2-aminonicotinic Acid Research Articles

Optimization of voltammetric parameters for sensitive and simultaneous determination of ferulic acid and vanillin using a glassy carbon electrode based on 2-aminonicotinic acid in the presence of surfactant media

The electrochemical sensor for simultaneous determination of ferulic acid (FA) and vanillin (VA) was prepared by electrochemical deposition of 2-aminonicotinic acid (2-ANA) on the glassy carbon (GC) electrode. The voltammetric determination of FA and VA was performed in the BR buffer solution in the presence of sodium dodecyl sulfate as a surfactant with SWV. The parameters of the SWV technique were optimized by response surface methodology experimental design. Under optimized conditions, the 2-ANA/GC modified electrode presented a linear working range of 2.8 × 10−8 M to 7.50 × 10−6 M and 7.50 × 10−6 M to 2.45 × 10−5 M for FA, 3.06 × 10−8 M to 1.27 × 10−5M for VA. The detection limit (LOD) values for FA and VA were 6.87 nM and 9.23 nM, respectively. Using the 2-ANA/GC sensor, concentrations of FA and VA in instant coffee and milk samples were determined with %recovery values between 103.40 and 97.07 and %RSD values between 0.76 and 4.40.

Synthesis and cytotoxic evaluation of some novel 3-[2-(2-phenyl-thiazol-4-yl)-ethyl]-3H-pyrido[2,3-d]pyrimidin-4-one derivatives.

Background and purpose:Pyridopyrimidine and its derivatives have a variety of chemical and biological significances. Thiazole-containing compounds have also been reported to have a wide range of biological activities. Due to the valuable cytotoxic effects of both thiazole and pyridopyrimidinone derivatives, a series of pyridopyrimidinone-thiazole hybrids were synthesized in the present study.Experimental approach:Briefly, different acyl chlorides were reacted with 2-amino nicotinic acid followed by anhydride acetic to give the corresponding pyridobenzoxazinones. The aminothiazole derivative G was also prepared via a multistep procedure and incorporated into the benzoxazinones to furnish the target pyridopyrimidinone, K1-K5. Furthermore, the cytotoxic activity of the final compounds was determined against MCF-7 and HeLa cell lines using MTT assay.Findings/Results:The results indicated that aromatic substitution on C2 of pyridopyrimidine nucleus was in favor of cytotoxic activity on both cell lines, of which, compound K5 bearing a chlorophenyl group showed the highest cytotoxicity.Conclusion and implications:The results of the present study are valuable in terms of synthesis of hybrid molecules and also cytotoxic evaluations which can be useful for future investigations about the design of novel pyridopyrimidinone-thiazole hybrids possessing better cytotoxic activities.

Two Faces of Water in the Formation and Stabilization of Multicomponent Crystals of Zwitterionic Drug-Like Compounds

Two new hydrated multicomponent crystals of zwitterionic 2-aminonicotinic acid with maleic and fumaric acids have been obtained and thoroughly characterized by a variety of experimental (X-ray analysis and terahertz Raman spectroscopy) and theoretical periodic density functional theory calculations, followed by Bader analysis of the crystalline electron density) techniques. It has been found that the Raman-active band in the region of 300 cm−1 is due to the vibrations of the intramolecular O-H...O bond in the maleate anion. The energy/enthalpy of the intermolecular hydrogen bonds was estimated by several empirical approaches. An analysis of the interaction networks reflects the structure-directing role of the water molecule in the examined multicomponent crystals. A general scheme has been proposed to explain the proton transfer between the components during the formation of multicomponent crystals in water. Water molecules were found to play the key role in this process, forming a “water wire” between the COOH group of the dicarboxylic acid and the COO– group of the zwitterion and the rendering crystal lattice of the considered multicomponent crystals.

