554409-14-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Thiazolecarboxamide, 4,5-dihydro-2-(2-hydroxyphenyl)-N-methoxy-N-methylis used as an intermediate in the synthesis of Pyochelin I and Pyochelin II, which are siderophores produced by Pseudomonas aeruginosa PAO1. These siderophores play a crucial role in the assimilation of iron, which is essential for the growth and survival of the bacteria.
Used in Environmental Applications:
4-Thiazolecarboxamide, 4,5-dihydro-2-(2-hydroxyphenyl)-N-methoxy-N-methylis used for its triphenyltin (T809350) decomposition capacity. This property can be utilized in environmental applications to break down harmful compounds and reduce their impact on the ecosystem.

Upstream product

• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 115921-06-7 (R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid 
• 611-20-1 salicylonitrile 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 338461-14-6 (2R)-3-hydroxy-2-(2-hydroxythiobenzoylamino)-N-methoxy-N-methylpropionamide 
• 338461-18-0 (2R)-3-hydroxy-N-methoxy-2-(2-methoxybenzoylamino)-N-methylpropionamide 
• 338461-19-1 (2R)-3-hydroxy-2-(2-hydroxybenzoylamino)-N-methoxy-N-methylpropionamide 
• 338461-17-9 (2R)-2-tert-butoxycarbonylamino-N-methoxy-3-(2-methoxybenzyloxy)-N-methylpropionamide 
• 143209-04-5 (S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid 
• 101821-30-1 2-(2′-hydroxyphenyl)-2-thiazoline 

Relevant academic research and scientific papers

Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+Complex

The siderophore piscibactin is a key virulence factor involved in the iron uptake of pathogenic bacteria Photobacterium damselae subsp. piscicida and Vibrio anguillarum, responsible for the fish diseases photobacterioisis (pasteurellosis) and vibriosis, respectively. A convergent total synthesis of its Ga3+ complex using l-/d-cysteine as chiral agents and Meldrum's acid is described. A Staudinger reduction/Aza-Wittig process in the synthesis of the acid-sensitive β-hydroxy-2,4-disubstituted thiazoline moiety and the convenient protecting groups was a key step in this synthesis.

Biologically Inspired Total Synthesis of Ulbactin F, an Iron-Binding Natural Product

Natural products from environmental microbiomes provide exquisite templates for elucidating biological activity in the search for new drugs. A recently discovered marine Brevibacillus sp. metabolite, ulbactin F, was found to inhibit tumor cell migration a

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.

A Short stereoselective synthesis of prepiscibactin using a SmI2-mediated reformatsky reaction and zn2+-induced asymmetric thiazolidine formation

Prepiscibactin (1) is a possible intermediate in the biosynthesis of piscibactin, the siderophore responsible for the iron uptake of the bacterium Photobacterium damselae subsp. piscicida, the aethiological agent of fish pasteurellosis. Compound 1 was syn

Synthesis of fluorescent probes based on the pyochelin siderophore scaffold

Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3′′-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.(Figure Presented)

Bacterial siderophores: Synthesis and biological activities of novel pyochelin analogues

The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3″N-Boc-pyochelin, 3″-nor-NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these

Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin

Total synthesis of yersiniabactin, a siderophore from cultures of the bacterium Yersinia enterocolitica, was accomplished. Chirality at the readily racemizable C-9 carbon was preserved during cyclization of β-hydroxythioamide by means of Burgess reagent leading to thiazoline. Based on its synthesis, the absolute configuration of natural yersiniabactin has been determined as 9R, 10RS, 12R, 13S and 19S.

An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia

A considerably improved stereocontrolled synthesis of pyochelin, a hydroxyphenylthiazolinylthiazolidine type of siderophore common to most strains of Pseudomonas aeruginosa and Burkholderia cepacia is described. 2'- (2-Hydroxyphenyl)-2'-thiazoline-4'-carboxaldehyde, a key molecule involved in this synthesis has been prepared by reduction of 2'-(2-hydroxyphenyl)-2'- thiazoline-4'-(N-methoxy,N-methyl) carboxamide with lithium aluminium hydride. The aldehyde was further coupled with (R)-N-methylcysteine to yield pyochelin. Under the conditions reported, epimerization at the C-4' center was considerably diminished.