Al-Masoudi, Najim A.; Al-Soud, Yaseen A.; Ehrmann, Michael; Clercq, Erik de:
Synthesis of acyclic 6,7-dihaloquinolone nucleoside analogues as potential antibacterial and antiviral agents.
2000
In: Bioorganic & medicinal chemistry : a Tetrahedron publication for the rapid dissemination of full original research papers and critical reviews on biomolecular chemistry, medicinal chemistry and related disciplines, Jg. 8 (2000), Heft 6, S. 1407 - 1413
Artikel/Aufsatz in Zeitschrift / Fach: Biologie
Titel:
Synthesis of acyclic 6,7-dihaloquinolone nucleoside analogues as potential antibacterial and antiviral agents.
Autor(in):
Al-Masoudi, Najim A.; Al-Soud, Yaseen A.; Ehrmann, Michael im Online-Personal- und -Vorlesungsverzeichnis LSF anzeigen; Clercq, Erik de
Erscheinungsjahr
2000
Erschienen in:
Bioorganic & medicinal chemistry : a Tetrahedron publication for the rapid dissemination of full original research papers and critical reviews on biomolecular chemistry, medicinal chemistry and related disciplines, Jg. 8 (2000), Heft 6, S. 1407 - 1413
ISSN
WWW URL

Abstract:

Reaction of the quinolone carboxylic acids 1 and 2 with (2-acetoxyethoxy)methyl chloride 3 in the presence of n-Bu4NI afforded the N-alkylated products 4 and 6, which could be deblocked to the free nucleoside analogues 5 and 7, respectively. The alkylated quinolone carboxylic acids 9 and 10 were obtained by condensation of 1 and 2 with 1,4-dichlorobut-2-ene 8 in the presence of NaH. Hydrolysis of 9 gave the alcohol 11. Similar treatment of 1 with 8 in the presence of K2CO3 at relatively high temperature furnished 12. Prolonged heating of the ester 13 with 8 in NaH/DMF afforded the conjugated-diene 15. Treatment of 1 and 2 with dimethyl acetylenedicarboxylate 16 furnished the pyrano[4,3-b]quinolones 17 and 18, respectively. Antibacterial and antiviral evaluations of the new products are reported.