Category: 27828-71-3

Computed Properties of C6H5NO3. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5-Hydroxynicotinic acid, is researched, Molecular C6H5NO3, CAS is 27828-71-3, about From 5-hydroxynicotinic acid to nitrogenous (4 + 3)-cycloadducts. Author is Harmata, Alexander S.; Harmata, Michael.

The detailed three-step preparation of azabicyclo[4.3.1]decadienone I from 5-hydroxynicotinic acid, via a [4+3]-cycloaddition of a N-alkyl oxidopyridinium salt with a diene, was reported. Extension of the methodol. leading to other [4+3]-cycloaddition adducts was also discussed.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Hydroxynicotinic acid, is researched, Molecular C6H5NO3, CAS is 27828-71-3, about Selectivity of substrate binding and ionization of 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase, the main research direction is substrate methylhydroxypyridine carboxylate oxygenase kinetics active site; 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase; flavin-dependent monooxygenase; hydroxylase; oxidative cleavage; oxygenase.Application In Synthesis of 5-Hydroxynicotinic acid.

2-Methyl-3-hydroxypyridine-5-carboxylic acid (MHPC) oxygenase (EC 1.14.12.4) from Pseudomonas sp. MA-1 is a flavin-dependent monooxygenase that catalyzes a hydroxylation and aromatic ring cleavage reaction. The functional roles of two residues, Tyr223 and Tyr82, located ∼ 5 Å away from MHPC, were characterized using site-directed mutagenesis, along with ligand binding, product anal. and transient kinetic experiments Mutation of Tyr223 resulted in enzyme variants that were impaired in their hydroxylation activity and had Kd values for substrate binding 5-10-fold greater than the wild-type enzyme. Because this residue is adjacent to the water mol. that is located next to the 3-hydroxy group of MHPC, the results indicate that the interaction between Tyr223, H2O and the 3-hydroxyl group of MHPC are important for substrate binding and hydroxylation. By contrast, the Kd for substrate binding of Tyr82His and Tyr82Phe variants were similar to that of the wild-type enzyme. However, only ∼ 40-50% of the substrate was hydroxylated in the reactions of both variants, whereas most of the substrate was hydroxylated in the wild-type enzyme reaction. In free solution, MHPC or 5-hydroxynicotinic acid exists in a mixture of monoanionic and tripolar ionic forms, whereas only the tripolar ionic form binds to the wild-type enzyme. The binding of tripolar ionic MHPC would allow efficient hydroxylation through an electrophilic aromatic substitution mechanism. For the Tyr82His and Tyr82Phe variants, both forms of substrates can bind to the enzymes, indicating that the mutation at Tyr82 abolished the selectivity of the enzyme towards the tripolar ionic form. Transient kinetic studies indicated that the hydroxylation rate constants of both Tyr82 variants are approx. two- to 2.5-fold higher than that of the wild-type enzyme. Altogether, our findings suggest that Tyr82 is important for the binding selectivity of MHPC oxygenase towards the tripolar ionic species, whereas the interaction between Tyr223 and the substrate is important for ensuring hydroxylation. These results highlight how the active site of a flavoenzyme is able to deal with the presence of multiple forms of a substrate in solution and ensure efficient hydroxylation.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 27828-71-3, is researched, Molecular C6H5NO3, about Acid-base reactions of β-hydroxypyridinecarboxylic acids, the main research direction is pyridinecarboxylate hydroxy ionization protonation; ionization hydroxypyridinecarboxylate; protonation hydroxypyridinecarboxylate; tautomerism hydroxypyridinecarboxylate.Application of 27828-71-3.

The protonation and ionization constants of 5-hydroxynicotinic and -picolinic and 3-hydroxyisonicotinic acids and their Et esters were determined In strongly acidic media these acids are protonated; as the pH is increased, they exist 1st as the bipolar ions (e.g., I), then as tautomeric monoanions, and finally as the dianions. The pH limits of these forms were determined for the 3 acids.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 5-Hydroxynicotinic acid, is researched, Molecular C6H5NO3, CAS is 27828-71-3, about NMR study of acid-base reactions of 3-hydroxypyridine, 3-hydroxypyridine N-oxide, and β-hydroxypyridinecarboxylic acids.Quality Control of 5-Hydroxynicotinic acid.

