1452-77-3

Usage

Uses

Used in Molecular Imprinting:
PYRIDINE-2-CARBOXAMIDE is used as a template in the preparation of molecular imprinting polymer. This application is significant as it allows for the creation of highly selective and efficient materials for various purposes, including separation, sensing, and catalysis.
Used in Kinetics and Mechanism Studies:
PYRIDINE-2-CARBOXAMIDE has been utilized in a study to evaluate the kinetics and mechanism of liberation of picolinamide from chromium(III)-picolinamide complexes in HClO4. This research contributes to the understanding of the chemical behavior and interactions of picolinamide in different environments.
Used in Pharmaceutical Industry:
As a nicotinic acid derivative, PYRIDINE-2-CARBOXAMIDE is used for the prevention and treatment of cancer by activating the RUNX3 gene. This gene plays a crucial role in the regulation of cell differentiation and apoptosis, making it a potential target for cancer therapy. The activation of RUNX3 by picolinamide may help in the development of novel cancer treatments and improve patient outcomes.

Biological Activity

picolinamide is a poly (adp-ribose) synthetase (parp) inhibitor.parp inhibitors, a group of pharmacological inhibitors of the enzyme poly adp ribose polymerase (parp), are developed for multiple indications, especially for the treatment of cancer.

Biochem/physiol Actions

Picolinamide is potential inhibitor of poly (ADP-ribose) synthetase of nuclei from rat pancreatic islet cells. Picolinamide acts as bidentate ligand and forms complexes with lanthanide nitrates, thiocyanates and perchlorates.

in vitro

the pathway of oxidation of picolinamide by a gram-negative rod has been elucidated. results showed that under high ph conditions, whole cells could release 2,5-dihydroxypyridine into culture supernatants. moreover, sodium arsenite was able to cause whole cells to accumulate 6-hydroxypicolinate in the culture media. in addition, whole cells were found to oxidize picolinamide, without lag. it was also found that cell-free extracts could convert picolinamide into picolinate, and hydroxylate picolinate into 6-hydroxypicolinate [1].

in vivo

picolinamide was used in a previous study to evaluate the possibility that the inhibition of na+/phosphate cotransport might be associated with the inhibition of nad hydrolyzing enzymes. results showed that the overnight treatment of rats with picolinamide, administered as a single injection (4 mmol/kg), could inhibit na+/phosphate cotransport by isolated renal brush border membrane vesicles. similar to nicotinamide, the inhibition caused by picolinamide occurred in thyroparathyroidectomized rats, was specific for na+/phosphate cotransport. unlike nicotinamide, there was only a small 1.5-fold increase in renal cortical nad content after picolinamide treatment [2].

references

[1] c. g. orpin,m. knight, and w. c. evans. the bacterial oxidation of picolinamide, a photolytic product of diquatbiochem j. 1972 may; 127(5): 819–831.[2] campbell pi, al-mahrouq ha,abraham mi,kempson sa. specific inhibition of rat renal na+/phosphate cotransport by picolinamide. j pharmacol exp ther.1989 oct;251(1):188-92.

InChI:InChI=1/C22H17ClN2/c23-21-24-16-17-25(21)22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H

Upstream product

• 109-04-6 2-bromo-pyridine 
• 151-50-8 potassium cyanide 
• 4013-71-2 pyridine-2-carbonyl azide 
• 60072-19-7 3-phenylpyrido<2,1-f>-as-triazin-5-ium-1-olate 
• 110-86-1 pyridine 
• 109-09-1 2-chloropyridine 
• 201230-82-2 carbon monoxide 
• 1056640-24-4 pyridine-2-carboxylic acid {1-(2-nitrophenyl)-2-[(pyridine-2-ylmethyl)carbamoyl]ethyl}amide 
• 1121-60-4 pyridine-2-carbaldehyde 
• 109-06-8 α-picoline 
• 563-41-7 semicarbazide hydrochloride 
• 100-70-9 2-Cyanopyridine 
• 37746-78-4 4-bromo-trans-crotonic acid ethyl ester 
• 57665-05-1 sodium picolinate 

