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N ‐ and O ‐Methyl Derivatives of 2,3,5,10‐Tetrahydrobenzo[ g ]isoquinoline‐3,5,10‐triones
Author(s) -
Bouammali Boufelja,
Pautet Félix,
Nascimento Silène Carneiro Do,
Boitard Michèle,
Fillion Houda
Publication year - 1993
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19933260910
Subject(s) - ethylamine , isoquinoline , triethylamine , chemistry , regioselectivity , methylation , in vitro , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , catalysis , gene
Some 2,3,5,10‐tetrahydrobenzo[g]isoquinoline‐3,5,10‐triones 2 were prepared by a Diels‐Alder reaction between different 2‐azadienes 1 and 1,4‐naphthoquinone. The corresponding N ‐ and O ‐methyl derivatives 3 and 4 respectively were obtained by the use of CH 3 I in a basic medium: triethylamine (method A ), K 2 CO 3 and tris[2‐(2‐methoxyethoxy)ethylamine] (method B ) or in the presence of Ag 2 O. The reaction of N ‐methylation was regiospecific, while the O ‐methylation was regioselective. ‐ The in vitro cytotoxic activity of the prepared compounds was evaluated against murine L 1210 leukemia cells and a human tumor cell line MDA‐MB 231. A weak, not significant activity was observed (IC 50 values are ranging from 6 to > 10 μg/ml).