DIASTEREOSELECTIVE SYNTHESIS OF OCTAHYDRO-14H-BENZO[G]QUINOLINO[2,3-A]QUINOLIDINES - IMPROVED CYTOTOXIC ACTIVITY AGAINST HUMAN BRAIN-TUMOR CELL-LINES AS A RESULT OF THE INCREASED RIGIDITY OF THE MOLECULAR BACKBONE

Authors
MONSEES A LASCHAT S HOTFILDER M JONES PG
Citation
A. Monsees et al., DIASTEREOSELECTIVE SYNTHESIS OF OCTAHYDRO-14H-BENZO[G]QUINOLINO[2,3-A]QUINOLIDINES - IMPROVED CYTOTOXIC ACTIVITY AGAINST HUMAN BRAIN-TUMOR CELL-LINES AS A RESULT OF THE INCREASED RIGIDITY OF THE MOLECULAR BACKBONE, Bioorganic & medicinal chemistry letters, 8(20), 1998, pp. 2881-2884
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
8
Issue
20
Year of publication
1998
Pages
2881 - 2884
Database
ISI
SICI code
0960-894X(1998)8:20<2881:DSOO>2.0.ZU;2-I
Abstract
Octahydro-14H-benzo[g]quinolino[2,3-a]quinolidines 6 were obtained in 6 steps from L-phenylalanine. The key step utilizes a diastereoselecti ve intramolecular EtAlCl2-catalyzed hetero-Diels-Alder reaction. Compo unds 6a-f were tested in vitro against human medulloblastoma D283 Med and glioblastoma A-172 and T98G cell lines and showed improved cytotox icity compared to the corresponding, less rigid pyrido[1,2-b]isoquinol ines 1. (C) 1998 Elsevier Science Ltd. Ail rights reserved.