Anthranilic Acid Research Articles

Advances in the Synthesis of Heterocycles with Two and Three Heteroatoms using Hydrazonoyl Halides

AbstractThe review covers the results of studies published in the literature on the use of hydrazonoyl halides in the synthesis of five‐ (pyrazoles, thiazoles, triazoles, oxa‐ and thiadiazoles), six‐ (oxa‐ and thiadiazines, indazoles, pyridazines, pyrazines, tetrazines) or seven‐membered (benzotriazepine) heterocycles. In the formation of these heterocycles, the main intermediate stage of the reaction is the in situ generation of nitrilimine, which enters into a cycloaddition reaction with substituted acetylenes (including in situ generated benzynes, naphthynes), allenes, activated olefins, anthranilic acid derivatives, organosulfur compounds (mercaptoaldehydes, mercaptocarboxylic acids) or with fused heterocycles. Examples are given of the formation of heterocycles by replacing the halogen atom from a hydrazonoyl halide molecule with a nucleophilic group, followed by exhaustive intramolecular cyclization into the target compound. There are discussions of reactions in which the cycloaddition of the nitrilimine to the in situ synthesized Knoevenagel condensation product (from CH‐acid compounds, such as di‐ and monocarbonyl compounds, dinitrile malonic acid) occurs, leading to spiro‐linked or conventional pyrazoles. Some syntheses of biologically active representatives are shown.

Anthranilic Acid: A Versatile Monomer for the Design of Functional Conducting Polymer Composites

Polyaniline has been utilized in various applications, yet its widespread adoption has often been impeded by challenges. Composite systems have been proposed as a means of mitigating some of these limitations, and anthranilic acid (2-aminobenzoic acid) has emerged as a possible moderator for use in co-polymer systems. It offers improved solubility and retention of electroactivity in neutral and alkaline media, and, significantly, it can also bestow chemical functionality through its carboxylic acid substituent, which can greatly ease post-polymer modification. The benefits of using anthranilic acid (as a homopolymer or copolymer) have been demonstrated in applications including corrosion protection, memory devices, photovoltaics, and biosensors. Moreover, this polymer has been used as a versatile framework for the sequestration of metal ions for water treatment, and, critically, these same mechanisms serve as a facile route for the production of catalytic metallic nanoparticles. However, the widespread adoption of polyanthranilic acid has been limited, and the aim of the present narrative review is to revisit the early promise of anthranilic acid and assess its potential future use within modern smart materials. A critical evaluation of its properties is presented, and its versatility as both a monomer and a polymer across a spectrum of applications is highlighted.

New phenols and one aminobenzoic acid derivative isolated from the roots of Rhus chinensis Mill.

Four new phenols and one new aminobenzoic acid derivative, with five known phenols were isolated from the roots of Rhus chinensis Mill. Their structures were elucidated by UV, IR, HRESIMS, 1D and 2D NMR spectra, as well as optical rotations. Compound 4 significantly inhibited mouse ear inflammation (inhibitory rate of 44.03%), and significantly extended the time of pain response (extension rate of 48.55%), showing significant anti-inflammatory and analgesic effects in vivo.

The role of the kynurenine pathway in cardiovascular disease.

The kynurenine pathway (KP) serves as the primary route for tryptophan metabolism in most mammalian organisms, with its downstream metabolites actively involved in various physiological and pathological processes. Indoleamine 2,3-dioxygenase (IDO) and tryptophan 2,3-dioxygenase (TDO) serve as the initial and pivotal enzymes of the KP, with IDO playing important and intricate roles in cardiovascular diseases. Multiple metabolites of KP have been observed to exhibit elevated concentrations in plasma across various cardiovascular diseases, such as atherosclerosis, hypertension, and acute myocardial infarction. Multiple studies have indicated that kynurenine (KYN) may serve as a potential biomarker for several adverse cardiovascular events. Furthermore, Kynurenine and its downstream metabolites have complex roles in inflammation, exhibiting both inhibitory and stimulatory effects on inflammatory responses under different conditions. In atherosclerosis, upregulation of IDO stimulates KYN production, mediating aromatic hydrocarbon receptor (AhR)-induced exacerbation of vascular inflammation and promotion of foam cell formation. Conversely, in arterial calcification, this mediation alleviates osteogenic differentiation of vascular smooth muscle cells. Additionally, in cardiac remodeling, KYN-mediated AhR activation exacerbates pathological left ventricular hypertrophy and fibrosis. Interventions targeting components of the KP, such as IDO inhibitors, 3-hydroxyanthranilic acid, and anthranilic acid, demonstrate cardiovascular protective effects. This review outlines the mechanistic roles of KP in coronary atherosclerosis, arterial calcification, and myocardial diseases, highlighting the potential diagnostic, prognostic, and therapeutic value of KP in cardiovascular diseases, thus providing novel insights for the development and application of related drugs in future research.

