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Studies on quinones. Part 47. Synthesis of novel phenylaminophenanthridinequinones as potential antitumor agents.
- Source :
-
European journal of medicinal chemistry [Eur J Med Chem] 2011 Aug; Vol. 46 (8), pp. 3398-409. Date of Electronic Publication: 2011 May 12. - Publication Year :
- 2011
-
Abstract
- In our search for potential anticancer agents, a series of 8- and 9-phenylamino-3,4-tetrahydro-phenanthridine-1,7,10(2H)-triones with substituent variations at 6-, 8- and 9-positions were prepared using a highly efficient sequence involving: a) solar photoacylation reactions of benzoquinone with arylaldehydes, b) one-pot procedure for the synthesis of 3,4-dihydrophenanthridine-1,7,10(2H)-trione intermediates from acylhydroquinones and c) highly regiocontrolled acid-induced amination reaction of phenanthridinequinones with phenylamines. The members of this series were in vitro evaluated using the MTT colorimetric method against one normal cell line and three human cancer cell lines. The SAR analysis indicates that the location of nitrogen substituents on the quinone nucleus, the presence of methyl, phenyl, furyl and thienyl groups at the 6-position and the aromatization of the angular cycloaliphatic ring of the phenylamino-3,4-tetrahydrophenanthridine-1,7,10(2H)-trione pharmacophore play key roles in the antitumor activity.<br /> (Copyright © 2011 Elsevier Masson SAS. All rights reserved.)
- Subjects :
- Antineoplastic Agents pharmacology
Cell Line, Tumor
Drug Screening Assays, Antitumor
Fibroblasts cytology
Humans
Inhibitory Concentration 50
Lung Neoplasms drug therapy
Lung Neoplasms pathology
Molecular Structure
Quinones pharmacology
Stomach Neoplasms drug therapy
Stomach Neoplasms pathology
Structure-Activity Relationship
Urinary Bladder Neoplasms drug therapy
Urinary Bladder Neoplasms pathology
Aniline Compounds chemistry
Antineoplastic Agents chemical synthesis
Cell Survival drug effects
Fibroblasts drug effects
Phenanthridines chemistry
Quinones chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1768-3254
- Volume :
- 46
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- European journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 21621882
- Full Text :
- https://doi.org/10.1016/j.ejmech.2011.05.003