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3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity

Croatian International Relations Review

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Title 3-O-Acyl Derivatives of Bridged-15-Membered Azalides: Synthesis, Structural Determination and Antibacterial Activity
3-O-Acilni derivati premoštenih 15-članih azalida: priprava, određivanje strukture i antibakterijska aktivnost
 
Creator Fajdetić, Andrea
Kobrehel, Gabrijela
Lazarevski, Gorjana
Štimac, Vlado
Mutak, Stjepan
 
Subject azalides; synthesis; acylation; NMR spectroscopy
 
Description The synthesis, structural determination and biological evaluation of 15-membered azalides acylated at the C-3 position are described. 3-Descladinosyl-9a,l1-cyclic carbamate of the 9a-aza- 9a-homoerythromycin A and their 12-O-alkyl derivatives were synthesized via acidic hydrolysis of adequate 3-cladinosyl analogues. Protections of 2'-hydroxyl group were performed to furnish starting compounds for acylation of the C-3-hydroxyl group. After deprotection various 3-O-acyl derivatives were obtained and their structures confirmed by spectroscopic methods (IR, MS, NMR). The new compounds were evaluated in vitro against a panel of Gram-positive and Gram-negative bacteria and their activities compared with those of parent derivatives. The 3-O-acyl derivatives exhibited improved antibacterial activity, but it was lower than by standard macrolides.
Opisani su priprava, odre|ivanje strukture i biološka ispitivanja 15-članih azalida aciliranih na položaju C-3. Kiselom hidrolizom pripadajućih 3-kladinozil analoga pripravljeni su 3-dekladinozil-9a,l1-ciklički karbamat 9a-aza-9a-homoeritromicina A i njegovi 12-O-alkil derivati. Zaštićivanjem 2'-hidroksilne skupine pripravljeni su početni spojevi za aciliranje C-3-hidroksilne skupine. Nakon deprotekcije dobiveni su razni 3-O-acil derivati čije su strukture dokazane spektroskopskim metodama (IR, MS, NMR). Novi spojevi ispitani su in vitro na panelu Gram-pozitivnih i Gram-negativnih bakterija i njihove su aktivnosti uspore|ene s aktivnostima derivata osnovne supstance. 3-O-Acil derivati pokazuju poboljšanu antibakterijsku aktivnost, ali slabiju od aktivnosti standardnih makrolida.
 
Publisher Croatian Chemical Society
 
Date 2005-06-15
 
Type text
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
 
Format application/pdf
 
Identifier http://hrcak.srce.hr/26
http://hrcak.srce.hr/file/26
 
Source Croatica Chemica Acta
ISSN 0011-1643 (Print)
ISSN 1334-417X (Online)
Volume 78
Issue 2
 
Language eng
 
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