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Synthesis and antibacterial activities of a novel alkylide: 3-O-(3-aryl-2-propargyl) and 3-O-(3-aryl-2-propenyl)clarithromycin derivatives
- Source :
- Bioorganicmedicinal chemistry letters. 20(9)
- Publication Year :
- 2009
-
Abstract
- A series of novel 3-O-(3-aryl-E-2-propenyl)clarithromycin derivatives 8 and 3-O-(3-aryl-2-propargyl)clarithromycin derivatives 11 were designed, synthesized, and evaluated for their in vitro antibacterial activities. Compared with 8c and 11c (Ar was 5-pyrimidyl), 3-O-(3-(5′-pyrimidyl)-Z-1-propenyl) counterpart 6c displayed 4- to 64-fold more potent activities against erythromycin-susceptible Staphylococcus aureus and Streptococcus pneumoniae. Moreover, the activities of 6c, 8c, and 11c against erythromycin-resistant S. aureus and S. pneumoniae were in general 4-fold higher than those of the reference compound, clarithromycin and azithromycin.
- Subjects :
- Staphylococcus aureus
Stereochemistry
Clinical Biochemistry
Pharmaceutical Science
Sonogashira coupling
Erythromycin
Microbial Sensitivity Tests
medicine.disease_cause
Biochemistry
chemistry.chemical_compound
Structure-Activity Relationship
Clarithromycin
Drug Discovery
Streptococcus pneumoniae
medicine
Molecular Biology
Propenyl
Aryl
Organic Chemistry
Anti-Bacterial Agents
chemistry
Propargyl
Molecular Medicine
medicine.drug
Subjects
Details
- ISSN :
- 14643405
- Volume :
- 20
- Issue :
- 9
- Database :
- OpenAIRE
- Journal :
- Bioorganicmedicinal chemistry letters
- Accession number :
- edsair.doi.dedup.....20a1050e13ed857210fb7129a7517b2b