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Synthesis and preliminary cytotoxic activity of dimethoxy‐acridines and dimethoxynitroacridines
Author(s) -
Monge A.,
MartínezCrespo F. J.,
Santamaría L.,
Narro S.,
De Ceráin A. López,
Hamilton E.,
Barker A. J.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310628
Subject(s) - nitration , chemistry , acridine , phenol , condensation , anthranilic acid , organic chemistry , nitro , ullmann reaction , medicinal chemistry , catalysis , alkyl , physics , thermodynamics
The preparation of a series of dimethoxy and dimethoxynitroacridines and their activity in oxic and hypoxic cells is reported. Anthranilic acids 1,4,14 were prepared according to the Ullmann condensation. 9‐chloroacridines were obtained from anthranilic acids by refluxing in phosphorus oxychloride. The synthesis of two new acridine dimers 9,10 is described. Nitration of 9‐chloro‐2,4‐dimethoxyacridine 15 gave 3‐nitro isomer 19 . By phenol‐mediated coupling reaction from all the 9‐chloroacridines, the respective 9‐(alkylamino)acridines were obtained. By nitration of 17 a new 2,4‐dimethoxy‐3,7‐dinitroacridine 21 was prepared