کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1373503 981898 2007 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis and biological activity of enantiomeric pairs of 5-vinylthiolactomycin congeners
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis and biological activity of enantiomeric pairs of 5-vinylthiolactomycin congeners
چکیده انگلیسی

Twelve enantiomeric pairs of 5-vinylthiolactomycin congeners were synthesized by employing our efficient synthetic route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. From the biological activity assay carried out using the obtained congeners along with enantiomeric pairs of thiolactomycin and its 3-demethyl derivative previously prepared, it appeared evident that in vitro antibacterial and mammalian type I FAS inhibitory activity of thiolactomycin congeners can be cleanly separated by changing not only the structure but also the absolute configuration of the side chain at the C5-position. These studies led us to explore (S)-3-demethyl-5-(pent-1-enyl)thiolactomycin derivative [(S)-4-hydroxy-5-methyl-5-(pent-1-enyl)-5H-thiophen-2-one] which exhibits type I FAS inhibitory activity equal to that of C75, the potent inhibitor so far reported, with complete loss of in vitro antibacterial activity.

Among 3a–f, ent-3a–f, 4a–f, and ent-4a–f produced, (S)-3-demethyl-5-(pent-1-enyl)thiolactomycin derivative (ent-4d) exhibited mammalian type I FAS inhibitory activity equal to that of C75, the potent inhibitor so far reported, with complete loss of in vitro antibacterial activity.Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 17, Issue 14, 15 July 2007, Pages 4070–4074
نویسندگان
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