An NMR method was used to determine the protonation and ionization constants of 3-hydroxypyridine (I) and its N-oxide (II); 5-hydroxynicotinic acid, 3-hydroxyisonicotinic acid (III), and their Et esters; and 5-hydroxypicolinic acid. Introduction of the CO2H group at different positions of the β-hydroxypyridine ring generally had a deshielding effect on the ring protons. The ionization of the CO2H group in nicotinic and picolinic acid was not appreciably affected by introduction of the OH group. Ionization of III was hindered by intramol. H bonding between the OH and CO2H groups. The acidity of II was much greater than that of I.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 27828-71-3, is researched, SMILESS is O=C(O)C1=CN=CC(O)=C1, Molecular C6H5NO3Journal, Article, Biochimica et Biophysica Acta, General Subjects called Uptake and metabolism of nicotinic acid by human blood platelets. Effects of structure analogs and metabolic inhibitors, Author is Gaut, Zane N.; Solomon, Harvey M., the main research direction is nicotinate metabolism platelet; metabolism nicotinate platelet; platelet nicotinate metabolism; uptake nicotinate platelet.Related Products of 27828-71-3.

Human platelets incubated for 1 hr at 37° with nicotinic acid-7-14C (10 micromoles) accumulated the radioactivity with a gradient, (dpm per ml intraplatelet water)/(dpm per ml incubation medium), of approx. 20. The uptake process involved incorporation of the isotope into compounds such as NAD which do not readily diffuse from the cell. Of the total radioactivity inside, nicotinic acid represented approx. 3.9%, nicotinamide, 2.6%; NAD, 17.7%; and other products, 75.8%. Such synthesis and accumulation of radioactivity was variously inhibited by a number of analogs of nicotinic acid as well as by dinitrophenol, NaF, salicylate, and NaCN. Of the analogs studied, 2-hydroxynicotinic acid was the most potent. It reduced the gradient of radioactivity to 1.4 at 1mM and inhibited isotopic incorporation into the compounds previously described. These data suggest that 2-hydroxynicotinic acid inhibits one or more of the early reactions in the biosynthesis of NAD and nicotinamide. Nicotinamide-7-14C was neither accumulated nor metabolized by the platelet.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Product Details of 27828-71-3. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 5-Hydroxynicotinic acid, is researched, Molecular C6H5NO3, CAS is 27828-71-3, about Construction of a novel 2D Pb(II)-Organic framework: Syntheses, crystal structure, and property. Author is Jin, Feng.

Metal-organic frameworks (MOFs) have been widely explored and investigated as inorganic-organic hybrid materials for lots of scientists, which is not only due to their broad applications but also their various structures. Herein, a novel 2D Pb(II)-organic framework (complex 1) was successfully synthesized by heating 5-hydroxynicotinic acid (HL) and Pb(NO3)2 in a mixed solution of MeCN and H2O. The as-synthesized sample was measured by various characterization analyses, including elemental anal. of C, H, and N, single-crystal x-ray diffraction, powder x-ray diffraction, scanning electron microscope, and thermal gravimetric anal. More importantly, complex 1 can be considered as a high-efficient luminescent sensor for Fe3+ with good recyclability and high selectivity. And the Ksv value of complex 1 to Fe3+ was calculated to be ∼4.7 x 103 M-1. Thanks to the stability and Pb(II) centers as Lewis acid sites, complex 1 has a potential application as a heterogeneous catalyst for the CO2 cycloaddition reaction with preferable recyclability.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

HPLC of Formula: 27828-71-3. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 5-Hydroxynicotinic acid, is researched, Molecular C6H5NO3, CAS is 27828-71-3, about β-Hydroxypyridinecarboxylic acids. Communication 1. Electrophilic reactions of 5-hydroxynicotinic acids.

