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Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2008 Oct 01; Vol. 130 (39), pp. 13110-9. Date of Electronic Publication: 2008 Sep 05. - Publication Year :
- 2008
-
Abstract
- The molecular design, chemical synthesis, and biological evaluation of two distinct series of platensimycin analogues with varying degrees of complexity are described. The first series of compounds probes the biological importance of the benzoic acid subunit of the molecule, while the second series explores the tetracyclic cage domain. The biological data obtained reveal that, while the substituted benzoic acid domain of platensimycin is a highly conserved structural motif within the active compounds with strict functional group requirements, the cage domain of the molecule can tolerate considerable structural modifications without losing biological action. These findings refine our present understanding of the platensimycin pharmacophore and establish certain structure-activity relationships from which the next generation of designed analogues of this new antibiotic may emerge.
- Subjects :
- Adamantane analogs & derivatives
Adamantane chemical synthesis
Aminobenzoates chemical synthesis
Anilides chemical synthesis
Aniline Compounds chemical synthesis
Aniline Compounds chemistry
Anti-Infective Agents chemical synthesis
Benzaldehydes chemistry
Benzoates chemical synthesis
Benzoates chemistry
Benzoates pharmacology
Benzodioxoles chemistry
Cyclohexenes chemical synthesis
Cyclohexenes chemistry
Drug Design
Epoxy Compounds chemical synthesis
Epoxy Compounds chemistry
Methicillin Resistance
Microbial Sensitivity Tests
Pyrans chemical synthesis
Pyrans chemistry
Staphylococcus aureus drug effects
Structure-Activity Relationship
Adamantane chemistry
Adamantane pharmacology
Aminobenzoates chemistry
Aminobenzoates pharmacology
Anilides chemistry
Anilides pharmacology
Anti-Infective Agents chemistry
Anti-Infective Agents pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 130
- Issue :
- 39
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 18771264
- Full Text :
- https://doi.org/10.1021/ja8044376