Phototransformations of 2-aminonicotinic acid resolved with matrix isolation infrared spectroscopy and ab initio calculations

The structure and phototransformations of 2-aminonicotinic acid (ANA) induced by tunable UV laser were studied in low-temperature argon matrices with the use of Fourier-transform infrared (FTIR) spectroscopy. After the deposition of the argon matrix, two amino isomers (ANA-1 and ANA-2) were detected, with populations of 96 % and 4 %, respectively. Electronic structure calculations confirm these to be the two most stable isomers of ANA. The irradiation of the amino isomers gives rise to an intricate system of photoinduced reactions, which involves amino-imino phototautomerism, and rotations of the carboxylic group. Following irradiation at 350 nm, a rotation of the carboxylic group of ANA-1 was detected leading to increase of the ANA-2 form. In turn, at 310 nm two new imino forms (INA-1 and INA-2) of 2-aminonicotinic acid were generated indicating that UV-induced hydrogen atom transfer between ANA and INA tautomeric forms took place. The corresponding reverse photorotamerizations were also detected at 390 nm, resulting in the recovery of the initial ANA-1 and ANA-2 isomers. On the basis of electronic structure calculations, we hypothesize that ANA-INA phototautomerization takes place in the vibrationally hot electronic ground state. Its occurrence appears to be contingent on the molecule being able to access a conical intersection between the lowest singlet excited state and the ground state.

Design, Synthesis and Pharmacological Evaluation of Novel Imidazopyridine Analogues as Proton Pump Antagonist

A series of novel imidazopyridine derivatives as proton pump inhibitors was designed with compounds of CID data base and explored considering AZD0865 as standard. Many compounds were identified and docked in proton pump ATPase pocket (PDB ID: 4ux2). Molecular docking studies revealed that many compounds showed good proton pump ATPase inhibitory activity. The docking poses revealed the interaction of ligands with amino acid. The standard drug AZD0865 had docking score of -7.112302 and displayed interactions with Asn138 and Asp137. A series of novel imidazopyridine derivatives as proton pump inhibitors were docked, synthesized and characterized by IR, NMR, CHN and MS spectral analysis. The target imidazopyridines were prepared from substituted 2-aminonicotinic acid and 2-bromo-1-substituted ethanone. in vitro Studies explained that few compounds exhibited moderate to good proton pump ATPase inhibitory activity in comparison with the reference drugs i.e. AZD0865. Compounds 11 and 12 shown higher activities with the IC50 4.3. Compounds 1, 4, 6, 7, 8, 10 and 13 showed weak anti-ulcer activity with its IC50 5.2, 5.8, 5.5, 5.1, 4.9, 4.6 and 5.9 and positive control AZD0865 shown IC50 2.0.

Design and Synthesis of Novel Imidazopyridine Analogues and Evaluation as H+/K+-ATPase Antagonist

CID data base were explored considering AZD0865 as standard and docked in proton pump ATPase pocket (PDB ID: 4ux2) to find out novel imidazopyridine derivatives as proton pump inhibitors. A number of compounds showed good proton pump ATPase inhibitory activity as per the molecular docking study as compared to standard compound AZD0865. The compound AZD0865showed a docking score of -7.11 and revealed the interactions with amino acids Asn 138 and Asp 137. A series of novel imidazopyridine derivatives as proton pump inhibitors were docked, synthesized and characterized by IR, NMR, CHN and MS spectral analysis. The target imidazopyridines were prepared from the intermediate substituted 2-aminonicotinic acid and 2-bromo-1-substituted ethanone. in vitro pharmacological studies explained that some compounds exhibited moderate to good proton pump ATPase inhibitory activity in comparison with the reference drugs i.e. AZD0865. Compound N-(3-(aminomethyl)benzyl)-3-(benzylamino)-2-(o-tolyl)imidazo[1,2-a]pyridine-8-carboxamide and N-(3-(aminomethyl)benzyl)-3-(benzylamino)-2-(4-ethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide showed higher activities with the IC50 6.2 and 6.0 μg. Many compounds showed IC50 as weak antiulcer activity as compared to positive control AZD0865.

