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Chemical Compound Review:

Desmycosin 2-[ (2R,3S,4E,6E,9R,11R,12S,13S,14 R)-12...

Synonyms: Tylosin B, CHEMBL43441, AC1O5OFO, C01687, 11032-98-7

Mutak, S. et al., Kirst, H.A. et al., Iveković, D. et al., Kirst, H.A. et al., Debono, M. et al., et al.

Iveković, Lopotar, Brajsa, Mandić,

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Disease relevance of Tylosin B

Certain 20-modified derivatives of desmycosin demonstrated good oral bioavailability in chicks and a lead compound with oral efficacy in the Pasteurella infection model was discovered [1].

High impact information on Tylosin B

Semisynthetic macrolide antibacterials derived from tylosin. Synthesis and structure-activity relationships of novel desmycosin analogues [2].
To evaluate the importance of the C-3 position of desmycosin for biological activity, the C-3 substituted derivatives were synthesized by a standard sequence of protective group chemistry followed by Wittig reaction and esterification as the key steps [2].
Evaluation of in vitro and in vivo antimicrobial activity indicated that derivatives of demycarosyltylosin (desmycosin) combined the broadest spectrum of antimicrobial activity with the best efficacy and bioavailability after oral administration [3].
The results obtained show that dimerization and two electron reduction of desmycosin occur in parallel yielding a symmetric dimer at position C13 and 10,11-dihydrodesmycosin as the end products [4].
The most useful activity was found within a series of derivatives produced by reductive amination of desmycosin with secondary amines [5].

Associations of Tylosin B with other chemical compounds

A series of 20-deoxo-20-cyclic (alkylamino) derivatives of tylosin, desmycosin, macrocin and lactenocin was prepared by reductive amination of the C-20 aldehyde group [6].

References

In vitro and in vivo evaluation of C-20- and C-23-modified derivatives of tylosin against veterinary pathogens. Kirst, H.A., Ose, E.E., Toth, J.E., Willard, K.E., Debono, M., Felty-Duckworth, A.M., Pekarek, R.S. J. Antibiot. (1988) [Pubmed]
Semisynthetic macrolide antibacterials derived from tylosin. Synthesis and structure-activity relationships of novel desmycosin analogues. Mutak, S., Marsić, N., Kramarić, M.D., Pavlović, D. J. Med. Chem. (2004) [Pubmed]
Synthesis and evaluation of tylosin-related macrolides modified at the aldehyde function: a new series of orally effective antibiotics. Kirst, H.A., Toth, J.E., Debono, M., Willard, K.E., Truedell, B.A., Ott, J.L., Counter, F.T., Felty-Duckworth, A.M., Pekarek, R.S. J. Med. Chem. (1988) [Pubmed]
Electrochemical reduction of desmycosin, structure investigation and antibacterial evaluation of the resulting products. Iveković, D., Lopotar, N., Brajsa, K., Mandić, Z. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. (2003) [Pubmed]
Structure-activity studies of 20-deoxo-20-amino derivatives of tylosin-related macrolides. Kirst, H.A., Willard, K.E., Debono, M., Toth, J.E., Truedell, B.A., Leeds, J.P., Ott, J.L., Felty-Duckworth, A.M., Counter, F.T., Ose, E.E. J. Antibiot. (1989) [Pubmed]
Synthesis and antimicrobial evaluation of 20-deoxo-20-(3,5-dimethylpiperidin-1-yl)desmycosin (tilmicosin, EL-870) and related cyclic amino derivatives. Debono, M., Willard, K.E., Kirst, H.A., Wind, J.A., Crouse, G.D., Tao, E.V., Vicenzi, J.T., Counter, F.T., Ott, J.L., Ose, E.E. J. Antibiot. (1989) [Pubmed]

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