Monastrol analogs: A synthesis of pyrazolopyridine, benzopyranopyrazolopyridine, and oxygen-bridged azolopyrimidine derivatives and their biological screening

被引：38

作者：

Svetlik, Jan ^{[1
]}

Veizerova, Lucia ^{[1
]}

Mayer, Thomas U. ^{[2
]}

Catarinella, Mario ^{[2
]}

机构：

[1] Comenius Univ, Dept Pharmaceut Anal & Nucl Pharm, SK-83232 Bratislava, Slovakia

[2] Univ Konstanz, Dept Mol Genet, D-78457 Constance, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 14期

关键词：

Biginelli reaction; Hantzsch reaction; Oxygen-bridged nitrogen heterocycles; Monastrol analogs; INHIBITORS; EG5; IDENTIFICATION; HETEROCYCLES; POTENT;

D O I：

10.1016/j.bmcl.2010.05.085

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A synthesis of novel pyrazolopyridine, benzopyranopyrazolopyridine, and oxygen-bridged pyrazolo-, tetrazolo, benzimidazo-, and thiazolopyrimidines via Hantzsch- and Biginelli-like condensations has been developed. The ability of these compounds to inhibit Eg5 activity has been examined. The results indicate that synthetic manipulations in the monastrol thiourea moiety are inefficient. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4073 / 4076

页数：4

共 33 条

[1]

BARTASHEVICH EV, 1999, IZV AN K, P1573

[2] Lack of efficacy of melanin-concentrating hormone-1 receptor antagonists in models of depression and anxiety [J].

Basso, Ana M. ;

Bratcher, Natalie A. ;

Gallagher, Kelly B. ;

Cowart, Marlon D. ;

Zhao, Chen ;

Sun, Minghua ;

Esbenshade, Timothy A. ;

Brune, Michael E. ;

Fox, Gerard B. ;

Schmidt, Martin ;

Collins, Christine A. ;

SouerS, Andrew J. ;

Iyengar, Rajesh ;

Vasudevan, Anil ;

Kyrn, Philip R. ;

Hancock, Arthur A. ;

Rueter, Lynne E. .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2006, 540 (1-3) :115-120

[3]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[4] Identification and characterization of 4-aryl-3,4-dihydropyrimidin2(1H)-ones as inhibitors of the fatty acid transporter FATP4 [J].

Blackburn, C ;

Guan, B ;

Brown, J ;

Cullis, C ;

Condon, SM ;

Jenkins, TJ ;

Peluso, S ;

Ye, YC ;

Gimeno, RE ;

Punreddy, S ;

Sun, Y ;

Wu, H ;

Hubbard, B ;

Kaushik, V ;

Tummino, P ;

Sanchetti, P ;

Sun, DY ;

Daniels, T ;

Tozzo, E ;

Balani, SK ;

Raman, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (13) :3504-3509

[5] N-POLYLAZOLYLMETHANES .3. SYNTHESIS AND PROTON MAGNETIC-RESONANCE OF 1,1'-METHYLENEDIIMIDAZOLE AND OF 1,1'-METHYLENEDIBENZIMIDAZOLE DERIVATIVES [J].

CLARAMUNT, RM ;

ELGUERO, J ;

MECO, T .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (05) :1245-1249

[6] Kinesin spindle protein (KSP) inhibitors.: Part V:: Discovery of 2-propylamino-2,4-diaryl-2,5-dihydropyrroles as potent, water-soluble KSP inhibitors, and modulation of their basicity by β-fluorination to overcome cellular efflux by P-glycoprotein [J].

Cox, Christopher D. ;

Breslin, Michael J. ;

Whitman, David B. ;

Coleman, Paul J. ;

Garbaccio, Robert M. ;

Fraley, Mark E. ;

Zrada, Matthew M. ;

Buser, Carolyn A. ;

Walsh, Eileen S. ;

Hamilton, Kelly ;

Lobell, Robert B. ;

Tao, Weikang ;

Abrams, Marc T. ;

South, Vicki J. ;

Huber, Hans E. ;

Kohl, Nancy E. ;

Hartman, George D. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (10) :2697-2702

[7] Structure-activity relationship of S-trityl-L-cysteine analogues as inhibitors of the human mitotic kinesin Eg5 [J].

DeBonis, Salvatore ;

Skoufias, Dimitrios A. ;

Indorato, Rose-Laure ;

Liger, Francois ;

Marquet, Bernard ;

Laggner, Christian ;

Joseph, Benoit ;

Kozielski, Frank .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (05) :1115-1125

[8] Inhibition of hepatitis B virus replication by drug-induced depletion of nucleocapsids [J].

Deres, K ;

Schröder, CH ;

Paessens, A ;

Goldmann, S ;

Hacker, HJ ;

Weber, O ;

Krämer, T ;

Niewöhner, U ;

Pleiss, U ;

Stoltefuss, J ;

Graef, E ;

Koletzki, D ;

Masantschek, RNA ;

Reimann, A ;

Jaeger, R ;

Gross, R ;

Beckermann, B ;

Schlemmer, KH ;

Haebich, D ;

Rübsamen-Waigmann, H .

SCIENCE, 2003, 299 (5608) :893-896

[9] Development and biological evaluation of potent and specific inhibitors of mitotic kinesin eg5 [J].

Gartner, M ;

Sunder-Plassmann, N ;

Seiler, J ;

Utz, M ;

Vernos, I ;

Surrey, T ;

Giannis, A .

CHEMBIOCHEM, 2005, 6 (07) :1173-+

[10] Biologically active dihydropyrimidones of the Biginelli-type - a literature survey [J].

Kappe, CO .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (12) :1043-1052

← 1 2 3 4 →