Impact of 2-Aminonicotinic Acid and/or β-Cyclodextrin on the Morphology of Metal Carbonates (M = Ca2+ and Sr2+) Crystallization

We examined the crystallization impact of the surfactant, 2-aminonicotinic acid and/or β-cyclodextrin on the formation of two anhydrous metal carbonates, MCO3 (M = Ca2+ and Sr2+), from their respective calcium chloride and strontium chloride salts along with NaHCO3 at room temperature. By varying the concentrations of this hybrid surfactant to the concentrations of MCO3 during the preparations and examined their particle sizes by PXRD, FTIR, TGA and SEM. The characterization on these newly formed anhydrous metal carbonates clearly indicated that CaCO3 formed with three different shapes such as truncated calcite, hexagonal calcite and rod shaped aragonite. Whereas, SrCO3 formed with two different shapes such as hexagonal poles and bloom scale bars by varying concentrations of the surfactants. The mixed surfactant certainly made an impact on the metal carbonates formations with different shapes and sizes by varying surfactants concentrations and conditions.

Syntheses and single crystal X-ray diffraction analysis of five isostructural 2D MOCCs

Five two-dimensional metal–organic coordination compounds (MOCCs) have been solvothermally synthesized by the combination of 2-aminonicotinic acid (ANA) and transition metal ions, viz. Co(II), Ni(II), Cu(II), Zn(II) and Cd(II), in water–ethanol mixed solvent. They are formulated as [Co(C6H5N2O2)2], (Co–ANA); [Ni(C6H5N2O2)2], (Ni–ANA) [Cu(C6H5N2O2)2], (Cu–ANA), [Zn(C6H5N2O2)2], (Zn–ANA) and [Cd(C6H5N2O2)2], (Cd–ANA). Single crystal X-ray diffraction studies for the complexes Co–ANA, Ni–ANA and Cd–ANA have also been carried out. These three complexes crystallize in the tetragonal crystal system with the space group P41212. The metal ions in all these complexes have an octahedral coordination environment. The six coordinations are satisfied by two pyridine N-atoms from two different ANA ligands and four oxygen atoms from two chelating carboxylate groups of another two ANA ligands. The topological motif of the coordination network is defined as 2-periodic net or square lattice (sql). These complexes were further characterized by elemental, FT-IR spectral, thermal and powder X-ray diffraction analyses.

Imidoyl Radicals for the Synthesis of Chromenoquinolines and Naphthyridines

The stability of imidoyl radicals prepared from 2-(2-alkenyloxy)-phenyl selenoimidates and 2-(2-allylamino)-phenyl selenoimidates and their intramolecular free radical cyclization through the slow addition of tri-N-butyltin hydride and AIBN to obtain 4-chromanones and 4-quinolones were studied. The extension of the methodology to N-phenyl substituted imidoyl selenoates produced tandem cyclizations of the imidoyl radical with the allyl substituent, followed for a second cyclization of the intermediate radical with the aromatic substituent to produce dihydro-chromenoquinolines or tetrahy-dro-dibenzonaphtyridines. Further oxidation with DDQ produced: 6H-chromeno [4,3,b] quinoline and 7-methyl-6H-chromenoquinoline from 2-alkenylamino-phenylbenzamide and 5,6-dihydro-dibenzo [b,h][1,6] naphthyridine and 5,6-dihydro-7-methyl-dibenzo [b,h][1,6] naphthyridine from 2-2-(alkylamino)-N-phenylbenzamides. The cyclization of 2-(N,N-di-prop-2.enylamino)-N-phenylnicotinamide selenoate obtained from 2-aminonicotinic acid, produced 5,6-dihidro-benzo[b]pyrido2,3-h] [1,6] naphthyridine.

Hydrogen Peroxide Insular Dodecameric and Pentameric Clusters in Peroxosolvate Structures.

