Transformation of streptonigrin into streptonigrone; synthesis and biological evaluation of antibiotics streptonigrin and streptonigrone alkyl ethers.
A method of synthesis of antibiotic streptonigrin 8'-O-alkyl ethers by alkylation of streptonigrin diphenylmethyl ester and consequent deprotection of carboxylic group with CF3COOH is developed. An attempt to deblock carboxylic group of 8'-O-methylstreptonigrin diphenylmethyl ester by hydrogenation over Pd produced 8'-O-methylstreptonigrone. Similarly streptonigrin was transformed into streptonigrone over Pd-black in H2 stream. Methylation of streptonigrone afforded 5',5'-N-dimethyl-2',8'-O-dimethylstreptonigrone and 1',5',5'-tri-N-trimethyl-8'-O-methylstreptonigrone. Alkyl streptonigrin ethers demonstrated lower antibacterial activity in vitro than the parent antibiotic.
Preobrazhenskaya
M N
MN
Institute of New Antibiotics, USSR Academy of Medical Sciences, Moscow.
Holpne-Kozlova
N V
NV
Lazhko
E I
EI
D000478:Alkylation; D008745:Methylation; D008826:Microbial Sensitivity Tests; D013308:Streptonigrin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship
C073938:tri-1',5',5'-N,N,N-mono-8'-O-methylstreptonigrone; C073939:di-2',8'-O-di-5',5'-N,N-methylstreptonigrone; D013308:Streptonigrin; C045696:streptonigrone