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We have developed a green and efficient protocol for the chalcogenation of bicyclic arenes by using I2/DMSO as catalytic system under solvent- and metal-free conditions. This protocol allows access to several chalcogenated bicyclic arenes through C(sp²)-H bond functionalization, in good to excellent yields by using microwave irradiation or conventional heating. [ABSTRACT FROM AUTHOR]

Wastewater is used as an alternate source of irrigation in densely populated areas all over the world. Unfortunately untreated wastewater when used to irrigate the crops becomes a source of trace elements contamination to soils and crops and can cause severe health effect on animals and humans. The present study was designed to evaluate the long term application of wastewater on trace elements (Cd, Co, Cr, Cu, and Zn) accumulation in soil and edible and non-edible parts of sugarcane. Samples of soil, sugarcane root, shoot and leaf irrigated with uncontaminated water (clean water) and untreated wastewater (industrial+municipal) were collected in triplicate and analyzed for total Cd, Cr, Co, Cu, and Zn content with ICP-MS and Atomic Absorption Spectrophotometer (AAS). The results of this study show that electrical conductivity (EC) and total dissolved solids (TDS) of uncontaminated water were 490µS/cm and 245ppm and wastewater ranged from 790 to 3550 µS/cm and 396-1775ppm. The salinity of wastewater ranged from 0.2 to 0.8. Cadmium and Co was present at very low concentration in uncontaminated and wastewater. Chromium, Cu and Zn in wastewater ranged from 1.07-4.62, 0.19-10 and 0.078-0.197 mL per L. Chromium and Cu exceed the safe limit in wastewater. The concentration of such elements in wastewater remained in the safe limit for crops. Soils irrigated with wastewater was likely to exceed the safe limits of Cr and Cu once irrigated with wastewater. Sugarcane root shows no accumulation of any of the trace elements. Bio-concentration factor or plant concentration factor (BCF or PCF) of Cd, Cr, Cu and Zn was less than 1 in all soils irrigated with wastewater. Whereas BCF and PCF of Co was more than 1 in soil irrigated with uncontaminated water (soil A) and soil irrigated with wastewater (soil B). [ABSTRACT FROM AUTHOR]

Herein, we report a new and solvent-free methodology for the preparation of vinyl thioethers from terminal alkynes and thiols, using magnetite (Fe3O4) nanoparticles as a recyclable catalyst. With this greener method, the desired vinyl thioethers were achieved in good yields and with good stereoselectivity. In addition, the catalyst was easily recovered using a simple external magnet and reused for further catalytic reactions without significant loss of activity up to the fifth cycle. [ABSTRACT FROM AUTHOR]

Highly efficient molecular-iodine-catalyzed chalcogenations (S and Se) of imidazo[1,2- a]pyridines were achieved by using diorganoyl dichalcogenides under solvent-free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 % yield by using DMSO as an oxidant, in the absence of a metal catalyst, and under an inert atmosphere. This mild, green approach allowed the preparation of different types of chalcogenated imidazo[1,2- a]pyridines with structural diversity. Furthermore, the current protocol was also extended to other N-heterocyclic cores. [ABSTRACT FROM AUTHOR]

This article describes the synthesis and liquid crystal properties of new compounds that are derived from gallic acid. All the compounds were characterised by1H and13C nuclear magnetic resonance spectroscopy (1H NMR and13C NMR), Infrared spectroscopy (IR) and Elemental analysis (CHN). The mesophases of these compounds were characterised using polarising optical microscopy (POM), differential scanning calorimetry (DSC) and SAXS measurements. The morphology of the surface of the films was investigated using atomic force microscopy (AFM). Compounds9and13, which remain in a supercooled state until room temperature, do not exhibit liquid crystalline behaviour. The other compounds (i.e.,5, 7and8) self-assemble into tubular supramolecular architectures generating hexagonal columnar (Colh) mesophases, which was confirmed by SAXS measurements. [ABSTRACT FROM AUTHOR]

