New synthetic pathway to diverse 2-substituted quinolines based on a multicomponent reaction: Solution-phase and solid-phase applications

被引：41

作者：

Demaude, T ^{[1
]}

Knerr, L ^{[1
]}

Pasau, P ^{[1
]}

机构：

[1] UCB Pharma SA, Combinatorial Chem & Automat Grp, Chem Res, Chemin Foriest, B-1420 Braine Lalleud, Belgium

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/cc049937c

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Using Kobayashi's modification of the Grieco reaction, we were able to synthesize diverse 4-phenylthio-1,2,3,4-tetrahydroquinolines. These intermediates were oxidized and subsequently pyrolized to provide the corresponding quinolines. This new approach to 2-substituted quinolines was exemplified by liquid-phase production of a 25-member library. This was extended to solid-phase chemistry, starting from (L)-4-nitrophenylalanine on Wang resin, for production of a 16-member library. The latter compounds possess potentially interesting VLA-4 antagonist properties.

引用

页码：768 / 775

页数：8

共 32 条

[1]

ATWELL GJ, 1989, J MED CHEM, V32, P393

[2] 8-methoxyquinolines as PDE4 inhibitors [J].

Billah, M ;

Buckley, GM ;

Cooper, N ;

Dyke, HJ ;

Egan, R ;

Ganguly, A ;

Gowers, L ;

Haughan, AF ;

Kendall, HJ ;

Lowe, C ;

Minnicozzi, M ;

Montana, JG ;

Oxford, J ;

Peake, JC ;

Picken, CL ;

Piwinski, JJ ;

Naylor, R ;

Sabin, V ;

Shih, NY ;

Warneck, JBH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (12) :1617-1619

[3] Synthesis and profile of SCH351591, a novel PDE4 inhibitor [J].

Billah, M ;

Cooper, N ;

Cuss, F ;

Davenport, RJ ;

Dyke, HJ ;

Egan, R ;

Ganguly, A ;

Gowers, L ;

Hannah, DR ;

Haughan, AF ;

Kendall, HJ ;

Lowe, C ;

Minnicozzi, M ;

Montana, JG ;

Naylor, R ;

Oxford, J ;

Peake, JC ;

Piwinski, JJ ;

Runcie, KA ;

Sabin, V ;

Sharpe, A ;

Shih, NY ;

Warneck, JBH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (12) :1621-1623

[4] 8-methoxyquinoline-5-carboxamides as PDE4 inhibitors: A potential treatment for asthma [J].

Buckley, GM ;

Cooper, N ;

Dyke, HJ ;

Galleway, FP ;

Gowers, L ;

Haughan, AF ;

Kendall, HJ ;

Lowe, C ;

Maxey, R ;

Montana, JG ;

Naylor, R ;

Oxford, J ;

Peake, JC ;

Picken, CL ;

Runcie, KA ;

Sabin, V ;

Sharpe, A ;

Warneck, JBH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (12) :1613-1615

[5] Development of 2,2-dimethylchromanol cysteinyl LT1 receptor antagonists [J].

Chambers, RJ ;

Antognoli, GW ;

Cheng, JB ;

Kuperman, AV ;

Liston, TC ;

Marfat, A ;

Owens, BS ;

Pillar, JS ;

Shirley, JT ;

Watson, JW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (24) :3577-3582

[6] Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines [J].

Cho, CS ;

Kim, BT ;

Choi, HJ ;

Kim, TJ ;

Shim, SC .

TETRAHEDRON, 2003, 59 (40) :7997-8002

[7]

CHRISTENSEN T, 1979, ACTA CHEM SCAND B, V33, P763, DOI 10.3891/acta.chem.scand.33b-0763

[8] Synthesis of 2-CF3-tetrahydroquinoline and quinoline derivatives from CF3-N-aryl-aldimine [J].

Crousse, B ;

Bégué, JP ;

Bonnet-Delpon, D .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :5009-5013

[9] Expeditious preparation of 2-substituted quinolines [J].

Fakhfakh, MA ;

Franck, X ;

Fournet, A ;

Hocquemiller, R ;

Figadère, B .

TETRAHEDRON LETTERS, 2001, 42 (23) :3847-3850

[10] STEREOSPECIFIC SYNTHESIS, ASSIGNMENT OF ABSOLUTE-CONFIGURATION, AND BIOLOGICAL-ACTIVITY OF THE ENANTIOMERS OF 3-[[[3-[2-(7-CHLOROQUINOLIN-2-YL)-(E)-ETHENYL]PHENYL][[3-(DIMETHYLAMINO)-3-OXOPROPYL]THIO]METHYL]THIO]PROPIONIC ACID, A POTENT AND SPECIFIC LEUKOTRIENE-D4 RECEPTOR ANTAGONIST [J].

GAUTHIER, JY ;

JONES, T ;

CHAMPION, E ;

CHARETTE, L ;

DEHAVEN, R ;

FORDHUTCHINSON, AW ;

HOOGSTEEN, K ;

LORD, A ;

MASSON, P ;

PIECHUTA, H ;

PONG, SS ;

SPRINGER, JP ;

THERIEN, M ;

ZAMBONI, R ;

YOUNG, RN .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2841-2845

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