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Synthesis and Evaluation of S- and C(1)-Substituted Analogues of Lincomycin

✍ Scribed by Marie-Pierre Collin; Sven N. Hobbie; Erik C. Böttger; Andrea Vasella

Publisher
John Wiley and Sons
Year
2009
Tongue
German
Weight
479 KB
Volume
92
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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New thioglycosides and C(1)‐alkylated thioglycosides (S‐ulosides) of lincomycin were synthesized, and their antibiotic activities were determined. The S‐aryl and S‐arylalkyl analogues 11a–11i were obtained by S‐glycosylation of the sulfoxides 7 with arenethiols, or by S‐alkylation of the thiol 14 with alkyl bromides. Lincomycin derivatives 27, 32a, 32b, 38a, 38b, 44, and 47 were prepared via Henry reaction or Michael addition of the lincosamine‐derived 1‐deoxy‐1‐nitropyranoses 22. The S‐alkyl derivatives showed a similar activity and specificity as lincomycin. Lipophilic S‐uloside analogues were two‐ to fourfold less active than the parent antibiotic, whilst the hydrophilic analogues were inactive.

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