IMIDAZO[1,2-A]PYRIMIDINE 2'-DEOXYRIBONUCLEOSIDE AND 2',3'-DIDEOXYRIBONUCLEOSIDE - GLYCOSYLATION OF THE NUCLEOBASE ANION

被引：0
|
作者：
SEELA, F
GUMBIOWSKI, R
机构：
来源：
LIEBIGS ANNALEN DER CHEMIE | 1992年 / 07期
关键词：
IMIDAZO[1,2-A]PYRIMIDINES; 2'-DEOXYRIBONUCLEOSIDES; 2'; 3'-DIDEOXYRIBONUCLEOSIDES; GLYCOSYLATION; HIV INHIBITION;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of the imidazo[1,2-a]pyrimidine 2'-deoxyribonucleosides 2a and 3a related to 2'-deoxyguanosine or 2'deoxyinosine is described. Glycosylation of the nucleobase anion of 5 with 2'-deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl chloride (6) yielded stereoselectively the N-1 beta-D-deoxyribofuranoside 7. Under the same conditions the 2',3'-dideoxyrihalogenoses 11 and 14 were employed to afford anomeric mixtures of glycosylation products (12, 13 and 15, 16). The glycosylation products obtained from the 2'-(deoxyribo- and 2',3'-dideoxyribo halides were then converted into the final nucleosides (2a,b and 3a,b). The inhibitory activity of the imidazo[1,2-a]pyrimidine 2',3'-dideoxynucleoside 5'-triphosphates 28a and 28b against HIV reverse transcriptase was tested.
引用
收藏
页码：679 / 686
页数：8
相关论文
共 50 条
  • [21] Effect of imidazo[1,2-a]pyrimidine derivatives on leukocyte function
    Vidal, A
    Ferrándiz, ML
    Ubeda, A
    Acero-Alarcón, A
    Sepulveda-Arques, J
    Alcaraz, MJ
    INFLAMMATION RESEARCH, 2001, 50 (06) : 317 - 320
  • [22] Heterocyclization Reactions of Imidazo[1,2-a]pyrimidine Analogues (A Review)
    He, L.
    Liu, J.
    Zhao, H. L.
    Kang, C. M.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (SUPPL 1) : S20 - S47
  • [23] 2-(2-Furyl)imidazo[1,2-a]pyrimidine.: Synthesis and reactions of electrophilic substitution
    Saldabol, N.
    Popelis, J.
    Lando, O.
    Slavinska, V.
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2006, (04): : 565 - 570
  • [24] PYRIMIDINES .2. SYNTHESIS OF IMIDAZO[1,2-A]- AND PYRIMIDO[1,2-A]-PYRIMIDINEDIONES
    ABARCA, B
    JIMENEZ, M
    JONES, G
    SORIANO, C
    JOURNAL OF CHEMICAL RESEARCH-S, 1986, (11): : 395 - 395
  • [25] Fluorescent property of 3-hydroxymethyl imidazo[1,2-a]pyridine and pyrimidine derivatives
    Stephania Velázquez-Olvera
    Héctor Salgado-Zamora
    Manuel Velázquez-Ponce
    Elena Campos-Aldrete
    Alicia Reyes-Arellano
    Cuauhtémoc Pérez-González
    Chemistry Central Journal, 6
  • [26] Fluorescent property of 3-hydroxymethyl imidazo [1,2-a]pyridine and pyrimidine derivatives
    Velazquez-Olvera, Stephania
    Salgado-Zamora, Hector
    Velazquez-Ponce, Manuel
    Campos-Aldrete, Elena
    Reyes-Arellano, Alicia
    Perez-Gonzalez, Cuauhtemoc
    CHEMISTRY CENTRAL JOURNAL, 2012, 6
  • [27] NEW TRICYCLIC COMPOUNDS - PYRIDO[2',3'-4,5]IMIDAZO[1,2-A]PYRIMIDINES AND PYRIDO[3',2'-4,5]IMIDAZO[1,2-A]PYRIMIDINES
    DESCOURS, D
    FESTAL, D
    HETEROCYCLES, 1990, 31 (02) : 259 - 265
  • [28] Synthesis of 3-fluoro-2-(diethoxyphosphoryl)imidazo[1,2-a]pyridine
    Aksinenko, Alexei Yu.
    Goreva, Tatyana V.
    Epishina, Tatyana A.
    Sokolov, Vladimir B.
    JOURNAL OF FLUORINE CHEMISTRY, 2012, 137 : 105 - 107
  • [29] Palladium-catalyzed regioselective arylation of imidazo[1,2-a]pyrimidine
    Li, WJ
    Nelson, DP
    Jensen, MS
    Hoerrner, RS
    Javadi, GJ
    Cai, D
    Larsen, RD
    ORGANIC LETTERS, 2003, 5 (25) : 4835 - 4837
  • [30] A facile access to 2-CF3-imidazo[1,2-a]pyridines
    Krasovsky, AL
    Nenajdenko, VG
    Balenkova, ES
    SYNTHESIS-STUTTGART, 2002, (10): : 1379 - 1384
12345