Synthesis and antibacterial activity of acylides (3-O-acyl-erythromycin derivatives):: A novel class of macrolide antibiotics

被引：52

作者：

Tanikawa, T

Asaka, T

Kashimura, M

Misawa, Y

Suzuki, K

Sato, M

Kameo, K

Morimoto, S

Nishida, A

机构：

[1] Taisho Pharmaceut Co Ltd, Med Res Labs, Omiya, Saitama 3308530, Japan

[2] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2001年 / 44卷 / 24期

关键词：

D O I：

10.1021/jm015566s

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Introduction of an acyl group to the 3-O-position of erythromycin A derivatives instead of L-cladinose led to a novel class of macrolide antibiotics that we named "acylides". The 3-O-nitrophenylacetyl derivative TEA0777 showed significantly potent activity against not only erythromycin-susceptible Gram-positive pathogens but also inducibly macrolides-lincosamides-streptogramin B (MLSB)-resistant Staphylococcus aureus and efflux-resistant Streptococcus pneumoniae. These results indicated that acylides have potential as next-generation macrolide antibiotics.

引用

收藏

页码：4027 / 4030

页数：4

相关论文

共 23 条

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

BRIGHT, GM ;

NAGEL, AA ;

BORDNER, J ;

DESAI, KA ;

DIBRINO, JN ;

NOWAKOWSKA, J ;

VINCENT, L ;

WATROUS, RM ;

SCIAVOLINO, FC ;

ENGLISH, AR ;

RETSEMA, JA ;

ANDERSON, MR ;

BRENNAN, LA ;

BOROVOY, RJ ;

CIMOCHOWSKI, CR ;

FAIELLA, JA ;

GIRARD, AE ;

GIRARD, D ;

HERBERT, C ;

MANOUSOS, M ;

MASON, R .

JOURNAL OF ANTIBIOTICS, 1988, 41 (08) :1029-1047

[12] New directions in antibacterial research [J].

Chu, DTW ;

Plattner, JJ ;

Katz, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (20) :3853-3874

[13] ERYTHROMYCIN SERIES .11. RING EXPANSION F ERYTHROMYCIN-A OXIME BY THE BECKMANN REARRANGEMENT [J].

DJOKIC, S ;

KOBREHEL, G ;

LAZAREVSKI, G ;

LOPOTAR, N ;

TAMBURASEV, Z ;

KAMENAR, B ;

NAGL, A ;

VICKOVIC, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1881-1890

[14] ERYTHROMYCIN SERIES .12. ANTIBACTERIAL INVITRO EVALUATION OF 10-DIHYDRO-10-DEOXO-11-AZAERYTHROMYCIN-A - SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP OF ITS ACYL DERIVATIVES [J].

DJOKIC, S ;

KOBREHEL, G ;

LAZAREVSKI, G .

JOURNAL OF ANTIBIOTICS, 1987, 40 (07) :1006-1015

[15] ERYTHROMYCIN MIMICS EXOGENOUS MOTILIN IN GASTROINTESTINAL CONTRACTILE ACTIVITY IN THE DOG [J].

ITOH, Z ;

NAKAYA, M ;

SUZUKI, T ;

ARAI, H ;

WAKABAYASHI, K .

AMERICAN JOURNAL OF PHYSIOLOGY, 1984, 247 (06) :G688-G694

[16]

*JAP SOC CHEM, 1981, CHEMOTHERAPY, V29, P76

[17] Synthesis and antibacterial activity of the tricyclic ketolides TE-802 and its analogs [J].

Kashimura, M ;

Asaka, T ;

Misawa, Y ;

Matsumoto, K ;

Morimoto, S .

JOURNAL OF ANTIBIOTICS, 2001, 54 (08) :664-678

[18] AROMATIC ESTERS OF 5-0-DESOSAMINYLERYTHRONOLIDE A-OXIME [J].

LEMAHIEU, RA ;

CARSON, M ;

KIERSTEAD, RW ;

PESTKA, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (08) :849-851

[19] CHEMICAL MODIFICATION OF ERYTHROMYCINS .1. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 6-O-METHYLERYTHROMYCINS-A [J].

MORIMOTO, S ;

TAKAHASHI, Y ;

WATANABE, Y ;

OMURA, S .

JOURNAL OF ANTIBIOTICS, 1984, 37 (02) :187-189

[20]

MORIMOTO S, 1987, Patent No. 4670549