Peroxosolvates of 2-aminonicotinic acid (I) and lidocaine N-oxide (II) including the largest insular hydrogen peroxide clusters were isolated and their crystal structures were determined by single-crystal X-ray diffraction. An unprecedented dodecameric hydrogen peroxide insular cluster was found in I. An unusual cross-like pentameric cluster was observed in the structure of II. The topology of the (H2 O2 )12 assembly was never observed for small-molecule clusters. In I and II new double and triple cross-orientational disorders of H2 O2 were found. Cluster II is the first example of a peroxosolvate crystal structure containing H2 O2 molecules with a homoleptic hydrogen peroxide environment. In II, a hydrogen bond between an H2 O2 molecule and a peptide group -CONH⋅⋅⋅O2 H2 was observed for the first time.

Synthesis, spectral studies and biological evaluation of 2-aminonicotinic acid metal complexes

We synthesized 2-aminonicotinic acid (2-ANA) complexes with metals such as Co(II), Fe(III), Ni(II), Mn(II), Zn(II), Ag(I),Cr(III), Cd(II) and Cu(II) in aqueous media. The complexes were characterized and elucidated using FT-IR, UV–Vis, a fluorescence spectrophotometer and thermo gravimetric analysis (TGA). TGA data showed that the stoichiometry of complexes was 1:2 metal/ligand except for Ag(I) and Mn(II) where the ratio was 1:1. The metal complexes showed varied antibacterial, fungicidal and nematicidal activities. The silver and zinc complexes showed highest activity against Bacillus subtilis and Bacillus licheniformis respectively. Fusarium oxysporum was highly susceptible to nickel and copper complexes whereas Macrophomina phaseolina was completely inert to the complexes. The silver and cadmium complexes were effective against the root-knot nematode Meloidogyne javanica.

Photocatalytic activity of CuO nanoparticles incorporated in mesoporous structure prepared from bis(2-aminonicotinato) copper(II) microflakes

An easy method for preparing CuO nanoparticles incorporated in a mesoporous structure was presented based on the thermal decomposition of a copper complex. The novel copper coordination compound of [Cu(anic)2]·0.75H2O (anic= 2-aminonicotinate) with the microflake morphology was synthesized through the reaction of 2-aminonicotinic acid (Hanic) and copper(II) nitrate. Using elemental analysis and Fourier transform infrared (FTIR) spectroscopy, the chemical composition of CuC12H11.5N4O4.75 was proposed. Calcination process at 550 °C for 4 h transformed the microflakes into CuO nanoparticles incorporated in a mesoporous structure. The FTIR peaks assigned to 2-aminonicotinate were completely removed after calcination, confirming CuO formation. X-ray diffraction (XRD) analysis also confirmed the generation of pure and crystalline CuO. SEM showed CuO nanoparticles with the average diameter of 75 nm. The diffuse reflectance spectrum (DRS) of the CuO nanoparticles showed a band gap energy of −1.58 eV. The degradation efficiency toward rhodamine B was almost 100 % after 5 h illumination when both CuO and H2O2 were utilized. The results show that the product can be used as an efficient photocatalyst for water treatment.

SYNTHESIS AND NMR SPECTRAL CHARACTERIZATION OF NOVEL 2,3-POLYMETHYLENEPYRIDO[2,3-D]PYRIMIDIN-4-ONES

We have synthesized of novel 2,3-polymethylenepyrido[2,3-d]pyrimidin-4-ones via condensation of the 2-aminonicotinic acid together with lactams in the presence of phosphorus oxychloride. The structures of the newly synthesized pyrido[2,3-d]pyrimidines were confirmed by 1H and 13c NMR spectral data.

