The tautomerism of 1-phenyl-1,2-dihydro-3H-pyrazol-3-One was investigated. An X-ray crystal structure analysis exhibits dimers of 1-phenyl-1H-pyrazol-3-ol units. Comparison of NMR (nuclear magnetic resonance) spectra in liquid state (1H, 13C, 15N) wi...
The acyl pyrazole derivative (3,5-di-tert-butylphenyl)(1H-pyrazol-1-yl)methanone was prepared simply and rapidly in 86% isolated yield by means of an oxidative functionalization reaction of an aldehyde with pyrazole. A substoichiometric quantity of 4...
The title compound, 1-phenyl-3,3-di(1H-pyrazol-1-yl)propan-1-one, was synthesized in a 52% yield for the first time by a one-step reaction between 1H-pyrazole and 1-phenylprop-2-yn-1-one (their ratio being 2:1) in solid Al2O3 at room temperature. The...
Carboxylation of bis(pyrazol-1-yl)alkanes by oxalyl chloride was studied. It was found that 4,4′-dicarboxylic derivatives of substrates with electron-donating methyl groups and short linkers (from one to three methylene groups) can be prepared...
The combination of two compounds with known antimicrobial activity may, in some cases, be an effective way to limit the resistance to antibiotics of specific pathogens. Molecules carrying pyrazole moiety are well known for their bioactive properties...
An efficient synthetic route to construct diverse pyrazole-based chalcones from 1-phenyl-1H-pyrazol-3-ols bearing a formyl or acetyl group on the C4 position of pyrazole ring, employing a base-catalysed Claisen–Schmidt condensation reaction, is...
The compound 2-(3,5-dimethyl-1H-pyrazol-1-yl)thiazolo[4,5-b]pyridine (1) was synthesized with a yield of 71% by the reaction of 1-(thiazolo[4,5-b]pyridine-2-yl)hydrazine and acetylacetone. The structure was characterized by a single-crystal X-ray str...
The title compound was prepared by treatment of 5-fluoro-1-phenylchromeno [2,3-c]pyrazol-4(1H)-one with aqueous dimethylamine. Detailed spectroscopic data (1H NMR, 13C NMR, 15N NMR, IR, MS) are presented.
New 4-oxo-4H-pyrazol-1,2-dioxides were tested for their antiplatelet effects. Compound 2i has the highest activity in the Born test with 200 nMol/L.
A series of novel bis(substituted pyrazol-4-ylcarbonyl)-substituted thioureas have been synthesized by the reactions of substituted pyrazol-4-ylcarbonyl isothiocyanates with different diamines under ultrasound irradiation and classical heating method...
Tris{4-[(1,3-diphenyl-1H-pyrazol-4-yl)methylene]-41-aminobiphenyl}amine was synthesized from N-(4-bromophenyl)-N-[(1,3-diphenyl-1H-pyrazol-4-yl)methylene]amine and tris(4-bromophenyl)amine based on Ullmann coupling reaction. The synthesized compound...
It is well known that both isoxazole ring as well as pyrazole ring possess various biological activities and they both show interesting antimicrobial activity [1,2,3].[...]
N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-4-methyl-N-tosylbenzenesulfonamide was efficiently synthesized in good yield through a triethylamine-mediated sulfonamidation reaction of 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine with 4-methylbenzenesulfo...
1,3,5-Tris{[N-(1,3-diphenyl-1H-pyrazol-4-yl)methylene]-4-aminophenyl}-benzene was synthesised from N-(4-bromophenyl)-N-[(1,3-diphenyl-1H-pyrazol-4-yl)-methylene]amine and 1,3,5-tribromobenzene by an Ullman coupling reaction. The synthesized compound...
The molecular structure of bis(pyrazol-1-yl)methane-4,4′-dicarboxylic acid (H2bpmdc) was determined by single crystal X-Ray diffraction analysis. The compound crystallizes in a monoclinic crystal system; the unit cell contains four formula unit...
Reactions of 1-(5-methyl)-1H-1,2,3-triazol-4-yl)ethan-1-ones and benzaldehydes in ethanol under basic conditions gave the corresponding chalcones. Reactions of the chalcones combined with thiosemicarbazide in dry ethanol containing sodium hydroxide a...
Pyridine (P1) and benzoic acid (P2) derivatives with pyrazole moieties were synthesized and evaluated as corrosion inhibitors for mild steel in acidic medium. The evaluation was performed by electrochemical impedance spectroscopy (EIS), potentiodynam...
A mixture of (3,5-dimethyl-1H-pyrazol-1-yl)methanol 1 [1] (1.84 g, 14.6 mmol) and 4-aminobenzoic acid 2 (1g, 7.3 mmol) in acetonitrile (50 mL) was stirred in a closed vessel at room temperature for 6 days [2,3,4].[...]
The title compound was obtained by the reaction of tosylated glycerol carbonate with 1-phenyl-1H-pyrazol-3-ol in a good 71% yield. Detailed spectroscopic data (1H-NMR, 13C-NMR, 15N-NMR, IR, MS) are presented.
A mixture of (3,5-dimethyl-1H-pyrazol-1-yl)methanol 1 [1] (1.86 g, 14.8 mmol) and 4-amino-acetophenone 2 (1g, 7.4 mmol) in acetonitrile (50 mL) was stirred in a closed vessel at room temperature for 6 days [2,3,4].[...]
