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Titolo:
Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and1,2,4-triazolo[3,4-b][1,3,4]thiadiazine
Autore:
El Ashry, EH; Awad, LF;
Indirizzi:
Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt Univ Alexandria Alexandria Egypt Fac Sci, Dept Chem, Alexandria, Egypt
Titolo Testata:
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
fascicolo: 1-2, volume: 20, anno: 2001,
pagine: 103 - 116
SICI:
1525-7770(2001)20:1-2<103:NSOSTO>2.0.ZU;2-M
Fonte:
ISI
Lingua:
ENG
Soggetto:
SPECTRUM ANTIVIRAL ACTIVITY; MAGNETIC-RESONANCE SPECTRA; CONFORMATIONAL-ANALYSIS; DEUTERIUM-OXIDE; 1-(CHLOROALKYL)-1-AZA-2-AZONIAALLENE SALTS; HETEROCYCLIC-SYSTEMS; ANTIFUNGAL ACTIVITY; C-13 NMR; DERIVATIVES; ANALOGS;
Keywords:
seco C-nucleosides; 1,2,4-triazoles; 1,2,4-triazolo[3,4-b][1,3,4] thiadiazines;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
59
Recensione:
Indirizzi per estratti:
Indirizzo: El Ashry, EH Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt Univ Alexandria Alexandria Egypt t Chem, Alexandria, Egypt
Citazione:
E.H. El Ashry e L.F. Awad, "Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and1,2,4-triazolo[3,4-b][1,3,4]thiadiazine", NUCLEOS NUC, 20(1-2), 2001, pp. 103-116

Abstract

The seco C-nucleosides 3-(1,2,3,4,5-penta-O-acetyl-D-gluco- and D-galacto-pentitol-1-yl)-1H-1,2,4-triazole (8 and 9) were obtained in a one pot by deamination and dethiolation of 4-amino-3-(D-gluco- and D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazoles (1 and 2), respectively, using sodium nitrite in orthophosphoric acid and subsequent acetylation. Condensation of 1, 2,and 4-amino-3-(D-glycero-D-gulo-hexitol-1-yl)-5-mercapto-1,2,4-triazole (12) with phenacylbromide (11) afforded the corresponding 3-(D-gluco-, D-galactopentitol-1-yl)) and 3-(D-glycero-D-gulo-hexitol-1-yl)-6-phenyl-7H-1,2,4-,2,4-triazolo[3,4-b] [1,3,4] thiadiazines (15, 16, and 17). Acetylation of 15-17 gave the penta- and hexa-O-acetyl derivatives 18-20, respectively. The structures were confirmed by using H-1,C-13, and 2D NMR spectra, DQFCQSY,HMQC, and HMBC experiments. The favored conformational structures were deduced from the vicinal coupling constants of the protons.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 20/01/20 alle ore 07:37:32