Synthesis and anti-influenza virus activity of tricyclic compounds with a unique amine moiety

被引：8

作者：

Oka, M ^{[1
]}

Ishiwata, Y ^{[1
]}

Iwata, N ^{[1
]}

Honda, N ^{[1
]}

Kakigami, T ^{[1
]}

机构：

[1] Kagaku Kenkyusho Co Ltd, Cent Res Lab, Hokusei Cho, Mie 5110406, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2001年 / 49卷 / 04期

关键词：

anti-influenza virus agent; 1-azabicyclo[3.3.0]octane; triperiden; adamantane;

D O I：

10.1248/cpb.49.379

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Several novel tricyclic compounds with a unique amine moiety (1, 2a-i) were designed and prepared based on the structure of triperiden for the development of anti-influenza virus agents, An in vitro antiviral assay showed that 1-(1-azabicyclo[3.3.0]octan-5-yl)-1-(4-fluorophenyl)-1-(2-tricyclo[3.3.1.1(3,7)] decyl)methan-1-ol hydrochloride (2f) has a potent anti-influenza A virus activity, Furthermore, since 2f was well tolerated in mice, 2f is promising as a novel anti-influenza virus agent for humans.

引用

页码：379 / 383

页数：5

共 16 条

[1] ANTIVIRAL ACTIVITY OF 1-ADAMANTANAMINE ( AMANTADINE ) [J].

DAVIES, WL ;

HOFFMANN, CE ;

PAULSHOCK, M ;

WOOD, TR ;

HAFF, RF ;

GRUNERT, RR ;

WATTS, JC ;

HERMANN, EC ;

NEUMAYER, EM ;

MCGAHEN, JW .

SCIENCE, 1964, 144 (362) :862-&

[2] STUDIES IN ORGANIC SULFUR COMPOUNDS .10. THE SCOPE OF THE RANEY NICKEL DESULFURIZATION OF CYCLIC HEMITHIOKETALS (1,3-OXATHIOLANES AND 1,3-OXATHIANES) [J].

DJERASSI, C ;

SHAMMA, M ;

KAN, TY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (17) :4723-4732

[3] HEMAGGLUTININ OF INFLUENZA-A VIRUS IS A TARGET FOR THE ANTIVIRAL EFFECT OF NORAKIN [J].

GHENDON, Y ;

MARKUSHIN, S ;

HEIDER, H ;

MELNIKOV, S ;

LOTTE, V .

JOURNAL OF GENERAL VIROLOGY, 1986, 67 :1115-1122

[4]

JONES RG, 1951, ORG REACTIONS, V6, P339

[5]

Kakigami T, 1998, CHEM PHARM BULL, V46, P1039

[6] Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: Design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity [J].

Kim, CU ;

Lew, W ;

Williams, MA ;

Liu, HT ;

Zhang, LJ ;

Swaminathan, S ;

Bischofberger, N ;

Chen, MS ;

Mendel, DB ;

Tai, CY ;

Laver, WG ;

Stevens, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (04) :681-690

[7]

LUECHE L, 1977, Patent No. 124521

[8] SYNTHESIS OF 7A-SUBSTITUTED BENZOYLAMINOALKYL-HEXAHYDRO-1H-PYRROLIZINES AND EVALUATION OF THEIR ANTIARRHYTHMIC ACTIVITY [J].

MIYANO, S ;

SHIMA, K ;

HAYASHIMATSU, M ;

SATOH, F ;

SUMOTO, K .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1987, 76 (05) :416-418

[9] HIGH-YIELD DIRECT SYNTHESIS OF A NEW CLASS OF TERTIARY ORGANO-LITHIUM DERIVATIVES OF POLYCYCLIC-HYDROCARBONS [J].

MOLLE, G ;

BAUER, P ;

DUBOIS, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) :2975-2981

[10]

Oka M, 1997, HETEROCYCLES, V45, P1447

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