SYNTHESIS OF 5-ALKOXYMETHYL DERIVATIVES OF 3'-AMINO-2',3'-DIDEOXYURIDINE AND EVALUATION OF THEIR ACTIVITY AGAINST HIV AND CANCER

被引：14
|
作者：
MOTAWIA, MS
ABDELMEGIED, AES
PEDERSEN, EB
NIELSEN, CM
EBBESEN, P
机构：
[1] ODENSE UNIV,DEPT CHEM,CAMPUSVEJ 55,DK-5230 ODENSE,DENMARK
[2] DANISH CANC SOC,DEPT VIRUS & CANC,DK-8000 AARHUS C,DENMARK
[3] STATENS SERUMINST,DEPT ENTEROVIRUS,RETROVIRUS LAB,DK-2300 COPENHAGEN,DENMARK
来源：
ACTA CHEMICA SCANDINAVICA | 1992年 / 46卷 / 01期
关键词：
D O I：
10.3891/acta.chem.scand.46-0077
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：
5-Alkoxymethyluracils 2a-c have been prepared by acid-catalyzed etherification of 5-hydroxymethyluracil (1). Compounds 1, 2a-c, 5-methoxymethyl- and 5-benzyloxymethyl-uracil were silylated and coupled with 1,5-di-O-acetyl-3-phthalimido-2,3-dideoxy-beta-D-erythro-pentofuranose (3), in the presence of trimethylsilyl triflate as a catalyst, to give the corresponding 3'-phthalimido-2',3'-dideoxynucleosides 5a-f and 6 which on treatment with 33% methylamine-ethanol afforded the corresponding 3'-amino-2',3'-dideoxynucleosides 7a-f and 8 in high yields. Compound 7d showed colony inhibition when tested against human epidermoid cervical cancer cells. Nucleosides 5a-e, 7a-f and 8 did not show any significant activity against HIV-1.
引用
收藏
页码：77 / 81
页数：5
相关论文
共 50 条
  • [1] 2,3-DIDEOXY-3-TETRABROMOPHTHALIMIDO-D-PENTOSES IN THE SYNTHESIS OF 3'-AMINO-2',3'-DIDEOXYURIDINE
    MOTAWIA, MS
    JACOBSEN, JP
    PEDERSEN, EB
    CHEMICA SCRIPTA, 1989, 29 (01): : 51 - 55
  • [2] A synthesis of 5′-amino-3′,5′-dideoxyuridine
    Bender, DM
    Hennings, DD
    Williams, RM
    SYNTHESIS-STUTTGART, 2000, (03): : 399 - 402
  • [3] Synthesis and biological evaluation of some 5-nitro- and 5-amino derivatives of 2′-deoxycytidine, 2′,3′-dideoxyuridine, and 2′,3′-dideoxycytidine
    Colacino, E
    Sindona, G
    Gosselin, G
    Mathé, C
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (11): : 2013 - 2026
  • [4] AMINONUCLEOSIDES AND THEIR DERIVATIVES .11. SYNTHESIS OF 3'-AMINO-2',3'-DIDEOXYNUCLEOSIDE 5'-TRIPHOSPHATES
    ZAITSEVA, VE
    DYATKINA, NB
    KRAYEVSKY, AA
    SKAPTSOVA, NV
    TURINA, OV
    GNUCHEV, NV
    GOTTIKH, BP
    AZHAYEV, AV
    BIOORGANICHESKAYA KHIMIYA, 1984, 10 (05): : 670 - 680
  • [5] 5-CHLORO-SUBSTITUTED DERIVATIVES OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYURIDINE, 3'-FLUORO-2',3'-DIDEOXYURIDINE AND 3'-AZIDO-2',3'-DIDEOXYURIDINE AS ANTI-HIV AGENTS
    BALZARINI, J
    VANAERSCHOT, A
    HERDEWIJN, P
    DECLERCQ, E
    BIOCHEMICAL PHARMACOLOGY, 1989, 38 (06) : 869 - 874
  • [6] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF 5-TRIFLUOROMETHYL-5'-AZIDO-2',5'-DIDEOXYURIDINE AND 5-TRIFLUOROMETHYL-5'-AMINO-2',5'-DIDEOXYURIDINE
    LIN, TS
    CHAI, C
    PRUSOFF, WH
    JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (07) : 915 - 918
  • [7] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF 5-TRIFLUOROMETHYL-5'-AZIDO-2',5'-DIDEOXYURIDINE AND 5-TRIFLUOROMETHYL-5'-AMINO-2',5'-DIDEOXYURIDINE
    LIN, TS
    PRUSOFF, WH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1975, 170 (AUG24): : 51 - 51
  • [8] Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate "ProTide' derivatives
    Mehellou, Youcef
    McGuigan, Christopher
    Brancale, Andrea
    Balzarini, Jan
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (13) : 3666 - 3669
  • [9] Synthesis of oligonucleotides with 3′-terminal 5-(3-acylamidopropargyl)-3′-amino-2′,3′-dideoxyuridine residues and their reactivity in single-nucleotide steps of chemical replication
    Baumhof, P
    Griesang, N
    Bächle, M
    Richert, C
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03): : 1060 - 1067
  • [10] SYNTHESIS AND ANTI-HIV ACTIVITY OF 5-ALKOXYMETHYL-3'-AZIDO-2',3'-DIDEOXYURIDINES
    ABDELMEGIED, AES
    HANSEN, P
    PEDERSEN, EB
    NIELSEN, C
    NIELSEN, CM
    ARCHIV DER PHARMAZIE, 1993, 326 (07) : 377 - 381
12345