In the present study, two species Hypericum x moserianum and Hypericum ericoides which belong to genus Hypericum were evaluated for their potential antiglycation, antioxidant, anti lipid peroxidation and cytotoxic activities. These species are widely used in folk medicine and to the best of our knowledge there were no previous reports regarding antioxidant, anti-glycation and cytotoxicity studies of these species. Among the crude methanol extracts and fractions of both the species, the ethyl acetate fraction of H. x moserianum exhibited promising antioxidant activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 129.084±1,215µg/ml, followed by methanol extract (IC50=232.083±1.215µg/ml) and aqueous fraction (IC50=266.962±2.213µg/ml). The ethyl acetate fraction of H. ericoides exhibited IC50 value of 295.088±2.320µg/in 1. In antiglycation assay, the ethyl acetate fraction of H. x moserianum showed 52.096% inhibition at 500µg/ml. For lipid peroxidation assay, the dichloromethane, aqueous and n- hexane fractions of H. x moserianum showed 67.241, 66.147 and 64.213% inhibition respectively, while aqueous fraction of H. ericoides exhibited 67.404% inhibition at 500µg/ml. In cytotoxicity assay, all fractions of both the species were found to be non-toxic on mouse fibroblast 3T3 cells with IC50 value greater than 30µg/ml as compared to cycloheximide with IC50 value 0.073±0.1 µg/ml used as a standard. It was concluded from the study that among the two species, crude methanolic and ethyl acetate fractions were more active regarding the antioxidant, anti-glycation activities while dichloromethane, aqueous and n-hexane fractions possessed anti-lipid peroxidation activity. [ABSTRACT FROM AUTHOR]

An efficient, economical, and green K2CO3-promoted procedure for the synthesis of selenated and thiolated oxadiazoles through C-H bond functionalization in the absence of metal catalyst is developed. [ABSTRACT FROM AUTHOR]

• A convenient synthesis of the title compounds. • The most active compounds exhibit strong binding affinity in docking. • AchE inhibition much better than standard. • Ethyl 2-(2-(4-methoxybenzylidene)(benzyl)hydrazinyl)thiazole-4-carboxylate may further tested to be used against Alzheimer disease. A series of N -alkylated and N -benzylated thiazole-4-carboxylates (3a-n) were prepared via alkylation/benzylation of ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates (1). The structures of all synthesized thiazoles were established with FT-IR, 1H-, 13C-NMR and HRMS spectroscopic techniques. All synthesized compounds were screened as inhibitors of acetylcholinesterase (AChE), using galanthamine as the standard. The AChE activity results revealed, that the compounds ethyl 2-(2-(4-methoxybenzylidene)(benzyl)hydrazinyl)thiazole-4-carboxylate (3n) and ethyl 2-(2-(4-methylbenzylidene)(decyl)hydrazinyl)thiazole-4-carboxylate (3k) were moderate inhibitor with IC 50 values 9.56 ± 2.76 and 9.92 ± 0.96 µM, (better than the standard). Simulation studies based on virtual screening of AChE inhibition by molecular docking predicted the binding free energies and molecular inhibition of 3f, 3k and 3n compounds (∆G= - 7.73, ∆G= - 7.91 and ∆G= - 8.13) was comparable with galanthamine. These three compounds occupied the same binding cavity as galanthamine, with greater affinity. Furthermore, in silico, all other compounds also exhibited moderate to good AChE inhibition activities. [Display omitted] [ABSTRACT FROM AUTHOR]

In pursuit of potential agents to treat Chagas disease and leishmaniasis, we report the design, synthesis, and identification novel naphthoquinone hydrazide-based molecular hybrids. The compounds were subjected to in vitro trypanocide and leishmanicidal activities. N'-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)-3,5-dimethoxybenzohydrazide (13) showed the best performance against Trypanosoma cruzi (IC50 1.83 µM) and Leishmania amazonensis (IC50 9.65 µM). 4-Bromo-N'-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzohydrazide (16) exhibited leishmanicidal activity (IC50 12.16 µM). Regarding trypanocide activity, compound 13 was low cytotoxic to LLC-MK2 cells (SI = 95.28). Furthermore, through molecular modeling studies, the cysteine proteases cruzain, rhodesain and CPB2.8 were identified as the potential biological targets.

