Synthesis of new thiazole analogues of pyochelin, a siderophore of Pseudomonas aeruginosa and Burkholderia cepacia.: A new conversion of thiazolines into thiazoles

被引：51

作者：

Mislin, GL ^{[1
]}

Burger, A ^{[1
]}

Abdallah, MA ^{[1
]}

机构：

[1] Ecole Super Biotechnol Strasbourg, CNRS, UPR 9050, Dept Recepteurs & Prot Membranaires,Lab Chim Micr, F-67400 Illkirch Graffenstaden, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 52期

关键词：

pseudomonas; siderophore; pyochelin; yersiniabactin; HPTT-COOH; thiazole; thiazoline; Weinreb amide;

D O I：

10.1016/j.tet.2004.10.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three pyochelin analogues and their methyl esters all containing a thiazole ring have been synthesised from the same Weinreb amide key intermediate. One of these analogues called HPTT-COOH, a molecule released in the course of pyochelin and yersiniabactin biosynthesis, was efficiently synthesised using a new base induced conversion of the key compound 2'-(2-hydroxyphenyl)-2'-thiazoline-4'-(N-methoxy,N-methyl) carboxamide into 2'-(2-hydroxyphenyl)-2'-thiazole-4'-(N-methoxy,N-methyl) carboxamide. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：12139 / 12145

页数：7

共 29 条

[1] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF PYOCHELIN, A SIDEROPHORE OF PSEUDOMONAS-AERUGINOSA [J].