Downstream Products

• 82437-59-0 2,6-dimethyl-N-picolinoyl-4-oxo-4H-pyran-3-carboxamide 
• 82437-55-6 N-acetoacetylpicolinamide 
• 5346-38-3 pyridine-2-carbothioamide 
• 26972-40-7 1-vinylbenzimidazole 
• 1752-86-9 N-(p-tolyl)picolinamide 
• 10354-53-7 N-phenylpicolinamide 
• 149670-80-4 {PtCl(NC₅H₄CONH)(P(C₆H₅)3)} 
• 149670-81-5 {PtCl(NC₅H₄CONH)(P(C₆H₄CH₃)3)} 
• 1575753-93-3 N-(2-thiomorpholinophenyl)picolinamide 
• 1575754-01-6 N-(2-(4-hydroxypiperidin-1-yl)phenyl)picolinamide 
• 1575754-03-8 methyl 1-(2-(picolinamido)phenyl)piperidine-4-carboxylate 
• 1575754-06-1 tert-butyl (1-(2-(picolinamido)phenyl)piperidin-4-yl)carbamate 
• 100-70-9 2-Cyanopyridine 

Relevant academic research and scientific papers

Oxidative Coupling between Methylarenes and Ammonia: A Direct Approach to Aromatic Primary Amides

A direct oxidative amidation between methylarenes and aqueous ammonia using a tert-butyl hydroperoxide and tetrabutylammonium iodide (TBHP/TBAI) oxidation system with co-catalysis of iron(III) chloride has been developed. Both coupling partners were used in their native form to render prior functionalization unnecessary and afford a facile approach to aromatic primary amides.

Coupling of CH 3 OH and CO 2 with 2-cyanopyridine for enhanced yields of dimethyl carbonate over ZnO – CeO 2 catalyst

Abstract: The present work is aimed to produce dimethyl carbonate by coupling of CH 3OH and CO 2 with 2-cyanopyridine over ZnO–CeO 2 catalysts prepared by co-precipitation method. These catalysts were characterized by XRD, TEM, UV-Vis DRS, BET surface area, CO 2 and NH 3-TPD techniques and applied for the titled reaction. Among the investigated catalysts 10ZnO–90CeO 2 catalyst with CeO 2 crystallite size 8.0?nm exhibited 96% conversion of methanol with 99% selectivity to dimethyl carbonate. The superior catalytic activity is a unified effect of crystalline size of CeO 2 and presence of an optimum number of acidic and basic sites. This protocol offers enhanced conversion of methanol with the simultaneous conversion of 2-cyanopyridine into 2-picolinamide by removing water molecules formed in the reaction. Graphic Abstract: Incorporation of ZnO with CeO 2 enhanced the number of active sites, i.e., acidic and basic sites due to synergetic effect between ZnO and CeO 2. The role of 2-cyano pyridine is to act as a dehydrating agent for the removal of H 2O. [Figure not available: see fulltext.]

Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations

In this study, the first aza-Henry reaction of nitriles with nitromethane in a CuI/Cs2CO3/DBU system is described. The process was conveniently and directly used for the synthesis of β-aminonitroalkenes 2a-x and tolerated aryl-, alkyl-, hetaryl-, alkenyl-, and alkynylnitriles. The resulting aminonitroalkenes 2 could be successfully transformed to the corresponding 2-nitroacetophenones, 2-amino-1-halonitroalkenes, 2-alkylaminonitroalkenes, or 3-nitropyridines. In the presence of H2O, the aza-Henry reaction turned the reaction path to the nitrile hydration to exclusively yield the amides 3a-s.

Aqueous-Phase Nitrile Hydration Catalyzed by an In Situ Generated Air-Stable Ruthenium Catalyst

RuCl2(PTA)4 (PTA=1,3,5-triaza-7-phosphaadamantane) is an active, recyclable, air-stable, aqueous-phase nitrile hydration catalyst. The development of an in situ generated aqueous-phase nitrile hydration catalyst (RuCl3?3 H2O+6 equivalents PTA) is reported. The activity of the in situ catalyst is comparable to RuCl2(PTA)4. The effects of [PTA] on the activity of the reaction were investigated: the catalytic activity, in general, increases as the pH goes up, which shows a positive correlation with [PTA]. The pH effects were further explored for both the in situ and RuCl2(PTA)4 catalyzed reaction in phosphate buffer solutions with particular attention given to pH 6.8 buffer. Increased catalytic activity was observed at pH 6.8 versus water for both systems with turnover frequency (TOF) up to 135 h?1 observed for RuCl2(PTA)4 and 64 h?1 for the in situ catalyst. Catalyst loading down to 0.001 mol % was examined with turnover numbers as high as 22 000 reported. Similar to the preformed catalyst, RuCl2(PTA)4, the in situ catalyst could be recycled more than five times without significant loss of activity from either water or pH 6.8 buffer.

