Synthesis and antibacterial activity of O-methyl derivatives of azalide antibiotics: I. 4″, 11 and 12-OMe derivatives via direct methylation

Bioorganic & Medicinal Chemistry Letters
1998.0

Abstract

A series of O-Me derivatives of 9-deoxo-8a-aza-8a-homoerythromycin has been prepared and evaluated for antibacterial activity. The relative rates of methylation of the four available hydroxyls (4", 6, 11 and 12) in 2',3'-bis-Cbz protected 9-deoxo-8a-aza-8a-homoerythromycin were compared to those given in a published report for the similarly protected 9a-azalide. An incongruity in the results prompted reinvestigation of the O-methylation of the 9a-azalide, and an error in structure assignment in the published report was discovered: the compound reported as the 6-OMe-9a-azalide has been determined to be the 12-OMe derivative.

Knowledge Graph

Similar Paper

Synthesis and antibacterial activity of O-methyl derivatives of azalide antibiotics: I. 4″, 11 and 12-OMe derivatives via direct methylation
Bioorganic & Medicinal Chemistry Letters 1998.0
Synthesis and antibacterial activity of O-methyl derivatives of azalide antibiotics: II. 6-OMe derivatives VIA clarithromycin
Bioorganic & Medicinal Chemistry Letters 1998.0
Synthesis and antibacterial activity of 3-O-carbamoyl derivatives of 6,11-di-O-methylerythromycin A: A novel class of acylides
European Journal of Medicinal Chemistry 2010.0
Synthesis and Antibacterial Activity of a Novel Class of 15-Membered Macrolide Antibiotics, “11a-Azalides”
ACS Medicinal Chemistry Letters 2011.0
Synthesis and antibacterial activities of 6-O-methylerythromycin A 9-O-(3-aryl-2-propenyl) oxime ketolide, 2,3-enol ether, and alkylide analogues
European Journal of Medicinal Chemistry 2010.0
Preparation and activities of 4″-epi and 4″-deoxy-4″-amino analogs derived from 9-deoxo-8a-aza-8a-homoerythromycin A
Bioorganic & Medicinal Chemistry Letters 1994.0
Synthesis and antibacterial activity of 4″,11-di-O-arylalkylcarbamoyl azithromycin derivatives
Bioorganic & Medicinal Chemistry Letters 2009.0
Synthesis of 6-O-methyl-azithromycin and its ketolide analogue via Beckmann rearrangement of 9(E)-6-O-methyl-erythromycin oxime
Bioorganic & Medicinal Chemistry Letters 1998.0
Novel 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 6-methoxy derivatives of 15-membered macrolides
Bioorganic & Medicinal Chemistry 2007.0
Novel 3-deoxy-3-descladinosyl-6-O-methyl erythromycin a analogues. Synthesis and in vitro activity
Bioorganic & Medicinal Chemistry Letters 1997.0