salicylates and saphenamycin

salicylates has been researched along with saphenamycin* in 2 studies

Other Studies

2 other study(ies) available for salicylates and saphenamycin

Article	Year
First synthesis of racemic saphenamycin and its enantiomers. investigation of biological activity. Bioorganic & medicinal chemistry, 2003, Mar-06, Volume: 11, Issue:5 The natural antibiotic saphenamycin, 6-[1-(2-hydroxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid, was synthesized from saphenic acid using temporary allyl protection of carboxy and phenoxy functionalities. Resolution of racemic saphenic acid was performed by crystallization of the corresponding (-)-brucine diastereomeric salts and the absolute configuration of (-)-brucinium (-)-saphenate was determined by X-ray crystallography to have R-configuration. This also proved to be the configuration of natural saphenic acid. Enantiomers of saphenamycin were obtained from resolved saphenic acid and screened against a range of skin flora and resistant Staphylococcus aureus strains. Biological activities of saphenamycin enantiomers were compared with that of the synthetic racemate as well as earlier reported activities of saphenamycin isolated from natural sources. No significant difference was observed in activity of the enantiomers of saphenamycin, which revealed that the chirality of saphenamycin has no consequences for the antibiotic activity. Saphenamycin proved to be a potent antibiotic against fusidic acid and rifampicin resistant S. aureus strains showing MIC of 0.1-0.2 microg/mL. Topics: Anti-Bacterial Agents; Bacteria; Chemical Phenomena; Chemistry, Physical; Crystallography, X-Ray; Indicators and Reagents; Magnetic Resonance Spectroscopy; Mass Spectrometry; Microbial Sensitivity Tests; Models, Molecular; Phenazines; Salicylates; Stereoisomerism	2003
Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors. Organic & biomolecular chemistry, 2003, Sep-21, Volume: 1, Issue:18 Inspired by the occurrence and function of phenazines in natural products, new glycosylated analogs were designed and synthesized. DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors were used in an efficient and easily-handled glycosylation protocol compatible with combinatorial chemistry. Benzoylated D-glucose, D-galactose and L-quinovose DISAL glycosyl donors were synthesized in high yields and used under mild conditions to glycosylate methyl saphenate and 2-hydroxyphenazine. The glycosides were screened for biological activity and one compound showed inhibitory activity towards topoisomerase II. Topics: Chemistry, Organic; Chromatography, High Pressure Liquid; Glycosylation; Models, Chemical; Phenazines; Salicylates; Streptomyces	2003

Article

Year

First synthesis of racemic saphenamycin and its enantiomers. investigation of biological activity.

Bioorganic & medicinal chemistry, 2003, Mar-06, Volume: 11, Issue:5

The natural antibiotic saphenamycin, 6-[1-(2-hydroxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid, was synthesized from saphenic acid using temporary allyl protection of carboxy and phenoxy functionalities. Resolution of racemic saphenic acid was performed by crystallization of the corresponding (-)-brucine diastereomeric salts and the absolute configuration of (-)-brucinium (-)-saphenate was determined by X-ray crystallography to have R-configuration. This also proved to be the configuration of natural saphenic acid. Enantiomers of saphenamycin were obtained from resolved saphenic acid and screened against a range of skin flora and resistant Staphylococcus aureus strains. Biological activities of saphenamycin enantiomers were compared with that of the synthetic racemate as well as earlier reported activities of saphenamycin isolated from natural sources. No significant difference was observed in activity of the enantiomers of saphenamycin, which revealed that the chirality of saphenamycin has no consequences for the antibiotic activity. Saphenamycin proved to be a potent antibiotic against fusidic acid and rifampicin resistant S. aureus strains showing MIC of 0.1-0.2 microg/mL.

Topics: Anti-Bacterial Agents; Bacteria; Chemical Phenomena; Chemistry, Physical; Crystallography, X-Ray; Indicators and Reagents; Magnetic Resonance Spectroscopy; Mass Spectrometry; Microbial Sensitivity Tests; Models, Molecular; Phenazines; Salicylates; Stereoisomerism

2003

Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors.

Organic & biomolecular chemistry, 2003, Sep-21, Volume: 1, Issue:18

Inspired by the occurrence and function of phenazines in natural products, new glycosylated analogs were designed and synthesized. DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors were used in an efficient and easily-handled glycosylation protocol compatible with combinatorial chemistry. Benzoylated D-glucose, D-galactose and L-quinovose DISAL glycosyl donors were synthesized in high yields and used under mild conditions to glycosylate methyl saphenate and 2-hydroxyphenazine. The glycosides were screened for biological activity and one compound showed inhibitory activity towards topoisomerase II.

Topics: Chemistry, Organic; Chromatography, High Pressure Liquid; Glycosylation; Models, Chemical; Phenazines; Salicylates; Streptomyces

2003