Derivatives of tetrodecamycin.
The derivatives of tetrodecamycin (1), being introduced acyl, carbamoyl and alkyl groups at 14-hydroxyl group and modified at exo-methylene group, were synthesized and evaluated on their antibacterial activities. Although 14-O-substituted tetrodecamycins (3 approximately 19) showed weak activity against Pasteurella piscicida, they were more active against Gram-positive bacteria than 1. Among them, 15 showed approximately 10-fold higher activity than 1. The derivatives (20 approximately 23) modified at 4 or 5 positions had moderate antibacterial activity. The absolute structure of 4(R),5-dibromotetrodecamycin (23) was determined by X-ray crystallographic analysis.
Tsuchida
T
T
Institute of Microbial Chemistry, Tokyo, Japan.
Iinuma
H
H
Nakamura
K T
KT
Nakamura
H
H
Sawa
T
T
Hamada
M
M
Takeuchi
T
T
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003460:Crystallization; D018360:Crystallography, X-Ray; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010325:Pasteurella / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
C097848:4,5-dibromotetrodecamycin; C097847:4-(2-hydroxyethylthio)-5-hydrotetrodecamycin; C097844:5-(2-acetamidoethylthio)-4-hydrotetrodecamycin; D000900:Anti-Bacterial Agents; D005663:Furans; C087129:tetrodecamycin