5-Hydroxynicotinic acid derivatives (I, R1 = H, iodo, piperidinomethyl, morpholinomethyl, NO2, PhN:N, p-BrC6H4N:N, p-O2NC6H4N:N, p-MeOC6H4N:N, R2 = H; R1 = H, iodo, PhN:N, NO2, morpholinomethyl, R2 = Et) were obtained in 20-98% yields by appropriate electrophilic substitution reactions of I (R1 = H, R2 = H, Et).

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Danilenko, Lyudmila M.; Pokrovskii, Michail V.; Kesarev, Oleg G.; Timokhina, Alyona S.; Sernov, Lev N. published an article about the compound: 5-Hydroxynicotinic acid( cas:27828-71-3,SMILESS:O=C(O)C1=CN=CC(O)=C1 ).Computed Properties of C6H5NO3. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:27828-71-3) through the article.

The search for new compounds with cardioprotective activity among the derivatives of 5-hydroxynicotinic acid is promising. The objective of this study is to study the cardioprotective effects of the derivatives from 5-hydroxynicotinic acid SSC-77 (K-5-hydroxynicotinic acid) and SSC-497 (Mg-5-hydroxynicotinica acid). The cardioprotective effect of SSC-77 and SSC-prisocorubicin (20 mg/kg, i.p. for 48 h) pathol. was assessed by the results of the functional test with high-frequency stimulation (480 bpm). The research of myocardial resistance to ischemia/reperfusion injury was studied according to hypo-reperfusion model on an isolated rat heart on the record of pressure in the left ventricle. The isoenzyme creatine phosphokinase (KFK-MB) and lactate dehydrogenase (LDH) were determined for the complex evaluation of myocardial damage in the flowing off perfusate from isolated hearts. The activity of lipid peroxidation (LPO) was assessed by the content of malondialdehyde (MDA) and diene conjugates (DC). SSC-77 (27.6 mg/kg/day) and SSC-497 (58.1 mg/kg/day) show a cardioprotective effect using the doxorubicin pathol. model, which is expressed in the decrease of diastolic dysfunction coefficient (StTTI) to 2.1 ± 0.2 r.u. and 3.3 ± 0.1 r. units, resp., as compared with the control group 8.3 ± 0.1 r. un. Using the model of hypo-reperfusion, the substances SSC-77 (10-6 mol/l) and SSC-497 (10-6 mol/l) prevent the decrease of contractility indexes on the 5th and 20th min during the reperfusion period in comparison with the control where the fall made 50%. The cardioprotective effect was confirmed by 47% and 39% decrease concerning the levels of KFK-MB marker damage by 39% and 47% and LDH by 21.8% and 19.6%, resp., in the series with SSC-77 and SSC-497 in comparison with the control group, as well as by the prevention of LPO products MDA and DC accumulation in the ventricular myocardium. The derivatives of 5-hydroxynicotinic acid SSC-77 and SSC-497 reduce diastolic dysfunction, prevent the decrease of cardiac functional activity after ischemia/reperfusion, reduce the irreversible damage of cardiomyocytes, and have antioxidant properties.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《5-Chloro- and 5,6-dichloronicotinic acids》. Authors are Graf, Roderich; Lederer-Ponzer, Ernst; Kopetz, Viktor; Purkert, Renato; Laszlo, Paul.The article about the compound:5-Hydroxynicotinic acidcas:27828-71-3,SMILESS:O=C(O)C1=CN=CC(O)=C1).Recommanded Product: 5-Hydroxynicotinic acid. Through the article, more information about this compound (cas:27828-71-3) is conveyed.

