Antibiotika aus Gleitenden Bakterien, L – Chemische Modifikation von Sorangicin A und Struktur‐Wirkungs‐Beziehung II: Derivate aus Reduktions‐, Oxidations‐ und Umlagerungsreaktionen

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Abstract
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.

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