O I：
10.1080/07328319708006135
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：
Synthesis of new 3'-deoxy-3' and 5'-deoxy-5'-[(4-(purin-9-yl/pyrimidin-1-yl)methyl-1,2,3- 8a-g, 10a-g from 3'-azido-3'-deoxy-5'-O-monomethoxytrityl-thymidine and 5'-azido-5'-deoxythymidine respectively are described. The key step is the 1,3-dipolar cycloaddition between the azido group and N-9/N-1-propargylpurine/pyrimidine derivatives.
引用
收藏
页码：1073 / 1077
页数：5
相关论文
共 50 条
  • [1] Synthesis of 3′-deoxy-3′-[4-(pyrimidin-1-yl)methyl-1,2,3-triazol-1-yl]thymidine via 1,3-dipolar cycloaddition
    Tourirte, M
    Oulih, T
    Lazrek, HB
    Barascut, JL
    Imbach, JL
    Almasoudi, NA
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (11): : 1985 - 1993
  • [2] ISONUCLEOSIDES .1. PREPARATION OF METHYL 2-DEOXY-2-(PURIN-9-YL)ARABINOFURANOSIDES AND METHYL 3-DEOXY-3-(PURIN-9-YL)XYLOFURANOSIDES
    MONTGOMERY, JA
    CLAYTON, SD
    THOMAS, HJ
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (13): : 1923 - 1927
  • [3] Efficient access to 3′-deoxy-3′-(4-substituted-1,2,3-triazol-1-yl)-thymidine derivatives via ligand-promoted CuAAC
    Garlatti, Laura
    Huet, Raphael
    Alvarez, Karine
    TETRAHEDRON, 2021, 92
  • [4] SYNTHESIS OF 2-(PYRIMIDIN-1-YL)-AMINO AND 2-(PURIN-9-YL)-2-AMINO ACIDS
    NISHITANI, T
    IWASAKI, T
    MUSHIKA, Y
    MIYOSHI, M
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (12): : 2019 - 2023
  • [5] CHEMOENZYMATIC SYNTHESIS OF 3′-DEOXY-3′-(4-SUBSTITUTED-TRIAZOL-1-YL)-5-METHYLURIDINE
    Arya, Anu
    Mathur, Divya
    Tyagi, Abhilash
    Kumar, Rajesh
    Kumar, Vinod
    Olsen, Carl E.
    Saxena, Rajendra K.
    Prasad, Ashok K.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2013, 32 (12): : 646 - 659
  • [6] Microwave-assisted 1,3-dipolar cycloaddition.: Synthesis of substituted 9-(1,2,3-triazol-1-yl)acridines
    Veverková, E
    Toma, S
    CHEMICAL PAPERS-CHEMICKE ZVESTI, 2005, 59 (5-6): : 350 - 353
  • [7] SYNTHESIS OF 3'-(1,2,3-TRIAZOL-1-YL)-3'-DEOXYTHYMIDINES
    HABICH, D
    BARTH, W
    ROSNER, M
    HETEROCYCLES, 1989, 29 (11) : 2083 - 2088
  • [8] 4-{4-[(4-Oxoquinazolin-3-yl)methyl]-1H-1,2,3-triazol-1-yl}butyl acetate
    Ouahrouch, Abdelaaziz
    Taourirte, Moha
    Lazrek, Hassan B.
    El Azhari, Mohamed
    Saadi, Mohamed
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3191 - U1238
  • [9] Design and Synthesis of Various 5′-Deoxy-5′-(4-Substituted-1,2,3-Triazol-1-yl)-Uridine Analogues as Inhibitors of Mycobacterium tuberculosis Mur Ligases
    Hervin, Vincent
    Arora, Ritu
    Rani, Jyoti
    Ramchandran, Srinivasan
    Bajpai, Urmi
    Agrofoglio, Luigi A.
    Roy, Vincent
    MOLECULES, 2020, 25 (21):
  • [10] Synthesis of 4-(1,2,3-triazol-1-yl)-L-phenylalanines
    Bagra, Nitin
    Jain, Rahul
    SYNTHETIC COMMUNICATIONS, 2022, 52 (08) : 1176 - 1183
12345