Nicotinic acid HCl salt (100 g.) and 180 g. SOCl2, gently boiled 5 days and then heated in tubes 12 hrs. at 180°, give 50-60% of a mixture of the 5-Cl and 5,6-di-Cl derivatives (I), in about equal amounts; more SOCl2 increases the proportion of the di-Cl acid. 5-Aminopyridine-3-carboxylic acid (II), m. 288-90° (decomposition). II through the diazo reaction gives the 5-Br derivative, m. 182-3°; chloride, m. 74-5°; Me ester, m. 98-9°; Ph ester, m. 86-7°. The chloride and N2H4.H2O in C6H6 give sym-bis(5-bromo-3-pyridoyl)hydrazine, m. 308° (decomposition). The Me ester gives 5-bromopyridine-3-carbonyl hydrazide, m. 193-4° (benzal derivative, m. 191-3°); the azide m. 88-9° (decomposition) and with absolute EtOH gives 5-bromo-3-carbethoxyaminopyridine, m. 150-1°; Me ester, m. 169-70°; heating the Et ester with 30% NaOH gives 5-bromo-3-aminopyridine (III), b12 149-50°, m. 66-7°; the intermediate Na 5-bromo-3-pyridylcarbamate was also analyzed; Ac derivative of III, m. 127-8° (dihydrate, m. 76-8°); picrate of III, deep yellow, m. 212-3°; chloroaurate, red-orange, m. 185-7°. 5-Iodopyridine-3-carboxylic acid, m. 220°; Ph ester, m. 100-1° Me ester, m. 121°; Et ester, m. 86-7°; amide, m. 221-2°. 5-Hydroxypyridine-3-carboxylic acid, m. 299° (decomposition). The Et ester of I and N2H4.H2O give Et 5-chloro-6-hydrazinopyridine-3-carboxylate (IV), m. 137-8°; the hydrazide, gray, m. 238-40°; the free acid m. 248-9° and was also obtained directly from I. IV on diazotizing yields Et 5-chlorobenzotetrazole-3-carboxylate, m. 95-6°; the free acid m. 195-6°; heating with HCO2H gives 5-chlorobenzotriazole-3-carboxylic acid, m. above 300°. I and concentrated NH4OH at 180-90° give 6-amino-5-chloropyridine-3-carboxylic acid, m. 323° (decomposition); Me ester, m. 163-5°; the Me ester of the 6-HO derivative m. 218°.

If you want to learn more about this compound(5-Hydroxynicotinic acid)Recommanded Product: 5-Hydroxynicotinic acid, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(27828-71-3).

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Substituted on the Nicotinic Acid and Adenine Ribosides. Effects on Receptor Mediated Ca2+ Release》. Authors are Trabbic, Christopher J.; Zhang, Fan; Walseth, Timothy F.; Slama, James T..The article about the compound:5-Hydroxynicotinic acidcas:27828-71-3,SMILESS:O=C(O)C1=CN=CC(O)=C1).COA of Formula: C6H5NO3. Through the article, more information about this compound (cas:27828-71-3) is conveyed.

Nicotinic acid adenine dinucleotide phosphate (NAADP) is a Ca2+ releasing intracellular second messenger in both mammals and echinoderms. The authors report that large functionalized substituents introduced at the nicotinic acid 5-position are recognized by the sea urchin receptor, albeit with a 20-500-fold loss in agonist potency. 5-(3-Azidopropyl)-NAADP was shown to release Ca2+ with an EC50 of 31 μM and to compete with NAADP for receptor binding with an IC50 of 56 nM. Attachment of charged groups to the nicotinic acid of NAADP is associated with loss of activity, suggesting that the nicotinate riboside moiety is recognized as a neutral zwitterion. Substituents (Br and N3) can be introduced at the 8-adenosyl position of NAADP while preserving high potency and agonist efficacy and an NAADP derivative substituted at both the 5-position of the nicotinic acid and at the 8-adenosyl position was also recognized although the agonist potency was significantly reduced.

There is still a lot of research devoted to this compound(SMILES：O=C(O)C1=CN=CC(O)=C1)COA of Formula: C6H5NO3, and with the development of science, more effects of this compound(27828-71-3) can be discovered.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method