Novel antibacterial azetidine lincosamides

Bioorganic & Medicinal Chemistry Letters
2008.0

Abstract

The synthesis and evaluation of novel azetidine lincosamides 1 are described. Eleven new (3-trans-alkyl)azetidine-2-carboxylic acids were synthesized via alkylation of N-TBS-4-oxo-azetidine-2-carboxylic acid and subsequent elaboration then coupled to 7-chloro-1-methylthio-lincosamine. The resulting lincosamides differ from the drug clindamycin in both the size of the ring and the position/structure of the alkyl side-chain. SAR within the series was explored with attention to alkyl variants in positions 1 and 3 of the azetidine ring.

Knowledge Graph

Similar Paper

Novel antibacterial azetidine lincosamides
Bioorganic & Medicinal Chemistry Letters 2008.0
Synthesis and Antibacterial Activity of a Novel Class of 15-Membered Macrolide Antibiotics, “11a-Azalides”
ACS Medicinal Chemistry Letters 2011.0
Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels–Alder chemistry
Bioorganic & Medicinal Chemistry Letters 2010.0
Design, synthesis and biological evaluation of novel azaspiro analogs of linezolid as antibacterial and antitubercular agents
European Journal of Medicinal Chemistry 2016.0
Synthesis of novel macrolide derivatives with imidazo[4,5-b]pyridinyl sulfur contained alkyl side chains and their antibacterial activity
Bioorganic & Medicinal Chemistry Letters 2009.0
N/C-4 substituted azetidin-2-ones: Synthesis and preliminary evaluation as new class of antimicrobial agents
Bioorganic & Medicinal Chemistry Letters 2007.0
Synthesis and antibacterial activity of linezolid analogues
Bioorganic & Medicinal Chemistry Letters 2002.0
Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction: SAR studies on conformationally constrained analogues of Linezolid
Bioorganic & Medicinal Chemistry Letters 2006.0
The synthesis and antibacterial activity of 1,3,4-Thiadiazole phenyl oxazolidinone analogues
Bioorganic & Medicinal Chemistry Letters 2003.0
Azetidinone-isothiazolidinones: Stereoselective synthesis and antibacterial evaluation of new monocyclic beta-lactams
Bioorganic & Medicinal Chemistry 2010.0