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


Collin, M P; Hobbie, S N; Böttger, E C; Vasella, A (2009). Synthesis and Evaluation of S- and C(1)-Substituted Analogues of Lincomycin. Helvetica Chimica Acta, 92(2):230-266.

Abstract

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.

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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:04 Faculty of Medicine > Institute of Medical Microbiology
Dewey Decimal Classification:570 Life sciences; biology
610 Medicine & health
Language:English
Date:2009
Deposited On:06 Oct 2009 07:30
Last Modified:05 Apr 2016 13:22
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Publisher DOI:10.1002/hlca.200800343
Permanent URL: http://doi.org/10.5167/uzh-21095

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