ISSN:
0947-3440
Keywords:
Antibiotics
;
Benzoisochromanquinones
;
Isokalafungins
;
Isonanaomycins
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Structurally Modified Isokalafungins and IsonanaomycinsThe total synthesis of structural analogues of the unnatural, C-6-hydroxylated isokalafungins and isonanaomycins is described. The new compounds show improved antibiotic activity and support theories for a mechanism of action which base on the formation of reactive quinone methides. Calculations of the molecular structures show that the chromophore of the most active 9-methyl derivatives 28 and 32 is bended off along its 5-CO-10-CO axis. This corresponds to an unusual shifting of characteristic 13C-NMR signals. Different experiments for the introduction of X-CH2- or sugar residues into 1 (e.g. isolactoquinomycins) demonstrate the limits of the general synthetic pathway. Finally a short overview on significant structure/activity relationships in the (iso)nanaomycin D field is given.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199519950113