Comparative Phytochemistry of Vitellaria paradoxa: Towards Establishing a Chemotaxonomic Marker

Plants have been known to serve as source of food, income and in the maintenance of health, with their phytochemicals responsible for the biological properties of plants. All parts of shea tree (Vitellaria paradoxa) are consumed by human and livestock as medicine. The variations in the morphology and chemistry of shea tree and its product have been attributed to the various factors including their geographical sources among others. The phytochemical study of methanol extracts of the stem and leaf of shea tree collected from three locations were determined and compared. Qualitative phytochemical analysis indicated the presence of carbohydrates, cardiac glycosides, tannins, saponins, steroids, flavonoids, alkaloids and triterpenes. Alkaloidal contents in the leaf extracts ranged from 8.96 ± 0.05 to 16.96 ± 0.48 while the content in the stem extracts is 5.38 ± 0.04 to 14.93 ± 0.02. The phenol contents were higher in both extracts ranging from 43.05 ± 0.04 to 142.96 ± 0.07 and 85.05 ± 0.04 to 148.51 ± 0.07 in the leaf and stem extracts, respectively. Saponin contents in the leaf range from 3.56 ± 0.01 to 19.46 ± 0.01 in the leaf extracts and 9.93 ± 0.01 to 16.62 ± 0.01 in the stem extracts. Compounds such as myricetin, kaempferol-3-glucuronide, dihydroisorhamnetin, vanillic acid, 5,7-dihydroxy2-(4-hydroxy-3)methoxy)-3-{(3,4,5- trihydroxy-6 (hydroxymethyl)-oxan-2-yl)oxy}-4H-chromen4-one, 1H-indole-3-acetronitrille, 3,5-trihydroxy-10 methylacridone, syringin, gallic acid, anthranilic acid and quassin were identified in the liquid chromatography-mass spectroscopies (LC-MS) of the methanolic stem and leaf extracts of shea tree. The results of the phytochemical investigation indicate variation in the chemical composition of the plant across the study area.

A stability-indicating HPLC assay of ten different vitamins in a food supplement: Appraisal of the method's greenness, whiteness, and blueness

Due to their susceptibility to degradation, vitamin levels in food formulations may differ from those found in the finished product. Vitamin levels can be impacted by processing and storage. In this work, the ingredients of Strong B50 ® film-coated tablets were estimated simultaneously using simple efficient stability indicating HPLC method. Strong B50 ® film-coated tablets contain thiamine (VB1), riboflavin (VB2), calcium pantothenate (VB5), pyridoxine (VB6), vitamin C (VC), folic acid (FA), biotin (BT), inositol (IS), niacin (NC), para-aminobenzoic acid (PB), cyanocobalamine (B12), choline bitartarate, and iron gluconate. Hypersil BDS C18 column was used for achieving reasonable separation. Mobile phases (A) and (B) were utilized, the mobile phase (A) consisted of 0.015 M Hexane sulfonic acid sodium salt + 0.1 % Triethylamine and orthophosphoric acid was used to adjust the pH to (2.9) while (B) system consisted of acetonitrile. Validation of the method was assessed using International Conference of Harmonization (ICH) parameters, where linearity, accuracy, selectivity, and robustness of the method were investigated. Correlations were above 0.99, accuracy results ranged from 97.6 to 102.8 % and limits for detection and quantitation (LOD and LOQ) values were determined for each vitamin in μg/mL except for FA and BT in ng/mL. LOD values were between 0.006 and 15.08 μg/mL while LOQ values ranged from 0.031 to 49.77 μg/mL. Stability studies were conducted under stressed conditions and degradation percentages were computed. Where, VB5, VB6, FA and PB, VC, and NC were the most degradable vitamins. Whiteness evaluation using the modern RGB 12 algorithm compared our method and the old reported one by Sasaki et al., 2020. The comparison favored our newly developed method in terms of analytical performance, practical applicability and greenness. Besides, AGREE and GAPI soft wares were used to assess the greenness of the method. It was clear that the results of colored pictograms confirm low hazardous impact and that the new method is greener with AGREE score of 0.66. Furthermore, the functionality and applicability of the novel HPLC approach were concluded via the Blue Applicability Grade Index (BAGI) tool with a final score of 82.5.

