Synthesis and structure-activity relationship of 4-quinolone-3-carboxylic acid based inhibitors of glycogen synthase kinase-3β

被引：20

作者：

Cociorva, Oana M. ^{[1
]}

Li, Bei ^{[1
]}

Nomanbhoy, Tyzoon ^{[1
]}

Li, Qiang ^{[1
]}

Nakamura, Ayako ^{[2
]}

Nakamura, Kai ^{[1
]}

Nomura, Masahiro ^{[2
]}

Okada, Kyoko ^{[2
]}

Seto, Shigeki ^{[2
]}

Yumoto, Kazuhiro ^{[2
]}

Liyanage, Marek ^{[1
]}

Zhang, Melissa C. ^{[1
]}

Aban, Arwin ^{[1
]}

Leen, Brandon ^{[1
]}

Szardenings, Anna Katrin ^{[1
]}

Rosenblum, Jonathan S. ^{[1
]}

Kozarich, John W. ^{[1
]}

Kohno, Yasushi ^{[2
]}

Shreder, Kevin R. ^{[1
]}

机构：

[1] ActivX Biosci Inc, La Jolla, CA 92037 USA

[2] Kyorin Pharmaceut Co Ltd, Discovery Res Labs, Nogi, Tochigi, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 19期

关键词：

GSK-3 beta inhibitor; 4-Quinolone; 3-Carboxylic acid; Anti-bacterial; Kinase profiling;

D O I：

10.1016/j.bmcl.2011.07.073

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis, GSK-3 beta inhibitory activity, and anti-microbial activity of bicyclic and tricyclic derivatives of the 5,7-diamino-6-fluoro-4-quinolone-3-carboxylic acid scaffold were studied. Kinase selectivity profiling indicated that members of this class were potent and highly selective GSK-3 inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5948 / 5951

页数：4

共 11 条

[1] Glycogen synthase kinase 3: a drug target for CNS therapies [J].

Bhat, RV ;

Haeberlein, SLB ;

Avila, J .

JOURNAL OF NEUROCHEMISTRY, 2004, 89 (06) :1313-1317

[2] FLUORONAPHTHYRIDINES AS ANTIBACTERIAL AGENTS .4. SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF 5-SUBSTITUTED-6-FLUORO-7-(CYCLOALKYLAMINO)-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACIDS [J].

BOUZARD, D ;

DICESARE, P ;

ESSIZ, M ;

JACQUET, JP ;

LEDOUSSAL, B ;

REMUZON, P ;

KESSLER, RE ;

FUNGTOMC, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (03) :518-525

[3] Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription [J].

Coghlan, MP ;

Culbert, AA ;

Cross, DAE ;

Corcoran, SL ;

Yates, JW ;

Pearce, NJ ;

Rausch, OL ;

Murphy, GJ ;

Carter, PS ;

Cox, LR ;

Mills, D ;

Brown, MJ ;

Haigh, D ;

Ward, RW ;

Smith, DG ;

Murray, KJ ;

Reith, AD ;

Holder, JC .

CHEMISTRY & BIOLOGY, 2000, 7 (10) :793-803

[4]

De Sarro A, 2001, CURR MED CHEM, V8, P371

[5] Recent Advances in the Discovery of GSK-3 Inhibitors and a Perspective on their Utility for the Treatment of Alzheimer's Disease [J].

Gentles, Robert G. ;

Hu, Shuanghua ;

Dubowchik, Gene M. .

ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 44, 2009, 44 :3-+

[6] Glycogen synthase kinase-3β is a negative regulator of cardiomyocyte hypertrophy [J].

Haq, S ;

Choukroun, G ;

Kang, ZB ;

Ranu, H ;

Matsui, T ;

Rosenzweig, A ;

Molkentin, JD ;

Alessandrini, A ;

Woodgett, J ;

Hajjar, R ;

Michael, A ;

Force, T .

JOURNAL OF CELL BIOLOGY, 2000, 151 (01) :117-129

[7] GSK3, a master switch regulating cell-fate specification and tumorigenesis [J].

Kim, L ;

Kimmel, AR .

CURRENT OPINION IN GENETICS & DEVELOPMENT, 2000, 10 (05) :508-514

[8] SYNTHESIS OF NOVEL 5-FLUORO ANALOGS OF NORFLOXACIN AND CIPROFLOXACIN [J].

MORAN, DB ;

ZIEGLER, CB ;

DUNNE, TS ;

KUCK, NA ;

LIN, YI .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1313-1318

[9] Functional interrogation of the kinome using nucleotide acyl phosphates [J].

Patricelli, Matthew P. ;

Szardenings, A. Katrin ;

Liyanage, Marek ;

Nomanbhoy, Tyzoon K. ;

Wu, Min ;

Weissig, Helge ;

Aban, Arwin ;

Chun, Doris ;

Tanner, Stephen ;

Kozarich, John W. .

BIOCHEMISTRY, 2007, 46 (02) :350-358

[10] In Situ Kinase Profiling Reveals Functionally Relevant Properties of Native Kinases [J].

Patricelli, Matthew P. ;

Nomanbhoy, Tyzoon K. ;

Wu, Jiangyue ;

Brown, Heidi ;

Zhou, David ;

Zhang, Jianming ;

Jagannathan, Subadhra ;

Aban, Arwin ;

Okerberg, Eric ;

Herring, Chris ;

Nordin, Brian ;

Weissig, Helge ;

Yang, Qingkai ;

Lee, Jiing-Dwan ;

Gray, Nathanael S. ;

Kozarich, John W. .

CHEMISTRY & BIOLOGY, 2011, 18 (06) :699-710

← 1 2 →