Synthesis and antibacterial activity of pyranmycin derivatives with N-1 and O-6 modifications

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 24, 2007, Pages 7711-7719

  Li, Jie ^a   Chiang, Fang I ^a   Chen, Hsiao Nung ^a   Chang, Cheng Wei Tom ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

Aminoglycoside; Aminoglycoside resistant bacteria; Neomycin; Pyranmycin

Indexed keywords

5 O (4 AMINO 4,6 DIDEOXY BETA DEXTRO GLUCOPYRANOSYL) 6 O (2 AMINOETHYL) 1 N (4 AMINO 2 HYDROXYBUTANOYL)NEAMINE; 5 O (4 AMINO 4,6 DIDEOXY BETA DEXTRO GLUCOPYRANOSYL) 6 O (2 HYDROXYETHYL) 1 N (4 AMINO 2 HYDROXYBUTANOYL)NEAMINE; 5 O (4 AMINO 4,6 DIDEOXY BETA DEXTRO GLUCOPYRANOSYL) 6 O PROPYL 1 N (4 AMINO 2 HYDROXYBUTANOYL)NEAMINE; AMINOGLYCOSIDE ANTIBIOTIC AGENT; BUTIROSIN A; FRAMYCETIN; JT 005; JT 050; JT 051; JT 052; PYRANMYCIN; PYRANMYCIN DERIVATIVE; RIBOSTAMYCIN; TC 005; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL STRAIN; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG SYNTHESIS; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; CARBOHYDRATE SEQUENCE; DRUG RESISTANCE, BACTERIAL; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; NITROGEN; OXYGEN; STRUCTURE-ACTIVITY RELATIONSHIP;

ESCHERICHIA COLI;

EID: 35348882246     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.08.059     Document Type: Article

References (20)

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17. Various conditions were attempted. However, the poor regioselectivity and yield were achieved: (1) Using LiHMDS as the base and THF as the solvent, no reaction occurred; (2) Using LiHMDS as the base and DMF as the solvent, no mono-O-6 allylated product was obtained; (3) Using NaH as the base, no mono-O-6 allylated product was obtained.
18. The procedure was modified from Methods for Dilution Antimicrobial Susceptibility Testing for Bacteria that Grow Aerobically. Approved standard M7-A5, and Performance Standards for Antimicrobial Disk Susceptibility Tests. Approved standard M2-A7, National Committee for Clinical Laboratory Standards, Wayne, PA.
19. Molecular modeling was conducted using HyperChem 7.0 based on the X-ray structure reported by Mobashery and co-workers (Ref. 20).
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