Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus A activity relationship study using a combination of NMR spectroscopy and molecular modeling

被引：24

作者：

Kolocouris, A

Tataridis, D

Fytas, G ^{[1
]}

Mavromoustakos, T

Foscolos, GB

Kolocouris, N

De Clercq, E

机构：

[1] Univ Athens, Dept Pharm, Div Pharmaceut Chem, GR-15771 Athens, Greece

[2] Natl Hellen Res Fdn, Inst Organ & Pharmaceut Chem, GR-11635 Athens, Greece

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 24期

关键词：

D O I：

10.1016/S0960-894X(99)00631-9

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The 2-(2-adamantyl)piperidines 13 and 15a-c were synthesized and evaluated for anti-influenza virus A and B activity. The parent N-H compound 13 was 3-4 times more active than amantadine and rimantadine against H2N2 influenza A. N-alkylation of 13 resulted in derivatives 15a-c that were devoid of biological activity. This dramatic reduction in biological activity may be attributed to the different conformational properties between N-H and N-alkyl piperidines, as deduced from the combination of computational chemistry and NMR spectroscopy. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

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页码：3465 / 3470

页数：6

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