SYNTHESIS OF 2-O-ETHYL ANALOGS OF 3'-AZIDO-2',3'-DIDEOXYURIDINE AND 3'-FLUORO-2',3'-DIDEOXYURIDINES AND EVALUATION OF THEIR BIOLOGICAL-ACTIVITY AGAINST HIV

被引：5
作者：
ABDELBARY, HM
ABDELRAHMAN, AAH
PEDERSEN, EB
NIELSEN, C
机构：
[1] ODENSE UNIV,DEPT CHEM,DK-5230 ODENSE M,DENMARK
[2] STATENS SERUM INST,DEPT VIROL,RETROVIRUS LAB,DK-2300 COPENHAGEN,DENMARK
来源：
MONATSHEFTE FUR CHEMIE | 1995年 / 126卷 / 6-7期
关键词：
NUCLEOSIDES; CONVERGENT SYNTHESIS OF; URIDINES; 2-O-ETHYL; 2'; 3'-DIDEOXY-3'-FLUORO; AZT ANALOGS; HUMAN IMMUNODEFICIENCY VIRUS; HERPES SIMPLEX VIRUS;
D O I：
10.1007/BF00807175
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
2-O-Ethyluracil and 2-O-ethylthymine were silylated with 1,1,1,3,3,3-hexamethyldisilazane and condensed in the presence of TMS triflate with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside, 3-azido-2,3-dideoxy-D-erythro-pentofuranoside and 2,3-dideoxy-3-phthalimido-beta-D-erythro-pentofuranose furanose derivatives to give the corresponding 2-O-ethyl nucleosides. Deprotection with saturated methanolic ammonia afforded the 2',3'-dideoxy-3'-fluoro-2-O-ethyluridines whereas 3'-azido-2',3'-dideoxy-3-O-ethyluridine was obtained by deprotection with tetrabutylammonium fluoride in tetrahydrofuran. 3'-Amino-2',3'-dideoxy-3-O-ethyluridine could be obtained only by treatment of the corresponding 3'-azido nucleoside with triphenylphosphine in pyridine. 3'-Deoxy-2-O-ethyl-3'-fluorothymidine (6b) showed moderate activity against HIV-1.
引用
收藏
页码：811 / 817
页数：7
相关论文
共 50 条
  • [21] SYNTHESIS AND ANTIVIRAL EVALUATION OF QUINAZOLINE, THIENO-[2,3-D]PYRIMIDINE, AND LUMAZINE ANALOGS OF 3'-FLUORO-3'-DEOXYTHYMIDINE (FLT)
    ELBARBARY, AA
    ELBROLLOSY, NR
    ABDELBARY, HM
    PEDERSEN, EB
    STEIN, P
    NIELSEN, C
    LIEBIGS ANNALEN, 1995, (07): : 1371 - 1375
  • [22] The synthesis of new acyclic analogs of 3-phenacyluridine and comparative evaluation of their in vivo biological activity
    Novakov, Ivan A.
    Brunilina, Leila L.
    Kirillov, Ivan A.
    Nawrozkij, Maxim B.
    Robinovich, Mariya D.
    Titova, Evgeniya S.
    Sheikin, Dmitry S.
    Ruchko, Evsey A.
    Pavlova, Alla, V
    Kotlyarova, Anastasiya A.
    Tolstikova, Tatyana G.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (06) : 769 - 775
  • [23] CONVERGENT SYNTHESIS OF 2',3'-DIDEOXY-3'-MERCAPTO NUCLEOSIDES - POTENTIAL ANTI-HIV AGENTS
    ELBARBARY, AA
    KHODAIR, AI
    PEDERSEN, EB
    NIELSEN, C
    MONATSHEFTE FUR CHEMIE, 1994, 125 (8-9): : 1017 - 1025
  • [24] Synthesis of 2',3'-dideoxy-2'-fluoro-4'-thionucleosides from a fluoroxanthate
    Jean-Baptiste, Laeetitia
    Lefebvre, Pierre
    Pfund, Emmanuel
    Lequeux, Thierry
    SYNLETT, 2008, (06) : 817 - 820
  • [25] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF CARBOCYCLIC 2',3'-DIDEOXY-3'-FLUORO NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS
    NAKAYAMA, T
    MATSUMURA, Y
    MORIZAWA, Y
    YASUDA, A
    UCHIDA, K
    TAKASE, H
    MURAKAMI, Y
    ATARASHI, S
    IKEUCHI, T
    OSADA, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (02) : 183 - 187
  • [26] Synthesis and antiviral evaluation of α-D-2′,3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides
    Yamada, Kohei
    Hayakawa, Hiroyuki
    Sakata, Shinji
    Ashida, Noriyuki
    Yoshimura, Yuichi
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (20) : 6013 - 6016
  • [27] Stereoselective Synthesis of PSI-352938: A β-D-2′-Deoxy-2′-α-fluoro-2′-β-C-methyl-3′,5′-cyclic Phosphate Nucleotide Prodrug for the Treatment of HCV
    Reddy, P. Ganapati
    Chun, Byoung-Kwon
    Zhang, Hai-Ren
    Rachakonda, Suguna
    Ross, Bruce S.
    Sofia, Michael J.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) : 3782 - 3790
  • [28] Synthesis and anticancer activity of 3′-[4-fluoroaryl-(1,2,3-triazol-1-yl)]-3′-deoxythymidine analogs and their phosphoramidates
    Kleczewska, Natalia
    Ruszkowski, Piotr
    Singh, Aleksandra
    Trznadel, Roksana
    Celewicz, Lech
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2019, 38 (09) : 605 - 641
  • [29] SYNTHESIS OF 2',3'-DIDEOXY-3'-FLUOROURIDINES WITH POTENTIAL ANTI-HIV ACTIVITY ACCORDING TO NEURAL-NETWORK CALCULATIONS
    SOFAN, MA
    ABDELMEGIED, AES
    PEDERSEN, MB
    PEDERSEN, EB
    NIELSEN, C
    SYNTHESIS-STUTTGART, 1994, (05): : 516 - 520
  • [30] Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2′,3′-dideoxy-2′,2′-difluoro-4′-azanucleosides
    Martinez-Montero, Saul
    Fernandez, Susana
    Sanghvi, Yogesh S.
    Theodorakis, Emmanuel A.
    Detorio, Mervi A.
    Mcbrayer, Tamara R.
    Whitaker, Tony
    Schinazi, Raymond F.
    Gotor, Vicente
    Ferrero, Miguel
    BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (23) : 6885 - 6893
12345