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N-Substituted derivatives of 23-amino-4',23-dideoxymycaminosyl tylonolide. Synthesis and antibacterial activity. 1985

S Sakamoto, and T Tsuchiya, and A Tanaka, and S Umezawa, and M Hamada, and H Umezawa

23-Amino-4',23-dideoxymycaminosyl tylonolide diethyl acetal (5) has been prepared from 4',23-dideoxy-23-iodomycaminosyl tylonolide diethyl acetal (3) by treatment with sodium azide followed by selective reduction of the resulting azide (4). 23-Acylamino-23-deoxy (6 approximately 8) and 23-deoxy-23-urethane-type compounds (12 approximately 15) were further prepared. Treatment of the 23-alkylamino-4',23-dideoxymycaminosyl tylonolides (9, 10) with chloroformates gave 23-N-alkyl-23-deoxy-23-urethane-type compounds (16 approximately 21, 29, 30). 23-N-Alkyl-23-deoxy-23-(2-hydroxyethalamino and 2-methoxyethylamino)-4',23-dideoxymycaminosyl tylonolides (22 approximately 25, 27, 28) were prepared from 3 and the corresponding amines. Antibacterial activities and toxicities (for 23 and 27) of these compounds are described. toxicities (for 23 and 27) of these compounds are described.

UI MeSH Term Description Entries
D007933 Leucomycins An antibiotic complex produced by Streptomyces kitasatoensis. The complex consists of a mixture of at least eight biologically active components, A1 and A3 to A9. Leucomycins have both antibacterial and antimycoplasmal activities.
D001419 Bacteria One of the three domains of life (the others being Eukarya and ARCHAEA), also called Eubacteria. They are unicellular prokaryotic microorganisms which generally possess rigid cell walls, multiply by cell division, and exhibit three principal forms: round or coccal, rodlike or bacillary, and spiral or spirochetal. Bacteria can be classified by their response to OXYGEN: aerobic, anaerobic, or facultatively anaerobic; by the mode by which they obtain their energy: chemotrophy (via chemical reaction) or PHOTOTROPHY (via light reaction); for chemotrophs by their source of chemical energy: CHEMOLITHOTROPHY (from inorganic compounds) or chemoorganotrophy (from organic compounds); and by their source for CARBON; NITROGEN; etc.; HETEROTROPHY (from organic sources) or AUTOTROPHY (from CARBON DIOXIDE). They can also be classified by whether or not they stain (based on the structure of their CELL WALLS) with CRYSTAL VIOLET dye: gram-negative or gram-positive. Eubacteria
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

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