828936-79-4

Upstream product

• 554409-14-2 2-(2-hydroxy-phenyl)-4,5-dihydro-thiazole-4-carboxylic acid methoxy-methyl-amide 
• 115921-06-7 (R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid 
• 262419-96-5 (4R)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid N-methoxy-N-methylamide 
• 611-20-1 salicylonitrile 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 27501-91-3 2-(2-hydroxyphenyl)thiazole-4-carboxylic acid 
• 115921-07-8 (R)-2-(2'-hydroxyphenyl)-4-methoxycarbonyl-4,5-dihydrothiazole 
• 27501-92-4 methyl 2-(2-hydroxyphenyl)thiazole-4-carboxylate 

Downstream Products

• 83053-39-8 2'-(2-hydroxyphenyl)-2'-thiazole-4'-carboxaldehyde 
• 885279-11-8 2-(2-methoxyphenyl)thiazole-4-carbaldehyde 

Relevant academic research and scientific papers

Synthesis and Investigation of the Abiotic Formation of Pyonitrins A-D

Pyonitrins A-D are recently isolated natural products from the insect-associated Pseudomonas protegens strain, which were isolated from complex fractions that exhibited antifungal activity via an in vivo murine candidiasis assay. Genomic studies of Pseudomonas protegens suggested that pyonitrins A-D are formed via a spontaneous nonenzymatic reaction between biosynthetic intermediates of two well-known natural products pyochelin and pyrrolnitrin. Herein we have accomplished the first biomimetic total synthesis of pyonitrins A-D in three steps and studied the nonenzymatic formation of the pyonitrins using 15N NMR spectroscopy.

Synthesis and biological properties of thiazole-analogues of pyochelin, a siderophore of Pseudomonas aeruginosa

Pyochelin is a siderophore common to all strains of Pseudomonas aeruginosa utilized by this Gram-negative bacterium to acquire iron(III). FptA is the outer membrane transporter responsible of ferric-pyochelin uptake in P. aeruginosa. We describe in this Letter the synthesis and the biological properties ( 55Fe uptake, binding to FptA) of several thiazole analogues of pyochelin. Among them we report in this Letter the two first pyochelin analogues able to bind FptA without promoting any iron uptake in P. aeruginosa.

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

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. Graphical Abstract