Distinguishing Turkish pine honey from multi-floral honey through MALDI-MS-based N-glycomics and machine learning

Honey, a multifaceted blend of sugars, amino acids, vitamins, proteins, and minerals, exhibits compositional variability dependent upon the floral source. While previous studies have attempted to categorize honey, the use of glycomic profiles for honey classification remains an unexplored avenue. This investigation seeks to establish a methodology for distinguishing honey types, specifically multi-floral and pine honey, employing mass spectrometry-based glycomic analysis in tandem with machine learning. In this search, seven samples of pine honey and eight samples of multi-floral honey were obtained from diverse regions of Turkey. Subsequently, the proteins within these honey samples were extracted, and glycans were enzymatically released. The released glycans were labeled with 2-aminobenzoic acid (2-AA) and subjected to analysis via matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS). The glycan profiles of pine and multi-floral honey were determined through these analytical procedures, revealing a total of 76 distinct N-glycan structures. Among these, 13 N-glycan profiles consistently established at high levels across experimental replicates and were incorporated in subsequent analyses. Following the quantification of individual glycan abundances, statistically significant differences in glycan profiles were determined. Notably, N-glycans Hex5HexNAc2, Hex4HexNAc3, and Hex5HexNAc3 displayed considerable differences. Using the 13 N-glycan profiles, an accuracy rate of 93.5% was obtained from machine learning analysis, which increased to 100% when incorporating the identified significantly changed glycans. The most productive models were identified as “subspace and fine k-nearest neighbors (KNN).” The findings underscore the potential of mass spectrometry-based glycomics in conjunction with machine learning as a robust tool for precise honey type classification and its prospective utility in quality control and honey product authentication.

Rapid method for quantitation of seven human milk oligosaccharides in infant formula and premix

As the evidence supporting the beneficial effects of human milk oligosaccharides (HMOs) grows, so does the commercial interest in their inclusion in infant formula products. This also requires analytical methods capable of their quantification from finished infant formula products as well as from premixed ingredients in some cases. The objective of the present study was the development and single-laboratory validation of a method that can be used for this purpose for seven HMOs: 2′-fucosyllactose (2′FL), 3-fucosyllactose (3FL), difucosyllactose (DFL), 3′-sialyllactose (3′SL), 6′-sialyllactose (6′SL), lacto-N-tetraose (LNT), and lacto-N-neotetraose (LNnT).The present method uses labeling by reductive amination, with 4-aminobenzoic acid ethyl ester (benzocaine) as the labeling reagent and picoline borane as the reducing agent, then applies HPLC separation with UV detection.The seven HMOs could be analyzed from infant formula and premix samples with recoveries between 91 and 108 %, relative standard deviations of 4.3 % or lower across all replicates, and limits of quantitation between 0.001 % and 0.004 % of powder sample by weight.The method was found to be rapid and reliable, with a runtime of only 14 min per injection, in contrast to other methods found in literature which typically use nearly or more than an hour. In addition, it uses instrumentation that's readily available in most analytical laboratories.

Facile synthesis of anthranilic acid based dual functionalized novel hyper cross-linked polymer for promising CO2 capture and efficient Cr3+ adsorption

