Synthesis of acyclic 6,7-dihaloquinolone nucleoside analogues as potential antibacterial and antiviral agents

被引：14

作者：

Al-Masoudi, NA

Al-Soud, YA

Eherman, M

De Clercq, E

机构：

[1] Univ Konstanz, Fac Chem, D-78434 Constance, Germany

[2] Univ Al Al Bayt, Dept Chem, Al Mafraq, Jordan

[3] Univ Konstanz, Fac Biol, D-78434 Constance, Germany

[4] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2000年 / 8卷 / 06期

关键词：

D O I：

10.1016/S0968-0896(00)00067-5

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

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. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1407 / 1413

页数：7

共 41 条

[1]

1H- and 13C-NMR study of some 6,7-dihaloquinolone nucleosides and their derivatives [J].