Phenoselenazines are nitrogen and selenium-based heterocyclic compounds that have important biological activities. However, their preparation methods are scarce and difficult to handle. The synthesis of a phenoselenazine from a simple and robust CuO nanoparticle catalyzed methodology, using bis-aniline-diselenide and 1,2-dihalobenzenes under microwave irradiation. Also, the double-cross-coupling reaction mechanism for C-Se and C-N bond formation, including the observation of a reaction intermediate by mass spectrometry have been studied.

Herein, we report a KIO 3 -catalyzed oxidative coupling of thiols to their corresponding disulfides in water, in a short time and at ambient temperature. The reaction has a broad scope and exhibits good functional group tolerance, resulting in the desired products in excellent yields. This approach allows the reuse of the reaction system in multiple cycles and scale-up. Furthermore, the current protocol demonstrates compatibility for in situ generation of disulfides and post application in C(sp 2 )-H bond sulfenylation.

Leishmaniasis remains a significant global health concern, with current treatments relying on outdated drugs associated with high toxicity, lengthy administration, elevated costs, and drug resistance. Consequently, the urgent need for safer and more effective therapeutic options in leishmaniasis treatment persists. Previous research has highlighted selenium compounds as promising candidates for innovative leishmaniasis therapy. In light of this, a library of 10 selenium-containing diverse compounds was designed and evaluated in this study. These compounds included selenium-substituted indole, coumarin, chromone, oxadiazole, imidazo[1,2- a ]pyridine, Imidazo[2,1- b ]thiazole, and oxazole, among others. These compounds were screened against Leishmania amazonensis promastigotes and intracellular amastigotes, and their cytotoxicity was assessed in peritoneal macrophages, NIH/3T3, and J774A.1 cells. Among the tested compounds, MRK-106 and MRK-108 displayed the highest potency against L. amazonensis promastigotes with reduced cytotoxicity. Notably, MRK-106 and MRK-108 exhibited IC 50 values of 3.97 µM and 4.23 µM, respectively, and most of the tested compounds showed low cytotoxicity in host cells (CC 50 > 200 µM). Also, compounds MRK-107 and MRK-113 showed activity against intracellular amastigotes (IC50 18.31 and 15.93 µM and SI 12.55 and 10.92, respectively). In conclusion, the identified selenium-containing compounds hold potential structures as antileishmanial drug candidates to be further explored in subsequent studies. These findings represent a significant step toward the development of safer and more effective therapies for leishmaniasis, addressing the pressing need for novel and improved treatments.

Schiff bases represent a valuable class of organic compounds, synthesized via condensation of primary amines with ketones or aldehydes. They are renowned for possessing innumerable applications in agricultural chemistry, organic synthesis, chemical and biological sensing, coating, polymer and resin industries, catalysis, coordination chemistry, and drug designing. Schiff bases contain imine or azomethine (-C=N-) functional groups which are important pharmacophores for the design and synthesis of lead bioactive compounds. In medicinal chemistry, Schiff bases have attracted immense attention due to their diverse biological activities. This review aims to encompass the recent developments on the antimicrobial activities of Schiff bases. The article summarizes the antibacterial, antifungal, antiviral, antimalarial, and antileishmanial activities of Schiff bases reported since 2011., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