A novel hyper cross-linked polymer of 2-Aminobenzoic acid (HCP-AA) is synthesized for the adsorption of Cr3+ and CO2. The Brunauer–Emmett–Teller surface area of HCP-AA is 615 m2 g−1. HCP-AA of particle size 0.5 nm showed maximum adsorption of Cr3+ for lab prepared wastewater (93%) while it was 88% for real industrial wastewater. It is might be due to electrostatic interactions, cation-π interactions, lone pair interactions and cation exchange at pH 7; contact time of 8 min; adsorbent dose 0.8 g. The adsorption capacity was calculated 52.63 mg g−1 for chromium metal ions at optimum conditions. Freundlich isotherm studies R2 = 0.9273 value is the best fit and follows pseudo second order kinetic model (R2 = 0.979). The adsorption is found non-spontaneous and exothermic through thermodynamic calculations like Gibbs free energy (ΔG), enthalpy change (ΔH) and entropy change (ΔS) were 6.58 kJ mol−1, − 60.91 kJ mol−1 and − 45.79 kJ mol−1 K−1, respectively. The CO2 adsorption capacity of HCP-AA is 1.39 mmol/g with quantity of 31.1 cm3/g (6.1 wt%) at 273Kwhile at 298 K adsorption capacity is 1.12 mmol/g with quantity 25.2 cm3/g (5 wt%). Overall, study suggests that carboxyl (–COOH) and amino (–NH2) groups may be actively enhancing the adsorption capacity of HCP-AA for Cr3+ and CO2.

Engineering polyamide materials: s-triazine framework with specialized bulky side chains for advanced applications

The focus of this study is on the synthesis of organic fluorescent and thermally stable polyamides using an s-triazine frame. Coumarin and n-phenyl anthranilic acid have been utilized as bulky pendent groups in the synthesis of the monomer, resulting in polyamides with two groups that enhance stability and fluorescence. The synthesized polyamides have been characterized using a variety of techniques. The thermal stability of the polyamides has been studied using thermogravimetric analysis. These polyamides offer appealing features such as fluorescence and enhanced thermal stability, making them significant for a wide range of applications, including biosensors, clean energy technologies, and explosive sensing.

Aminobenzoic acid and prospects of its use in ophthalmology practice

Aminobenzoic acid is a biologically active substance widespread in nature, which has a wide range of therapeutic applications as an antiviral, antibacterial, antioxidant, antimutagenic, anticoagulant, fibrinolytic, immunomodulatory, radioprotective agent. As an interferon inducer it has been used for many years in mono- and complex therapy of viral eye lesions: conjunctivitis, keratoconjunctivitis, keratouveitis, including those caused by the herpes virus (Herpes simplex, Herpes zoster), adenoviruses; keratopathies of infectious, post-traumatic and postoperative origin. Taking into account the available information, a new drug has been registered and introduced into clinical practice, the main active ingredient of which is 0.007% aminobenzoic acid – Exinta. However, a number of studies have also shown the effectiveness of аminobenzoic acid in the treatment of neurodegenerative eye diseases by reducing the intensity of oxidative damage by lipid peroxidation products, as well as increasing the activity of transport adenosine triphosphatases in eye tissues. Based on the results obtained, it is recommended to use a 0.007% aminobenzoic acid solution not only for the treatment of viral eye diseases as an interferon inducer, but also in the treatment of uveitis, burns and eye injuries, retinal dystrophies, retinopathy, after ophthalmological operations, inflammatory and dystrophic diseases of the cornea, for keratopathies of various origins, for accommodation disorders, etc. In the given clinical example, 0.007% aminobenzoic acid showed its effectiveness in the lingering course of chronic conjunctivitis in the background of the low effectiveness of other drugs, where with the help of monotherapy it was possible to achieve clinical recovery.

Plant-based zinc nanoflowers assisted molecularly imprinted polymer for the design of an electrochemical sensor for selective determination of abrocitinib

The first electrochemical sensor application in the literature is described for the sensitive and selective determination of the selective Janus kinase (JAK)-1 inhibitor abrocitinib (ABR). ABR is approved by the U.S. Food and Drug Administration (FDA) for the treatment of atopic dermatitis. The molecularly imprinted polymer (MIP)-based sensor was designed to incorporate zinc nanoflower (ZnNFs)-graphene oxide (GO) conjugate (ZnNFs@GO), synthesized from the root methanolic extract (RME) of the species Alkanna cappadocica Boiss. et Bal. to improve the porosity and effective surface area of the glassy carbon electrode (GCE). Furthermore, the MIP structure was prepared using ABR as a template molecule, 4-aminobenzoic acid (4-ABA) as a functional monomer, and other additional components. Scanning electron microscopy (SEM), X-ray diffraction (XRD), and Fourier transform infrared spectroscopy (FTIR) were used to characterize the surface and structure of the synthesized nanomaterial and MIP-based surface. Among the electrochemical methods, cyclic voltammetry (CV) and electrochemical impedance spectroscopy (EIS) were preferred for detailed electrochemical characterization, and differential pulse voltammetry (DPV) was preferred for all other electrochemical measurements using 5.0 mM [Fe(CN)6]3–/4– solution as the redox probe. The MIP-based sensor, which was the result of a detailed optimization phase, gave a linear response in the 1.0 × 10–13 – 1.0 × 10–12 M range in standard solution and serum sample. The obtained limit of detection (LOD) and limit of quantification (LOQ) values and recovery studies demonstrated the sensitivity, accuracy, and applicability of the sensor. Selectivity, the most important feature of the MIP-based sensor, was verified by imprinting factor calculations using ibrutinib, ruxolitinib, tofacitinib, zonisamide, and acetazolamide.Graphical