Photocatalytic activity of mesoporous microbricks of ZnO nanoparticles prepared by the thermal decomposition of bis(2-aminonicotinato) zinc (II)

Hollow microblocks of [Zn(anic)2], as a novel coordination compound, were synthesized using 2-aminonicotinic acid (Hanic) and zinc (II) nitrate tetrahydrate. The chemical composition of the zinc complex, ZnC12H10N4O4, was determined by Fourier transform infrared (FTIR) spectroscopy and elemental analysis. The synthesized zinc complex was used as a precursor to produce ZnO nanostructures by calcination at 550 °C for 4 h. Morphological studies by scanning electron microscopy and transmission electron microscopy revealed the formation of porous microbricks of ZnO nanoparticles. N2 adsorption-desorption analysis showed that the obtained ZnO microbricks possess a mesoporous structure with a surface area of 8.13 m2/g and a pore size of 22.6 nm. The X-ray diffraction pattern of the final product proved the formation of a pure ZnO composition with a hexagonal structure. Moreover, FTIR analyses showed that the 2-aminonicotinic acid ligand peaks were absent after the calcination step. Diffuse reflectance spectroscopy was used to determine the band gap energy of the produced ZnO and it was about 3.19 eV. To investigate the photocatalytic activity of the porous ZnO nanostructure, a series of photocatalytic tests were carried out to remove Congo red, as a representative toxic azo dye, from aqueous solution. The results show that the product can be used as an efficient photocatalyst for waste water treatment with high degradation efficiency.

Protonated 2-Aminonicotinic Acid as Charge Complement in POM-Based Inorganic–Organic Hybrids: Synthesis, Crystal Structure and Characterization

Two supramolecular compounds, (2-HANA)4(SiW12O40)·12H2O (1) and (H3O)(2-HANA)2(HPW12O40)·11H2O (2), ANA = 2-aminonicotinic acid, were synthesized in conventional method in aqueous solution and characterized with elemental analysis, IR spectrography, thermal analysis. Their crystal structures were determined with X-ray single-crystal diffraction and CV behavior were examined. In the compounds ANA is protonated and acts as charge complement and hydrogen bond donor and acceptor. In 1 there is a supramolecular chain formed through fourfold hydrogen bonds between water molecules and SiW12 anions, and in 2 a supramolecular layer is formed by hydrogen bonds between protonated O1W molecules and PW12 anions. The protonated water molecule is identified from IR spectrum of 2.

2-Aminonicotinic Acid 1-Oxides Are Chemically Stable Inhibitors of Quinolinic Acid Synthesis in the Mammalian Brain: A Step toward New Antiexcitotoxic Agents

3-Hydroxyanthranilic acid 3,4-dioxygenase (3-HAO) is the enzyme responsible for the production of the neurotoxic tryptophan metabolite quinolinic acid (QUIN). Elevated brain levels of QUIN are observed in several neurodegenerative diseases, but pharmacological investigation on its role in the pathogenesis of these conditions is difficult because only one class of substrate-analogue 3-HAO inhibitors, with poor chemical stability, has been reported so far. Here we describe the design, synthesis, and biological evaluation of a novel class of chemically stable inhibitors based on the 2-aminonicotinic acid 1-oxide nucleus. After the preliminary in vitro evaluation of newly synthesized compounds using brain tissue homogenate, we selected the most active inhibitor and showed its ability to acutely reduce the production of QUIN in the rat brain in vivo. These findings provide a novel pharmacological tool for the study of the mechanisms underlying the onset and propagation of neurodegenerative diseases.

2 - Aminonikotinik Asit ’in 131 I ile Radyo i şaretlenmesi ve Albino Sıçanlarda Biyodağılımının Yapılması

Turk In this study, labeling of 2-aminonicotinic acid (2-ANA) with 131I, radiolabeling efficiency, the effect of pH and oxidizing agent on the labeling yield, in vitro stability and biodistribution of radiolabelling substance were made. Electrophoresis and Radio Thin Layer Chromatography (RTLC) methods were used in the quality control study of radiolabeled substance (131I-2-ANA). Biodistribution studies were done in nine male Albino Wistar rats which were categorized 3 groups. The rats were sacrificed at various time intervals (15, 60 and 180 min), their organs were removed, and percentage of injected dose per gram (% ID/g) was calculated. The labeling yield of 2-ANA was determined as % 86.41±3.11. Maximum uptake of 131I-2-ANA was seen in the stomach, kidneys, pancreas, liver, thyroid small intestine and fat. We concluded that the binding efficiency of 131I-2-ANA was high and it had sufficient stability for diagnostic studies. © Afyon Kocatepe Universitesi 1.Giris Insanlardaki bulasici veya bulasici olamayan hastaliklarin belirlenmesi (tumor, iltihap, vb) klinik uygulamalarda buyuk bir sorun olarak devam etmektedir (Boerman et al., 2001; Rennen et al., 2001). incelemelerle ortaya cikarilmaktadir (Cindas et al., 2001; De Bois et al., 1996). Sintigrafik calismalar ise genelde radyofarmasotiklerle yapilmaktadir. Bu tur yerlerin tanisi icin kullanilan radyofarmasotiklerin