Substrate access tunnel engineering for improving the catalytic activity of a thermophilic nitrile hydratase toward pyridine and pyrazine nitriles

Nitrile hydratase (NHase) is able to bio-transform nitriles into amides. As nitrile hydration being an exothermic reaction, a NHase with high activity and stability is needed for amide production. However, the widespread use of NHase for amide bio-production is limited by an activity-stability trade-off. In this study, through the combination of substrate access tunnel calculation, residue conservative analysis and site-saturation mutagenesis, a residue located at the substrate access tunnel entrance of the thermophilic NHase from extremophile Caldalkalibacillus thermarum TA2. A1, βLeu48, was semi-rationally identified as a potential gating residue that directs the enzymatic activity toward various pyridine and pyrazine nitriles. The specific activity of the corresponding mutant βL48H towards 3-cyanopyridine, 2-cyanopyridine and cyanopyrazine were 2.4-fold, 2.8-fold and 3.1-fold higher than that of its parent enzyme, showing a great potential in the industrial production of high-value pyridine and pyrazine carboxamides. Further structural analysis demonstrated that the βHis48 could form a long-lasting hydrogen bond with αGlu166, which contributes to the expansion of the entrance of substrate access tunnel and accelerate substrate migration.

Aminocarbonylation of Aryl Halides to Produce Primary Amides by Using NH4HCO3 Dually as Ammonia Surrogate and Base

An efficient and clean protocol was developed for rapid production of primary aromatic amides by aminocarbonylation with NH4HCO3. Without addition of auxiliary base, the use of solid and cheap NH4HCO3 dually as ammonia surrogate and base not only promoted aminocarbonylation over subsequent dehydration and hydrolysis of amides owing to its weak basicity, and it also made the reaction manipulation clean and simplified without the presence of stinky NH3 or organic amines. The Xantphos ligand with relatively intensive π-acceptor character (1J31P–77Se=758 Hz) and wide natural bite angle (βn=111°) was found to be indispensable for the high efficiency of this reaction.

Direct synthesis of dimethyl carbonate from CO2 and methanol over CeO2 catalysts of different morphologies

The direct synthesis of dimethyl carbonate (DMC) from carbon dioxide (CO2) and methanol is an attractive approach towards conversion of the greenhouse gas - CO2 into value-added chemicals and fuels. Ceria (CeO2) catalyzes this reaction. But the conversion efficiency of CeO2 is enhanced when the byproduct water in the reaction medium is separated by employing trapping agents like 2-cyanopyridine (2-CP). In this work, the influence of morphology of CeO2 on the direct synthesis of DMC in presence of 2-CP is reported. CeO2 catalysts of cube, rod, spindle and irregular morphology (Ce - C, Ce - R, Ce - S and Ce - N, respectively) were prepared, characterized and studied as catalysts in the said reaction conducted in a batch mode. Among all, Ce - S shows superior catalytic performance with nearly 100 mol% of DMC selectivity. Catalytic activity correlates with the concentration of acid and base sites of medium strength as well as defect sites. Ce - S has an optimum number of these active sites and thereby shows superior catalytic performance. [Figure not available: see fulltext.]

Efficient and substrate-specific hydration of nitriles to amides in water by using a CeO2 catalyst

CeO2 acted as a reusable and effective catalyst for the hydration of various nitriles to amides in water under neutral conditions at low temperature (30-100 °C). CeO2 showed notable substrate specificity for nitriles that have a heteroatom adjacent to the α-carbon atom of the CN group (see scheme).

Ruthenium(III) 2-(aminofluoreneazo)phenolate complexes: Synthesis, characterization, catalytic activity in amidation reaction and Fluorescence quenching studies

A series of ruthenium(III)2-(aminofluoreneazo)phenolate complexes with general formula [RuCl(PPh3)2(L1-5)] (1–5) (L = 2-(aminofluoreneazo)phenolate ligands) have been synthesized. The characterization of the synthesized complexes was accomplished by elemental analysis, spectroscopic (FT-IR, UV–Vis, Fluorescence and EPR) and ESI-MStechniques. The catalytic performance of one of the synthesized complexes 3 for the amidation of aldehyde in the presence of NaHCO3/NH2OH·HCl has been evaluated. The fluorescence emission of complexes [RuCl(PPh3)2(L2)] (2) and [RuCl(PPh3)2(L3) (3)] are effectively quenched by 1,4-benzoquinone and 1,4-naphthoquinone in acetonitrile medium.

Metal-free one-pot domino reaction: Chemoselective synthesis of polyarylated oxazoles

A convenient method has been established for the chemoselective synthesis of polyarylated oxazoles from aromatic aldehydes and 2-cyano heteroarenes. The protocol presents a novel one-pot methodology for the synthesis of oxazole derivatives without any metal catalysts or extra oxidants. Photophysical test showed that the polyarylated oxazoles may serve as potential fluorescent materials with blue light-emitting properties.