New Cocrystals of Ligustrazine: Enhancing Hygroscopicity and Stability.

Ligustrazine (TMP) is the main active ingredient extracted from Rhizoma Chuanxiong, which is used in the treatment of cardiovascular and cerebrovascular diseases, with the drawback of being unstable and readily sublimated. Cocrystal technology is an effective method to improve the stability of TMP. Three benzoic acid compounds including P-aminobenzoic acid (PABA), 3-Aminobenzoic acid (MABA), and 3,5-Dinitrobenzoic acid (DNBA) were chosen for co-crystallization with TMP. Three novel cocrystals were obtained, including TMP-PABA (1:2), TMP-MABA (1.5:1), and TMP-DNBA (0.5:1). Hygroscopicity was characterized by the dynamic vapor sorption (DVS) method. Three cocrystals significantly improved the hygroscopicity stability, and the mass change in TMP decreased from 25% to 1.64% (TMP-PABA), 0.12% (TMP-MABA), and 0.03% (TMP-DNBA) at 90% relative humidity. The melting points of the three cocrystals were all higher than TMP, among which the TMP-DNBA cocrystal had the highest melting point and showed the best stability in reducing hygroscopicity. Crystal structure analysis shows that the mesh-like structure formed by the O-H⋯N hydrogen bond in the TMP-DNBA cocrystal was the reason for improving the stability of TMP.

Photocatalytic degradation of p-aminobenzoic acid on N-biomass charcoal etched with Fe-Al-bilayer hydroxide: New insights through spectroscopic investigation

We investigated the photocatalytic property of etched iron‑aluminum layered double hydroxide (LDH) composites using urea-modified biochar (N-BC) carrier to degrade para-aminobenzoic acid (PABA), a refractory organic pollutant. The prepared FeAl-LDH@FeSx-N-BC composite exhibited excellent photocatalytic performance, attributed to the enhanced photogenerated charge-carrier separation by the etched LDH and the improved comparative surface areas by the doped N-BC. The composite photocatalytically degraded 96 % of PABA. The performance was affected by solute concentration, pH and photocatalyst dose. Adding p-benzoquinone and EDTA-2Na significantly decreased the degradation rate, suggesting that superoxide radicals and holes were co-involved in PABA degradation. The excellent PABA removal efficiency was consistent for three consecutive runs. The samples' reactive oxygen species was confirmed, as electron paramagnetic reverberation explained the photodegradation mechanism. Under xenon lamp irradiation, two PABA photocatalytic degradation pathways were proposed using Liquid Chromatograph Mass Spectrometer (LCMS) and density functional theory. As expected, FeAl-LDH@FeSx-N-BC showed excellent photocatalytic performance, expanding a new direction and possibility for future photocatalytic treatment of water pollutants.

Phase separation, aggregation, and complexation of triton-X100 and bovine serum albumin mixture: A combined cloud point and UV–visible spectroscopic approaches

