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Media type:
E-Article
Title:
Synthesis of (3′,3′‐Dimethyloxiranyl)quinones and (Dimethylacetyl)quinones as Potential Cytostatics
Contributor:
Kloc, Krystian;
Młochowski, Jacek;
Syper, Ludwik;
Mordarski, Marian
Published:
Wiley, 1986
Published in:
Journal für Praktische Chemie, 328 (1986) 3, Seite 419-429
Language:
English
DOI:
10.1002/prac.19863280318
ISSN:
0021-8383
Origination:
Footnote:
Description:
Abstract1,4‐Benzoquinones and 1,4‐naphthoquinones carrying 3′,3′‐dimethyloxiranyl, dimethylacetyl or oxiranylmethyloxy substituents (1, 2 or 3) have been synthesized. The methods presented involved epoxidation of a sterically overcrowded double bond as a crucial step for synthesis of (3′,3′‐dimethyloxiranyl)quinones 1. Reaction of aryllithium derivatives with 2‐chloro‐2‐methyl‐propanol unexpectedly led to (dimethyl)acetylarenes 11 subsequently oxidized to (dimethylacetyl)‐quinones 2. High cytotoxicity of 1 against KB cells has been revealed contrary to significantly lower activity of 2 and 3. The structure‐activity relationship was discussed in terms of current theory of biologically activated alkylating agents.