874-24-8

Usage

InChI:InChI=1/C6H5NO3/c8-4-2-1-3-7-5(4)6(9)10/h1-3,8H,(H,9,10)/p-1

Upstream product

• 1849-55-4 2-Formyl-3-hydroxypyridin 
• 98-98-6 2-Picolinic acid 
• 98140-94-4 3-amino-2-picolinehydroxamic acid 
• 76045-30-2 (S)-4,5-dihydro-2-(3-hydroxy-2-pyridinyl)-4-methyl-4-thiazolecarboxylic acid 
• 27507-15-9 ethyl 3-aminopyridine-2-carboxylate 
• 56-87-1 L-lysine 
• 932-35-4 3-hydroxypyridine-2-carbonitrile 
• 109-00-2 3-HYDROXYPYRIDINE 
• 6602-28-4 3-hydroxypyridine N-oxide 
• 1121-25-1 2-methyl-3-pyridinol 
• 1462-86-8 3-amino-pyridine-2-carboxylic acid 
• 1121-60-4 pyridine-2-carbaldehyde 

Downstream Products

• 109-00-2 3-HYDROXYPYRIDINE 
• 14764-90-0 2,6-diiodo-3-hydroxypyridine 
• 73406-50-5 ethyl 3-hydroxypyridine-2-carboxylate 
• 56879-47-1 3-hydroxypiperidine-2-carboxylic acid 
• 668-72-4 Virginiamycin S₁ 
• 208649-02-9 (+/-)-cis-3-hydroxypiperidine-2-carboxylic acid 
• 160938-52-3 N-(2,6-diisopropyl-phenyl)-3-hydroxy-picolinamide 
• 1082-59-3 3-hydroxy-pyridine-2-carboxylic acid anilide 
• 85567-41-5 3-hydroxy-N-propylpyridine-2-carboxamide 
• 170689-52-8 3-benzyloxypyridine-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

In vitro reconstitution of the biosynthetic pathway of 3-hydroxypicolinic acid

3-Hydroxypicolinic acid (3-HPA) is an important pyridine building block of bacterial secondary metabolites. Although the main biosynthetic pathways of these metabolites have been identified and well characterized, the enzymatic mechanism underlying the biosynthesis of 3-HPA has yet to be elucidated. In this work, we successfully reconstituted the complete biosynthetic pathway of 3-HPA in vitro. We showed that an l-lysine 2-aminotransferase, a two-component monooxygenase, and a FAD-dependent dehydrogenase are required to convert l-lysine to 3-HPA. We further demonstrated that 3-HPA does not derive from the direct hydroxylation of the picolinic acid at C-3, but from a successive process of C-3 hydroxylation of the piperideine-2-carboxylic acid and tautomerization of the produced 3-hydroxyl dihydropicolinic acid. Therefore, this study unveils the unusual assembly logic of 3-HPA and sheds light on the potential of engineering the 3-HPA pathway for generating novel pyridine-based building blocks.

Method for synthesizing 3-hydroxy-2-picolinic acid and derivatives thereof

The invention discloses an effective synthesis method of 3-hydroxy-2-picolinic acid and derivatives thereof. The method comprises an oxidation reaction, a cyanation reaction and a hydrolysis reaction.According to the oxidation reaction, 3-hydroxypyridine as shown in a formula I and derivatives thereof are used as substrates, and under the condition that an aqueous hydrogen peroxide solution is used as an oxidizing agent, the reaction is performed in glacial acetic acid at 60 DEG C in a nitrogen environment to obtain an oxidation product as shown in a structural general formula II. According to the cyanation reaction, the compound II and trimethylsilyl cyanide are taken as substrates and mixed with dimethylaminoformyl chloride in an ice bath, and then the reaction is conducted in dichloromethane at room temperature in the nitrogen environment to obtain a cyanation product as shown in a structural general formula III. According to the hydrolysis reaction, with the product as shown in the formula III as a substrate, the reaction is conducted in ethanol at a temperature of 80 DEG C under the condition of an aqueous sodium hydroxide solution to obtain the 3-hydroxy-2-picolinic acid asshown in the structural general formula IV and the derivatives thereof. The method is relatively economical, reaction universality is good, gram-level preparation is easy to carry out, the whole process can be industrialized, and reaction conditions are green.