Phase separation and aggregation behaviour of triton X-100 (TX-100) and bovine serum albumin (BSA) mixture were investigated using cloud point and UV–visible spectroscopic techniques. The effects of various hydrotropes (HYTs) - namely, sodium salicylate (SS), sodium benzoate (SB), glycerol (Glyc), and 4-aminobenzoic acid (4-ABA) - on the cloud point (CP) of TX-100 + BSA were determined. The obtained CP values for the mixed system in the presence of HYTs followed the order:CPH2O+4−ABA<CPH2O+Glyc<CPH2O+SB<CPH2O+SS. The measured critical micellization concentration (CMC) values of the TX-100 + BSA mixture were found to be significantly altered with varying amounts of BSA. The calculated free energy of clouding and micellization indicated the non-spontaneous nature of the phase transition and the spontaneous association of the TX-100 + BSA mixture. The non-spontaneity of phase separation decreased with increasing concentrations of HYTs. The enumerated values of ∆Hco and ∆Sco were consistently recorded as negative and positive magnitudes, respectively, in all aqueous HYTs media. The clouding process occurred due to a combination of hydrophobic and electrostatic interactions. The binding constant of the mixed system was determined employing the UV–vis spectroscopic method using the Benesi-Hildebrand equation.

A Novel RP-UHPLC-MS/MS Approach for the Determination of Tryptophan Metabolites Derivatized with 2-Bromo-4'-Nitroacetophenone.

Many biologically active metabolites of the essential amino acid L-tryptophan (Trp) are associated with different neurodegenerative diseases and neurological disorders. Precise and reliable methods for their determination are needed. Variability in their physicochemical properties makes the analytical process challenging. In this case, chemical modification of analyte derivatization could come into play. Here, we introduce a novel fast reversed-phase ultra-high-performance liquid chromatography (RP-UHPLC) coupled with tandem mass spectrometry (MS/MS) method for the determination of Trp and its ten metabolites in human plasma samples after derivatization with 2-bromo-4'-nitroacetophenone (BNAP). The derivatization procedure was optimized in terms of incubation time, temperature, concentration, and volume of the derivatization reagent. Method development comprises a choice of a suitable stationary phase, mobile phase composition, and gradient elution optimization. The developed method was validated according to the ICH guidelines. Results of all validation parameters were within the acceptance criteria of the guideline, i.e., intra- and inter-day precision (expressed as relative standard deviation; RSD) were in the range of 0.5-8.2% and 2.3-7.4%, accuracy was in the range of 93.3-109.7% and 94.7-110.1%, limits of detection (LODs) were in the range of 0.15-9.43 ng/mL, coefficients of determination (R2) were higher than 0.9906, and carryovers were, in all cases, less than 8.8%. The practicability of the method was evaluated using the blue applicability grade index (BAGI) with a score of 65. Finally, the developed method was used for the analysis of Alzheimer's disease and healthy control plasma to prove its applicability. Statistical analysis revealed significant changes in picolinic acid (PA), anthranilic acid (AA), 5 hydroxyindole-3-acetic acid (5-OH IAA), and quinolinic acid (QA) concentration levels. This could serve as the basis for future studies that will be conducted with a large cohort of patients.

Probing the Molecular and Macroscopic Structure of Solid Solutions by Dynamic Nuclear Polarization (DNP) Enhanced 13C and 15N Solid-State NMR Spectroscopy.

Crystallization is a widely used purification technique in the manufacture of active pharmaceutical ingredients (APIs) and precursor molecules. However, when impurities and desired compounds have similar molecular structures, separation by crystallization may become challenging. In such cases, some impurities may form crystalline solid solutions with the desired product during recrystallization. Understanding the molecular structure of these recrystallized solid solutions is crucial to devise methods for effective purification. Unfortunately, there are limited analytical techniques that provide insights into the molecular structure or spatial distribution of impurities that are incorporated within recrystallized products. In this study, we investigated model solid solutions formed by recrystallizing salicylic acid (SA) in the presence of anthranilic acid (AA). These two molecules are known to form crystalline solid solutions due to their similar molecular structures. To overcome challenges associated with the long 1H longitudinal relaxation times (T1(1H)) of SA and AA, we employed dynamic nuclear polarization (DNP) and 15N isotope enrichment to enable solid-state NMR experiments. Results of solid-state NMR experiments and DFT calculations revealed that SA and AA are homogeneously alloyed as a solid solution. Heteronuclear correlation (HETCOR) experiments and plane-wave DFT structural models provide further evidence of the molecular-level interactions between SA and AA. This research provides valuable insights into the molecular structure of recrystallized solid solutions, contributing to the development of effective purification strategies and an understanding of the physicochemical properties of solid solutions.

