Waddell S T, Santorelli G M, Blizzard T A, Graham A, Occi J
Department of Medicinal Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA.
Bioorg Med Chem Lett. 1998 Mar 3;8(5):549-54. doi: 10.1016/s0960-894x(98)00070-5.
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.
已制备了一系列9-脱氧-8a-氮杂-8a-高红霉素的O-甲基衍生物，并对其抗菌活性进行了评估。将2',3'-双-Cbz保护的9-脱氧-8a-氮杂-8a-高红霉素中四个可利用羟基（4"、6、11和12）的相对甲基化速率与已发表报告中类似保护的9a-氮杂内酯的甲基化速率进行了比较。结果的不一致促使对9a-氮杂内酯的O-甲基化进行重新研究，并发现了已发表报告中结构归属的错误：报告为6-O-甲基-9a-氮杂内酯的化合物经测定为12-O-甲基衍生物。
