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

Autor(en): SEELA, F
GUMBIOWSKI, R
Stichwörter: 2',3'-DIDEOXYRIBONUCLEOSIDES; 2'-DEOXYRIBONUCLEOSIDES; 2,3-DIDEOXY-D-GLYCERO-PENTOFURANOSYL CHLORIDE; 2-C>PYRIDINE 2',3'-DIDEOXYRIBONUCLEOSIDES; 3-D>PYRIMIDINE; 5'-TRIPHOSPHATES; ACID; Chemistry; Chemistry, Multidisciplinary; FACILE SYNTHESIS; GLYCOSYLATION; HIV INHIBITION; HIV-1 REVERSE-TRANSCRIPTASE; IMIDAZO[1,2-A]PYRIMIDINES; PYRIMIDINE-BASES; PYRROLO<2
Erscheinungsdatum: 1992
Herausgeber: VCH PUBLISHERS INC
Journal: LIEBIGS ANNALEN DER CHEMIE
Ausgabe: 7
Startseite: 679
Seitenende: 686
Zusammenfassung: 
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.
ISSN: 01702041

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