Leishmaniases are among the neglected tropical diseases that still cause devastating health, social, and economic consequences to more than 350 million people worldwide. Despite efforts to combat these vector-borne diseases, their incidence does not decrease. Meanwhile, current antileishmanial drugs are old and highly toxic, and safer presentations are unaffordable to the most severely affected human populations. In a previous study by our research group, we synthesized 17 flavonoid derivatives that demonstrated impressive inhibition capacity against rCPB2.8, rCPB3, and rH84Y. These cysteine proteases are highly expressed in the amastigote stage, the target form of the parasite. However, although these compounds have been already described in the literature, until now, the amastigote effect of any of these molecules has not been proven. In this work, we aimed to deeply analyze the antileishmanial action of this set of synthetic flavonoid derivatives by correlating their ability to inhibit cysteine proteases with the action against the parasite. Among all the synthesized flavonoid derivatives, 11 of them showed high activity against amastigotes of Leishmania amazonensis , also providing safety to mammalian host cells. Furthermore, the high production of nitric oxide by infected cells treated with the most active cysteine protease B (CPB) inhibitors confirms a potential immunomodulatory response of macrophages. Besides, considering flavonoids as multitarget drugs, we also investigated other potential antileishmanial mechanisms. The most active compounds were selected to investigate another potential biological pathway behind their antileishmanial action using flow cytometry analysis. The results confirmed an oxidative stress after 48 h of treatment. These data represent an important step toward the validation of CPB as an antileishmanial target, as well as aiding in new drug discovery studies based on this protease.

Herein, we describe a urea hydrogen peroxide-mediated sustainable protocol for the synthesis of selenylated imidazo[2,1- b ]thiazole by using half molar equivalent diorganyl diselenides in ethyl lactate as a greener solvent. The reaction features high yields, easy performance on gram scale, metal-free conditions, as well as applicability to imidazopyridine and imidazopyrimidine., Competing Interests: The authors declare no competing financial interest., (© 2023 The Authors. Published by American Chemical Society.)

In this paper, we report an eco-friendly approach for the C(sp 2 )-H bond selenylation of imidazopyridines and other N-heteroarenes as well as simple arenes at ambient temperature. This new protocol consists of the reaction between (N-hetero)-arenes and the diorganyl-diselenides and trichloroisocyanuric acid (TCCA)-ethanol reagent system. In a short reaction time, the desired selenylated products were obtained regioselectively in good yields, with tolerance for a wide range of functional groups., (© 2023. Springer Nature Limited.)

This study describes the synthesis of new pyromellitic diimide (PMDI) derivatives obtained in good yields from the reaction between pyromellitic dianhydride and aminobenzazoles reactive to proton-transfer in the excited state (ESIPT). In this investigation, a non-ESIPT PMDI was also prepared for comparison. These compounds presented absorption maxima in the ultraviolet region attributed to the allowed 1 π-π* electronic transitions. Redshifted absorptions were observed for the ESIPT compounds (3b-3c) due to their π-extended conjugation if compared to the non-ESIPT dye (3a). The compounds presented fluorescence emissions between 300 and 600 nm, dependent on the solvent polarity and their chemical structures. While compound 3a presents a single emission, a dual fluorescence could be observed for compounds 3b-3c. As expected for ESIPT compounds, the emission at higher energies could be related to the excited enol conformer (E*), and the emission with a large Stokes shift was attributed to the keto tautomer (K*). All compounds presented fluorescence emission in the solid state, whereas the ESIPT derivatives presented redshifted emissions with a large Stokes shift, as expected. Cyclic voltammetry was employed to investigate the electrochemical properties of these compounds. The HOMO and LUMO energy levels were estimated at -5.40 to -5.00 eV and -2.84 to -2.62 eV, and good thermal stability (T d  > 150 °C) was observed. Quantum chemical calculationsusingTD-DFT and DFT were performed to investigate the electronic and photophysical features of the molecules., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier B.V. All rights reserved.)

We report an electrochemical oxidative intramolecular cyclization reaction between 2-alkynylphenol derivatives and different diselenides species to generate a wide variety of substituted-benzo[ b ]furans. Driven by the galvanostatic electrolysis assembled in an undivided cell, it provided efficient transformation into oxidant-, base-, and metal-free conditions in an open system at room temperature. With satisfactory functional group compatibility, the products were obtained in good to excellent yields., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2022 Doerner, Scheide, Nicoleti, Durigon, Idiarte, Sousa, Mendes, Saba, Neto, Martins, Rafique and Braga.)

