Anthracyclines and other Glycosylated Polycyclic Antibiotics

Daunomycin has been converted into its 4 -D-phosphate and 4 -0-sulfate, and into the 3 -iV-P-D-glucuronylcarbamate, a potential substrate for P-glucuroni-dase, these compounds being prodrugs for antibody directed enzyme-prodrug therapy. The same team has also made the more complex spacer-linked 

Accounts of presentations at a symposium have described daunorubicin and doxorubicin amdogues fluorinated at C-2, and other anthracyclines with reduced basicity and increased stability of the glycosidic bond, again by introduction of halogens at C-2 The 4 -morpholino-9-methylanthracycline 21 has been synthesized, and the 3 -amino-function of carminomydn has been incorporated into a morpholine ring which also carries a hypoxanthine unit, by reductive amination with 2, 3 -seco-inosine.  

The H- and C-NMR spectra of aclacinomycin A have been fully assigned, and the results were used in a study of the solution conformation of the trisaccharide 22 of this antibiotic. The related trisaccharide 23 of ditrisarubidn B and betaclacamydn has been synthesized and its DNA-binding was studied. It was found that the DNA binding of the trisaccharide is low, indicating the need for the chromophere to anchor the antibiotic in the DNA.  

4-di-O-p-coumaroyl-a-L-rhamnopyranoside of the flavanone kaempferol, present in New Zealand Epicridaceae species, has antimicrobial activity against multi-resistant Staphylococcus aureus  

The C-ribosyl naphthoquinone exfoliamycin (24) has been isolated from Streptomyces exfoliatus, along with the products of 0-methylation and of elimination of water in ring C. The structure was determined by X-ray crystallography of a derivative the absolute configuration was not determined, but is assumed to correspond with o-ribose. The first synthesis of angucycline antibiotic Cl04 (26) has been accomplished the key intermediate 25 was made by 

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