EXPANDED PERLITE MELANOID PIGMENT FORMATION WITH PARTICIPATION OF AMINOBENZOIC ACID

In a determinate sense, Maillard reaction is identified with generation of brown-colored compounds or melanoidins in the reaction environment. Despite this fact, the stage of colored compound formation is episodically studied only [7]. It is established that coloring is related to formation of highly-molecular compounds (&gt; 12000 Dalton) or melanoidins. As a rule, this mass contains heterogenic mixture of melanoidins, and each of them has the different absorption maximum. The intensity of color of our compound is predetermined by high concentration of these compounds, which have intense absorption in the ultraviolet region. Using the similar techniques, we have studied the distribution of melanoid pigment (λ = 470 nm) among low-molecular (&lt;3500 Dalton) and highly-molecular fractions, in reaction mixture obtained via interaction of m-aminobenzoic acid and D-glucose. Results are given in the first figure. Components, which didnt enter into reaction have been determined during reaction, in samples taken from reaction mixture in the definite intervals of time. Reaction mixture has been divided on paper or in thin layer. index terms- Maillard reaction, m-aminobenzoic acid, p-aminobenzoic acid, pH - metre, melanoid pigment.

Synthesis and Characterization of some new heterocyclic derivatives from aromatic carbonyl ‎compounds and carboxylic acids with Evaluation some of them for biological activity

In this research investigation, a total of eighteen diverse tetra- and penta-lateral cyclic compounds were synthesized. These included 1,3,4-thiadiazole, thiazolidin-4-one (via an alternative method), 1,2,4-triazole, carbothioamide, thiazole-4-one, azetidin-2-one, and oxazole. The synthesis procedure entailed a sequence of reactions. The thiazolidine-4-one 1 was obtained by reaction p-aminobenzoic acid with thiosemicarbazide, followed by treatment with p-tolualdehyde to produce Schiff base 2. Reaction Schiff base 2 with mercaptoacetic acid in dry benzene was carried out to produce thiazolidine-4-one 3. In another synthesis pathway, the esterification of p-nitro benzoic acid with ethanol in the presence of sulfuric acid was obtained to formation of compound 4. Compound 4 was subsequently reacted with thiosemicarbazide, yielding compound 5. Cyclization of compound 5 was then achieved using 4% sodium hydroxide solution. This formed the 1,2,4-triazole heterocycle, designated compound 6. Thiosemicarbazone 7-9 were prepared by reaction of thiosemicarbazide with different aldehydes. Additionally, 2-substituted-1,3-thiazolidine-4-one derivatives 10-12 were synthesized through the reaction of thiosemicarbazone with chloroacetic acid in the presence of anhydrous sodium acetate. The Oxazole derivative 15 was obtained through a series of reactions starting with the reaction of p-amino benzoic acid with ethyl chloroacetate, resulting in compound 13. Compound 13 was then treated with urea to obtain compound 14, followed by a reaction with 4-phenyl phenacyl bromide to yield the final product, the Oxazole derivative 15. The 2-aminooxadiazole derivative 16 was synthesized by reaction urea with 4-bromoacetophenone which was reacted with 4-bromobenzaldehyde to produce Schiff base derivative 17. Finally, β-lactam 18 is obtained through reaction Schiff base with chloroacetyl chloride in the presence of triethyl amine. FT-IR, 1H-NMR, and 13C-NMR spectroscopy were used to confirm their proposed structures. Moreover, the antibacterial and antifungal activities of certain synthesized compounds, specifically 2,3,6,11,13,15,17, and 18, were assessed against Staphylococcus aureus, Escherichia coli, and Candida albicans, demonstrating encouraging outcomes.Keywords: Antibacterial, antifungal activity, oxadaizole, heterocyclic derivatives, Oxazole.

Novel Azidobenzohydrazide Schiff Bases: Unveiling Effective Synthesis Strategy and Antimicrobial Efficacy Evaluation

AbstractBenzohydrazide analogues are interesting compounds in the field of pharmaceutical, medicinal chemistry, and coordination chemistry, since they are diverse in biological activities, and they are contributing in medicines and drugs. In the present paper, a series of 4‐azido‐N’‐(benzylidene)benzohydrazides have been synthesized with excellent yields via a four steps procedure from amino benzoic acid as the starting substrate. The products have been fully characterized and their antimicrobial activity evaluated by disc diffusion procedure. Notably, such compounds exhibits activity against gram‐positive and gram‐negative bacteria and fungi.