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Titolo:
Synthesis and biological activity of 4-substituted 1-[1-(2-hydroxyethoxy)methyl-1,2,3-triazol-(4&5)-ylmethyl]-1H-pyrazolo[3,4-d]pyrimidines
Autore:
Moukha-Chafiq, O; Taha, ML; Lazrek, HB; Pannecouque, C; Witvrouw, M; De Clercq, E; Barascut, JL; Imbach, JL;
Indirizzi:
Fac Sci, Chim Bioorgan Lab, Agadir, Morocco Fac Sci Agadir MoroccoFac Sci, Chim Bioorgan Lab, Agadir, Morocco Fac Sci 1, Chim Bioorgan Lab, Marrakech, Morocco Fac Sci 1 Marrakech Morocco ci 1, Chim Bioorgan Lab, Marrakech, Morocco Catholic Univ Louvain, Rega Inst Med Res, B-3000 Louvain, Belgium CatholicUniv Louvain Louvain Belgium B-3000 es, B-3000 Louvain, Belgium Univ Montpellier 2, Chim Bioorgan Lab, F-34095 Montpellier 5, France Univ Montpellier 2 Montpellier France 5 b, F-34095 Montpellier 5, France
Titolo Testata:
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
fascicolo: 10-11, volume: 20, anno: 2001,
pagine: 1797 - 1810
SICI:
1525-7770(2001)20:10-11<1797:SABAO4>2.0.ZU;2-2
Fonte:
ISI
Lingua:
ENG
Soggetto:
ANALOGS; ACYCLONUCLEOSIDES; GLYCOSYLATION; NUCLEOSIDES; ASSAY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
24
Recensione:
Indirizzi per estratti:
Indirizzo: Taha, ML Fac Sci, Chim Bioorgan Lab, Agadir, Morocco Fac Sci Agadir Morocco Sci, Chim Bioorgan Lab, Agadir, Morocco
Citazione:
O. Moukha-Chafiq et al., "Synthesis and biological activity of 4-substituted 1-[1-(2-hydroxyethoxy)methyl-1,2,3-triazol-(4&5)-ylmethyl]-1H-pyrazolo[3,4-d]pyrimidines", NUCLEOS NUC, 20(10-11), 2001, pp. 1797-1810

Abstract

The chemical synthesis of some 4-substituted 1-[1-(2-hydroxyethoxy)-methyl-1,2,3-triazol-(4 and 5)-ylmethyl]-1H-pyrazolo[3,4-d]pyrimidines 12a,b, 13a,b and 14-23 as acyclic nucleosides is described. Treatment of (2-acetoxyethoxy)methyl bromide with sodium azide afforded (2-acetoxyethoxy)methylazide9. The heterocycles 6a,b were alkylated, separately, with propargyl bromide to obtain, regioselectively, 4-(methyl and benzyl )thio-1-(prop-2-ynyl)-1H-pyrazolo[3,4-d]pyrimidines 7a,b. These N-1-alkylated products were condensed with compound 9 via a 1,3-dipolar cycloaddition reaction to obtain, after separation and deprotection, 1,4-and 1,5-regioisomers 12a,b and 13a,b. The deprotected acyclic nucleosides 12a and 13a served as precursors for thepreparation of 4-amino (14 and 15), 4-methylamino (16 and 17), 4-benzylamino (18 and 19), 4-methoxy (20 and 21) and 4-hydroxy (22 and 23) analogues. Compounds 7a,b and all deprotected acyclic nucleosides were evaluated for their inhibitory effects against the replication of HIV-1(IIIB) and HIV-2(ROD) in MT-4 cells and for their anti-tumor activity. No marked activity was found. However, initial evaluation of 6a,b, 7a,b, 12a,b, 13a,b and 14-23 showed that compound 7b has marked activity against M. tuberculosis.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 29/01/20 alle ore 19:13:31