ISSN:
0170-2041
Keywords:
Antibiotics
;
Sorangicins
;
Macrolide-polyether antibiotics
;
Structure-activity relationship
;
Enzymes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Antibiotics from Gliding Bacteria, L. - Chemical Modification of Sorangicin A and Structure-Activity Relationship II: Derivatives Obtained by Reduction, Oxidation and Rearrangement ReactionsThe synthesis of 38 derivatives of sorangicin A (1) with modifications of the three hydroxyl groups and the conjugated triene is described. By oxidation and reduction reactions 21-desoxy-21-oxo sorangicin (8), 21-epi-sorangicin (9) and 21-desoxysorangicins 14, 15 were obtained. With protection of the 21,22-diol the 24,25-didehydro-25-desoxysorangicin (18), 25-desoxy-25-oxosorangicins 21, 22 and 25-epi-sorangicins 23, 24 were prepared. Further, the 25-oxo derivatives 21, 22 were transformed into the oximes 25-28 and the 25-desoxy-25,25-difluoro sorangicin (31). Catalytic reduction of sorangicin A (1) gave the 37,43-dihydro derivative 35, thermolysis the cyclohexadienes 36, 37 and fluoride-induced isomerisation the 36,38,40-trienol ethers 38, 39. - Activities against Staphylococcus aureus, Escherichia coli, and in vitro inhibition of RNA polymerase of selected derivatives were examined. With most compounds a reduced biological activity was observed, some derivatives retained their activity (23-28, 31) and three were improved for certain strains (18, 21, 22) although they showed reduced enzyme inhibition activity.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930150
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