- An Approach to Modify 14-Membered Lactone Macrolide Antibiotic Scaffolds
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A ketolide derivative with (12R)-configuration was obtained via a novel ketene acetal in acidic conditions. The structure of this atypical β-keto ketene acetal intermediate within the macrocyclic system has been determined by NMR and X-ray methods. The use of basic conditions at an elevated temperature yielded new, doubly α,β-unsaturated ketone macrolide derivatives with (4E)-configuration as two conformational isomers of folded-in or folded-out conformations.
- Janas, Anna,Pyta, Krystian,Gdaniec, Maria,Przybylski, Piotr
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p. 3758 - 3761
(2022/02/07)
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- Synthesis of novel macrolide derivatives with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains and their antibacterial activity
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In an effort to find new antibiotics, a novel series of 14-membered macrolides with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains has been synthesized based on commercially available clarithromycin. Chemical transformation of hydroxy group at position C-3 afforded range of ketolides and acylides. Compared to telithromycin, compound 15a demonstrated improved in vitro activity against erythromycin-susceptible and -resistant strains.
- Xu, Peng,Liu, Lu,Chen, Xiao-zhuo,Li, Yun,Liu, Jian,Jin, Zhi-ping,Wang, Guang-qiang,Lei, Ping-sheng
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supporting information; experimental part
p. 4079 - 4083
(2010/04/24)
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- PROCESS FOR THE PRODUCTION OF TELITHROMYCIN
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The present invention relates to a process for the preparation of erythromysin derivatives, in particular telithromycin of formula (I) and its pharmaceutically acceptable salts, providing the isolated intermediates in crystalline form of superior stability and purity.
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Page/Page column 10; 17-18
(2009/05/28)
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- Synthesis and antibacterial activity of ketolides (6-O-methyl-3- oxoerythromycin derivatives): A new class of antibacterials highly potent against macrolide-resistant and -susceptible respiratory pathogens
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In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo- 6-O-methylerythromycin derivatives, so-called 'ketolides'. A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12- carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,-12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.
- Agouridas, Constantin,Denis, Alexis,Auger, Jean-Michel,Benedetti, Yannick,Bonnefoy, Alain,Bretin, Fran?ois,Chantot, Jean-Fran?ois,Dussarat, Arlette,Fromentin, Claude,D'Ambrières, Solange Gouin,Lachaud, Sylvette,Laurin, Patrick,Martret, Odile Le,Loyau, Véronique,Tessot, Nicole
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p. 4080 - 4100
(2007/10/03)
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