Synthesis of 6-O-methyl-azithromycin and its ketolide analogue via Beckmann rearrangement of 9(E)-6-O-methyl-erythromycin oxime

被引：16

作者：

Denis, A

Agouridas, C

机构：

[1] Hoechst Mar Roussel, Romainville Res Ctr, Dept Med Chem, F-93235 Romainville, France

[2] Hoechst Mar Roussel, Romainville Res Ctr, Core Res Funct Dept, F-93235 Romainville, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 18期

关键词：

D O I：

10.1016/S0960-894X(98)00402-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of 6-O-methyl-azithromycin and its aza-ketolide analogue have been achieved by carrying out the Beckmann rearrangement of the readily available 9(E)-6-O-methyl-erythromycin oxime 1. In contrast to the C14 ketolides like HMR 3647, the aza-ketolide turns out to be inactive, thus demonstrating that the addition of a 3 keto function and ring expension, from 14 to 15 membered ring, could be deleterious for the antibacterial activity, (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2427 / 2432

页数：6

共 15 条

[1]

AGOURIDAS C, 1995, 35 INT C ANT AG CHEM

[2]

AGOURIDAS C, 1997, 37 INT C ANT AG CHEM

[3]

AGOURIDAS C, 1994, 34 INT C ANT AG CHEM

[4] SYNTHESIS, INVITRO AND INVIVO ACTIVITY OF NOVEL 9-DEOXO-9A-AZA-9A-HOMOERYTHROMYCIN A DERIVATIVES - A NEW CLASS OF MACROLIDE ANTIBIOTICS, THE AZALIDES [J].