A Three-Component Reaction Forming Naphthyridones - Synthesis of Lophocladine Analogs

被引：13

作者：

Sellstedt, Magnus ^{[1
]}

Almqvist, Fredrik ^{[1
]}

机构：

[1] Umea Univ, Dept Chem, SE-90187 Umea, Sweden

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 19期

关键词：

MULTICOMPONENT REACTIONS; ESCHERICHIA-COLI; NATURAL-PRODUCTS; BIOGENESIS; ALKALOIDS; CYCLIZATION; INHIBITORS;

D O I：

10.1021/ol202080x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-component reaction forming dihydro 2,7-naphthyridine-1-ones has been developed. These unstable dihydro intermediates can be either oxidized or reduced to form naphthyridones or tetrahydro naphthyridones, respectively. The reaction tolerates a large variety of aldehydes and amines, and the produced compounds are analogs of the natural product lophocladine A.

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收藏

页码：5278 / 5281

页数：4

相关论文

共 16 条

[1] Pilicides -: small molecules targeting bacterial virulence [J].

Aberg, Veronica ;

Almqvist, Fredrik .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (12) :1827-1834

[2] NOVEL NAPHTHYRIDINONE SYNTHESIS VIA ENAMINE CYCLIZATION [J].

BALDWIN, JJ ;

MENSLER, K ;

PONTICELLO, GS .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (25) :4878-4880

[3] 3,4-DIHYDRO-2-PHENYL-2H-PYRANO[2,3-B]PYRIDINES WITH POTENT ANTIRHINOVIRUS ACTIVITY [J].

BARGAR, TM ;

DULWORTH, JK ;

KENNY, MT ;

MASSAD, R ;

DANIEL, JK ;

WILSON, T ;

SARGENT, RN .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (09) :1590-1595

[4] Small-molecule inhibitors target Escherichia coli amyloid biogenesis and biofilm formation [J].

Cegelski, Lynette ;

Pinkner, Jerome S. ;

Hammer, Neal D. ;

Cusumano, Corinne K. ;

Hung, Chia S. ;

Chorell, Erik ;

Aberg, Veronica ;

Walker, Jennifer N. ;

Seed, Patrick C. ;

Almqvist, Fredrik ;

Chapman, Matthew R. ;

Hultgren, Scott J. .

NATURE CHEMICAL BIOLOGY, 2009, 5 (12) :913-919

[5] EVALUATION OF THE SIDE ARM OF (NAPHTHYLVINYL)PYRIDINIUM INHIBITORS OF CHOLINE-ACETYLTRANSFERASE [J].

DEBERNARDIS, JF ;

GIFFORD, P ;

RIZK, M ;

ERTEL, R ;

ABRAHAM, DJ ;

SIUDA, JF .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) :117-121

[6] Lophocladines, bioactive alkaloids from the red alga Lophocladia sp. [J].

Gross, H ;

Goeger, DE ;

Hills, P ;

Mooberry, SL ;

Ballantine, DL ;

Murray, TF ;

Valeriote, FA ;

Gerwick, WH .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (04) :640-644

[7] In situ generation of palladium nanoparticles: A simple and highly active protocol for oxygen-promoted ligand-free suzuki coupling reaction of aryl chlorides [J].

Han, Wei ;

Liu, Chun ;

Jin, Zi-Lin .

ORGANIC LETTERS, 2007, 9 (20) :4005-4007

[8] Multi-component reactions : Emerging chemistry in drug discovery 'From xylocain to crixivan' [J].

Hulme, C ;

Gore, V .

CURRENT MEDICINAL CHEMISTRY, 2003, 10 (01) :51-80

[9] First total synthesis of the 2,7-naphthyridine alkaloids lophocladine A and B [J].

Lotter, Matthias ;

Schilling, Johannes ;

Reimann, Eberhard ;

Bracher, Franz .

ARCHIV DER PHARMAZIE, 2006, 339 (12) :677-679

[10] Natural products as sources of new drugs over the last 25 years [J].

Newman, David J. ;

Cragg, Gordon M. .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (03) :461-477