Glioblastoma multiforme (GBM) is a notably lethal brain tumor associated with high proliferation rate and therapeutic resistance, while currently effective treatment options are still lacking. Imidazo[1,2- a ]pyridine derivatives and organoselenium compounds are largely used in medicinal chemistry and drug development. This study is aimed at further investigating the antitumor mechanism of IP-Se-06 (3-((2-methoxyphenyl)selanyl)-7-methyl-2-phenylimidazol[1,2- a ]pyridine), a selenylated imidazo[1,2- a ]pyridine derivative in glioblastoma cells. IP-Se-06 exhibited high cytotoxicity against A172 cells (IC 50 = 1.8  μ M) and selectivity for this glioblastoma cell. The IP-Se-06 compound has pharmacological properties verified in its ADMET profile, especially related to blood-brain barrier (BBB) permeability. At low concentration (1  μ M), IP-Se-06 induced intracellular redox state modulation with depletion of TrxR and GSH levels as well as inhibition of NRF2 protein. IP-Se-06 also decreased mitochondrial membrane potential, induced cytochrome c release, and chromatin condensation. Furthermore, IP-Se-06 induced apoptosis by decreasing levels of Bcl-xL while increasing levels of γ -H2AX and p53 proteins. Treatment with IP-Se-06 induced cell cycle arrest and showed antiproliferative effect by inhibition of Akt/mTOR/HIF-1 α and ERK 1/2 signaling pathways. In addition, IP-Se-06 displayed significant inhibition of p38 MAPK and p-p38, leading to inhibition of inflammasome complex proteins (NLRP3 and caspase-1) in glioblastoma cells. These collective findings demonstrated that IP-Se-06 is a bioactive molecule that can be considered a candidate for the development of a novel drug for glioblastoma treatment., Competing Interests: The authors declare that there are no conflicts of interests., (Copyright © 2022 Daniela C. dos Santos et al.)

Herein, we report a KIO 4 -mediated, sustainable and chemoselective approach for the one-pot C(sp 2 )-H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields., (© 2021 Wiley-VCH GmbH.)

Imidazo[1,2-a]pyridines (IP) and organoselenium compounds have been widely exploited in medicinal chemistry due to their pharmacological activities. Hepatocellular carcinoma (HCC) has few treatment options, and unfortunately, the prognosis is poor. Thus, the development of novel therapeutic drugs is urgent. The present study aimed at evaluating the antitumor mechanism of selenylated IP against HepG2 cells and in vivo. The selenylated IP named IP-Se-06 (3-((2-methoxyphenyl)selanyl)-7-methyl-2-phenylimidazol[1,2-a]pyridine) showed high cytotoxicity against HepG2 cells (half-maximal inhibitory concentration [IC 50 ] = 0.03 µM) and selectivity for this tumor cell line. At nontoxic concentration, IP-Se-06 decreased the protein levels of Bcl-xL and increased the levels of p53, leading to inhibition of cell proliferation and apoptosis. This compound decreased the level of extracellular signal-regulated kinase 1/2 protein and changed the levels of proteins involved in the drive of the cell cycle, tumor growth, and survival (cyclin B1, cyclin-dependent kinase 2). In addition, IP-Se-06 decreased the number of cells in the S phase. In addition, IP-Se-06 led to increased generation of reactive oxygen species, changed antioxidant defenses, and caused DNA fragmentation. Finally, IP-Se-06 significantly inhibited the growth of Ehrlich ascites tumors in mice, increased survival time, and inhibited angiogenesis. Therefore, IP-Se-06 may be an important compound regarding the development of a therapeutic drug for HCC treatment., (© 2020 Wiley Periodicals LLC.)