Kinetics of oxidation of heterocyclic compounds by quinolinium dichromate

Quinolinium dichromate in sulfuric acid oxidized heterocyclic aldehydes (to the corresponding acids) and heterocyclic carboxylic acids (to the corresponding hydroxy-substituted acids) in acetic acidwater medium (vol. ratio, v(water)/v(acetic acid) = 50:50). The kinetic results supported a mechanistic pathway proceeding via a rate-determining decomposition of the chromate ester.

Kinetic studies on the quinolinium dichromate oxidation of heteroacids

Heterocyclic carboxylic acids reacted with quinolinium dichromate, in sulfuric acid, to yield the corresponding hydroxy-substituted acids. The kinetic results supported a mechanistic pathway proceeding via the rate-determining formation of the cyclic chromate ester.

3-Hydroxy-4-oxo-3,4-dihydro-5-azabenzo-1,2,3-triazene

The known but long-neglected compound HODhat was shown to be in certain situations a useful peptide coupling additive. Uronium and phosphonium salts with HODhat built into the system were also useful stand-alone coupling reagents. Comparisons with related additives and coupling reagents showed that the new systems were sometimes more and sometimes less effective than previously described systems in the case of stepwise and segment couplings. Applications to assembly of the model decapeptide ACP showed that HDATU was far more effective than HDTU and more effective than HATU under some conditions.

Quinolinium dichromate oxidation of heterocyclic carboxylic acids

Heterocyclic carboxylic acids were oxidized to the corresponding hydroxy-substituted acids by quinolinium dichromate in sulfuric acid, in 50% (v/v) acetic acid-water as solvent. The kinetic results supported a mechanistic pathway proceeding via a rate-determining decomposition of the chromate ester.

Effects of C-4 stereochemistry and C-4' hydroxylation on the iron clearing efficiency and toxicity of desferrithiocin analogues

Additional structure-activity studies of desferrithiocin analogues are carried out. The effects of stereochemistry at C-4 on the ligands' iron clearing efficiency are reviewed and assessed using the enantiomers 4,5- dihydro-2-(2,4-dihydroxyphenyl)thiazole-4(R)-carboxylic acid and 4,5-dihydro- 2-(2,4-dihydroxyphenyl)thiazole-4(S)-carboxylic acid. The utility of 4'- hydroxylation as a method of reducing the toxicity of desazadesferrithiocin analogues is also examined further with the synthesis and in vivo comparison of 4,5-dihydro-2-(2-hydroxyphenyl)-4-methylthiazole-4(S)-carboxylic acid, which is the natural product 4-methylaeruginoic acid, and 4,5-dihydro-2- (2,4-dihydroxyphenyl)-4-methylthiazole-4(S)-carboxylic acid. The stereochemistry at C-4 is shown to have a substantial effect on the iron clearing efficiency of desferrithiocin analogues, as does C-4'-hydroxylation on the toxicity profile. All of the compounds are evaluated in a bile-duct- cannulated rodent model to determine iron clearance efficiency and are carried forward to the iron-overloaded primate for iron clearing measurements. On the basis of the results of the present work, although 4,5- dihydro-2-(2,4-dihydroxyphenyl)thiazole-4(S)-carboxylic acid is still the most promising candidate for clinical evaluation, 4,5-dihydro-2-(2,4- dihydroxyphenyl)4-methylthiazole-4(S)-carboxylic acid (4'- hydroxydesazadesferrithiocin) also merits further preclinical assessment.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF IMMUNOMEDIATED INFLAMMATORY DISORDERS

Compositions and methods for the prevention and treatment of immunomediated inflammatory disorders, especially for those disorders associated with the respiratory tract, are provided. More particularly, a tryptase inhibitor, typically a hydroxyaroyl or hydroxyheteroaroyl substituted dipeptide, is administered. Also provided by this invention are pharmaceutical compositions, typically aerosol or topical, as well as aerosol devices for administering these compositions intranasally.

2-Pyridyl-2-thiazoline-4-carboxylic acid derivatives

The invention relates especially to 2-(3'-hydroxypyrid-2'-yl)-2-thiazoline-4-carboxylic acid derivatives of the formula (I) and salts and also certain metal complexes of these compounds, processes for their manufacture, pharmaceutical agents containing such compounds and the use of these compounds. STR1 In the formula, R1 represents free, etherified or esterified hydroxy, R2 represents hydrogen or an aliphatic, carbocyclic or carbocyclic-aliphatic radical having 1-12 carbon atoms, and R3 represents hydrogen or an unsubstituted aliphatic radical having 1-7 carbon atoms. The compounds of the formula (I) can be used, for example, for the abstraction of heavy metals from the organism of warm-blooded animals and/or they have an antibiotic action.