Matrix compare analysis discriminates subtle structural differences in a family of novel antiproliferative agents, diaryl-3-hydroxy-2,3,3a,10a-tetrahydrobenzo[ b]cycylopenta[ e]azepine-4,10(1 H,5 H)-diones

A diastereoselective synthesis of diaryl-3-hydroxy-2,3,3a,10a-tetrahydrobenzo[ b]cycylopenta[ e]azepine-4,10(1 H,5 H)-diones is described employing a tandem Michael-aldol addition as key step. The novel compounds exhibit antiproliferative activity in a panel of in vitro cultivated cancer cell lines....

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2006-04, Vol.16 (8), p.2148-2153
Hauptverfasser:	Kunick, Conrad, Bleeker, Carola, Prühs, Christian, Totzke, Frank, Schächtele, Christoph, Kubbutat, Michael H.G., Link, Andreas
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Anticancer agents Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Benzazepines - chemical synthesis Benzazepines - pharmacology Biological and medical sciences Compare analysis Cyclopentanes - chemical synthesis Cyclopentanes - pharmacology Drug Screening Assays, Antitumor General aspects Medical sciences Mice Pharmacology. Drug treatments Structure-Activity Relationship Tandem Michael-aldol cyclization Tumor Cells, Cultured
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Zusammenfassung:	A diastereoselective synthesis of diaryl-3-hydroxy-2,3,3a,10a-tetrahydrobenzo[ b]cycylopenta[ e]azepine-4,10(1 H,5 H)-diones is described employing a tandem Michael-aldol addition as key step. The novel compounds exhibit antiproliferative activity in a panel of in vitro cultivated cancer cell lines. The bioinformatic tool COMPARE was able to discriminate between two closely related subgroups of the title compounds, namely 1,3- and 2,3-disubstituted derivatives.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2006.01.071