Most pharmacological studies concerning the beneficial effects of organoselenium compounds have focused on their ability to mimic glutathione peroxidase (GPx). However, mechanisms other than GPx-like activity might be involved on their biological effects. This study was aimed to investigate and compare the protective effects of two well known [(PhSe) 2 and PhSeZnCl] and two newly developed (MRK Picolyl and MRK Ester) organoselenium compounds against oxidative challenge in cultured neuronal HT22 cells. The thiol peroxidase and oxidase activities were performed using the glutathione reductase (GR)-coupled assay. In order to evaluate protective effects of the organoselenium compounds against oxidative challenge in neuronal HT22 cells, experiments based on glutamate-induced oxytosis and SIN-1-mediated peroxynitrite generation were performed. The thiol peroxidase activities of the studied organoselenium compounds were smaller than bovine erythrocytes GPx enzyme. Besides, (PhSe) 2 and PhSeZnCl showed higher thiol peroxidase and lower thiol oxidase activities compared to the new compounds. MRK Picolyl and MRK Ester, which showed lower thiol peroxidase activity, showed higher thiol oxidase activity. Both pre- or co-treatment with (PhSe) 2 , PhSeZnCl, MRK Picolyl and MRK Ester protected HT22 cells against glutamate-induced cytotoxicity. (PhSe) 2 and MRK Picolyl significantly prevented peroxinitrite-induced dihydrorhodamine oxidation, but this effect was observed only when HT22 were pre-treated with these compounds. The treatment with (PhSe) 2 increased the protein expression of antioxidant defences (Prx3, CAT and GCLC) in HT22 cells. Taking together, our results suggest that the biological effects elicited by these compounds are not directly related to their GPx-mimetic and thiol oxidase activities, but might be linked to the up-regulation of endogenous antioxidant defences trough their thiol-modifier effects.

A series of selenylated-oxadiazoles were prepared and their interaction with DNA was investigated. The photophysical studies showed that all the selenylated compounds presented absorption between 270 and 329 nm, assigned to combined n→π* and π→π* transitions, and an intense blue emission (325-380 nm) with quantum yield in the range of Φ F  = 0.1-0.4. DFT and TD-DFT calculations were also performed to study the likely geometry and the excited state of these compounds. Electrochemical studies revealed the ionization potential energies (-5.13 to -6.01 eV) and electron affinity energies (-2.25 to -2.83 eV), depending directly on the electronic effect (electron-donating or electron-withdrawing) of the substituent attached to the product. Finally, the UV-Vis DNA interaction experiments indicated that the compounds can interact with the DNA molecule due to intercalation, except for 3g (which interacted via electrostatic interaction). Plasmid cleavage assay presented positive results only for 3f that presented the strongest interaction results. These results made the tested selenylated-oxadiazoles as suitable structures for the development of drugs and the design of structurally-related therapeutics., Competing Interests: The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (© 2020 Elsevier Ltd. All rights reserved.)

Herein, a greener approach to the eosin Y-Na 2 catalyzed, C(sp 2 )-H bond azo coupling of imidazoheteroarene with aryl diazonium salts is described, under acid free conditions. This direct photoredox process resulted in the corresponding azo products in good to excellent yields. Besides, this new approach could also be applicable to anilines, which is a poorly reactive substrate by other methods. The main features of this reaction are that it provides high yields and is gram-scalable and applicable to biologically relevant imidazoheteroarenes and -anilines., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Herein, we report a greener protocol for the synthesis of 3-Se/S-indoles and imidazo[1,2-a]pyridines through direct C(sp 2 )-H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO 3 as a non-toxic, easy-to-handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram-scale, metal- and solvent-free conditions as well as applicability to different types of N-heteroarenes., (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Highly efficient molecular-iodine-catalyzed chalcogenations (S and Se) of imidazo[1,2-a]pyridines were achieved by using diorganoyl dichalcogenides under solvent-free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 % yield by using DMSO as an oxidant, in the absence of a metal catalyst, and under an inert atmosphere. This mild, green approach allowed the preparation of different types of chalcogenated imidazo[1,2-a]pyridines with structural diversity. Furthermore, the current protocol was also extended to other N-heterocyclic cores., (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

In the mol-ecule of the title compound, C(12)H(15)N(3)O(2), the pyrazole ring is oriented at a dihedral angle of 49.64 (6)° with respect to the benzene ring. Intra-molecular O-H⋯O, N-H⋯O and C-H⋯O inter-actions result in the formation of a trifurcated hydrogen bond. In the crystal structure, inter-molecular N-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules, forming a network structure.