Sonochemical Synthesis of Nano-structured Lead(II) Coordination Polymer with 2-Aminonicotinic Acid: Thermal, Structural and X-ray Powder Diffraction Studies

A new one-dimensional crystalline and nano-structured Pb(II) coordination polymer, [Pb(2-anc)2(NO3)2] n (1) {2-Hanc = 2-aminonicotinic acid}, were synthesized via heat gradient and sonochemical methods. The new produced nano-structure was characterized by scanning electron microscopy, X-ray powder diffraction, IR spectroscopy, and elemental analyses. Structural characterization by single crystal X-ray diffraction exhibits two-dimensional polymeric units for compound 1. Thermal stability of nano and bulk samples of compound 1 were studied and compared. PbO nano-particles was then obtained via calcination of nano-compound 1 at high and low temperatures. The calcinations result demonstrates that compound 1 may be suitable precursor for the preparation of nanoscale lead(II) oxide without need for special conditions like high temperature, long times and pressure control.

An efficient and convenient method for synthesizing new derivatives of pyrido[2,3-e]pyrrolo[1,2-a][1,4]diazepine-5,10-dione via Sonogashira, Suzuki–Miyaura, and Stille cross-coupling reactions

An efficient method for synthesizing new pyrido[2,3-e]pyrrolo[1,2-a][1,4]diazepine-5,10-dione derivatives starting from l-proline methyl ester and 2-aminonicotinic acid is presented. This method employs Pd-catalyzed cross-coupling reaction on the corresponding brominated compound 4 (key intermediate). Sonogashira, Stille, and Suzuki–Miyaura cross-coupling reactions are used to generate products 5a–g, 6, 7a–c, and 8a–e, in good to excellent yields.

Molecular structure (monomeric and dimeric structure) and HOMO–LUMO analysis of 2-aminonicotinic acid: A comparison of calculated spectroscopic properties with FT-IR and UV–vis

The experimental (UV–vis and FT-IR) and theoretical study of 2-aminonicotinic acid (C6H6N2O2) was presented in this work. The ultraviolet absorption spectrum of title molecule that dissolved in ethanol and water were examined in the range of 200–400nm. The FT-IR spectrum of the title molecule in the solid state were recorded in the region of 400–4000cm−1. The geometrical parameters and energies of 2-aminonicotinic acid have been obtained for all four conformers/isomers (C1, C2, C3, C4) from DFT (B3LYP) with 6-311++G(d,p) basis set calculations. C1 form has been identified the most stable conformer due to computational results. Therefore, spectroscopic properties have been searched for the most stable form of the molecule. The vibrational frequencies were calculated and scaled values were compared with experimental FT-IR spectrum. The complete assignments were performed based on the total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanics (SQM) method. Also the molecular structures, vibrational frequencies, infrared intensities were calculated for a pair of molecules linked by the intermolecular OH⋯O hydrogen bond. Moreover, the thermodynamic properties of the studied compound at different temperatures were calculated. Besides, charge transfer occurring in the molecule between HOMO and LUMO energies, frontier energy gap, molecular electrostatic potential (MEP) were calculated and presented. The spectroscopic and theoretical results are compared to the corresponding properties for monomer and dimer of C1 conformer. The optimized bond lengths, bond angles, calculated frequencies and electronic transitions showed the agreement with the experimental results.