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Desmethyl(trifluormethyl)actinomycine
Author(s) -
Giencke Astrid,
Lackner Helmut
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001106
Subject(s) - trifluoromethyl , chemistry , benzoic acid , desmethyl , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , metabolite , alkyl
Demethyl(trifluoromethyl)actinomycins The synthesis of new 4‐(trifluoromethyl)benzoic acid derivatives 2 – 10 and their coupling with amino acids and peptides 12, 13, 15 is described. They serve as precursors for the synthesis of the hitherto unknown demethyl(trifluoromethyl)actinocin dimethyl esters 11 , demethyl‐trifluoromethyl‐actino‐cinyl peptides 14, 16, 18 and the demethyl‐trifluoromethyl‐actinomycins 17 . Although spacially comparable with the methyl residues, the 4‐ and 6‐trifluoromethyl groups have unexpected strong influences on the antibiotic and cytostatic properties of the actinomycins. The CH 3 /CF 3 exchange makes it possible to bring NMR‐analytically useful hetero nuclei into the centre of the actinomycin/DNA complex (Figure 1).