Synthesis and biological evaluation of new fragments from kirromycin antibiotic.
New N-acyl derivatives of 1-N-desmethyl goldinamine were obtained from degradation of kirromycin. Periodate-oxidation of these derivatives provided new aldehydic fragments that were further elaborated. Both N-phenyl ureido and N-phthalimido derivatives of 1-N-desmethyl goldinamine are able to inhibit bacterial protein synthesis in cell-free assay and are active against whole microorganisms, although with lower potency than kirromycin. The derivatives from the aldehydic fragments are totally inactive.
Tavecchia
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P
Lepetit Research Center, Gerenzano (VA), Italy.
Marazzi
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A
Dallanoce
C
C
Trani
A
A
Ciciliato
I
I
Ferrari
P
P
Selva
E
E
Ciabatti
R
R
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D001426:Bacterial Proteins / Q000096:biosynthesis; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010671:Phenylurea Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010797:Phthalimides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011728:Pyridones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
C104492:1-N-desmethyl-25-N-phenylureidogoldinamine; C104493:1-N-desmethyl-25-N-phthaloylgoldinamine; D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D010671:Phenylurea Compounds; D010797:Phthalimides; D011728:Pyridones; C008536:mocimycin