The compound 2-((1,3-dimethyl-1H-pyrazol-5-yl)(methyl)carbamoyl)benzene-diazonium hydrogen sulfate (10) was reacted with copper sulfate and sodium chloride, in the presence of ascorbic acid as reducing agent, to afford a mixture of the chlorinated ep...
Understanding the supramolecular environment of crystal structures is necessary to facilitate designing molecules with desirable properties. A series of 12 novel 1,3,5-tris(1-phenyl-1H-pyrazol-5-yl)benzenes was used to assess the existence of planar...
2-Cyano-3-(1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)acrylamide (3) was synthesized in 90% yield from condensation of equimolar equivalents of 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde (1) and 2-cyanoacetamide (2) in boiling ethanol unde...
The title compound (Z)-4-[2-(3,4-difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one 4 was synthesized by the reaction of ethyl 2-[2-(3,4-difluorophenyl)hydrazono]-3-oxobutanoate 3 with hydrazine hydrate. The diazotization of 3,4-difluoroaniline,...
A series of novel pyrazole amide derivatives 3a–3p which take TMV PC protein as the target has been designed and synthesized by the reactions of 5-chloro-1-aryl-3-methyl-1H-pyrazole-4-carboxylic acids with 5-amino-1-aryl-1H-pyrazole-4-carbonitriles....
We review here new advances in the synthesis and investigation of iron(II) coordination compounds with tris(pyrazol-1-yl)methane and its derivatives as ligands. The complexes demonstrate thermally induced spin crossover accompanied by thermochromism....
The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in...
Cyclin-dependent kinase 2 (CDK2) has been garnering considerable interest as a target to develop new cancer treatments and to ameliorate resistance to CDK4/6 inhibitors. However, a selective CDK2 inhibitor has yet to be clinically approved. With the...
Novel 4-[(2-hydroxy-4-pentadecylbenzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one was prepared via condensation of 2-hydroxy-4-pentadecylbenzaldehyde (1) with 4-amino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (2) in ethanol/a...
In this work, the title compound was synthesized via the reaction of an aryl-substituted pyrazole with potassium tetrachloroplatinate, followed by the reaction of the postulated intermediate chloro-bridged dimer with a pyrazole-containing 1,3-diketon...
The tripodal ligand N,N-bis-(3-carbomethoxy-5-methylpyrazol-1-yl)methyl aniline (2) has been prepared by the condensation of aniline with two equivalents of N-hydroxymethyl[3-carbomethoxy-5-methyl]pyrazole. The molecule consists of two structurally a...
The ligandless palladium-catalyzed Heck reaction of 4-ethenyl-3-methoxy-1-phenyl-1H-pyrazole and 2-([1,1′-biphenyl]-4-yl)-5-bromo-3,3-dimethyl-3H-indole gave the previously unreported 2-([1,1′-biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-...
A series of pyrazole carboxamide and isoxazolol pyrazole carboxylate derivatives were designed and synthesized in this study. The structures of the compounds were elucidated based on spectral data (infrared, proton nuclear magnetic resonance and mass...
The reaction of a 1:1 mixture of 3-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (1) and 2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (2) in anhydrous ethanol containing piperidine as a catalyst under reflux for 4 h gave (2Z,5Z)-5-((3...
5H-Chromeno[2,3-b]pyridines are important compounds with industrial, biological, and medicinal properties. In this short note, the multicomponent reaction of salicylaldehyde, malononitrile dimer, and 2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazo...
The present review presents an overview of antitumor pyrazoles of natural or bioinspired origins. Pyrazole compounds are relatively rare in nature, the first ones having been reported in 1966 and being essentially used as somniferous drugs. Cytotoxic...
As a consequence of one-pot, three-component reaction of trans-2-benzoyl-3-(4-nitrophenyl)aziridine with 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and ammonium acetate, 2-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophenyl)-4-ph...
Synthesis of novel pyrazole-fused heterocycles, i.e., dihydro-1H- or 2H-oxepino[3,2-c]pyrazoles (6 or 7) from 4-allyloxy-1H-pyrazoles (1) via combination of Claisen rearrangement and ring-closing metathesis (RCM) has been achieved. A suitable catalys...
A simple method for the synthesis of a pyrazolyl thiazole derivative containing a piperonal moiety was developed. Thus, 2-{5-(1,3-benzodioxol-5-yl)-1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-4,5-dihydro-1H-pyrazol-3-yl}pyrazine was synthesized using mic...
A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol (2), has been synthesiz...
Leishmaniases are among the most impacting neglected tropical diseases. In attempts to repurpose antimalarial drugs or candidates, it was found that selected 1,2,4-trioxanes, 1,2,4,5-tetraoxanes, and pyrazole-containing chemotypes demonstrated activi...
In this paper, an efficient synthetic route from pyrazole-chalcones to novel 6-aryl-5-hydroxy-2-phenylpyrano[2,3-c]pyrazol-4(2H)-ones as 3-hydroxyflavone analogues is described. The methylation of 5-hydroxy-2,6-phenylpyrano[2,3-c]pyrazol-4(2H)-one wi...
(1) Background: different previously synthesized pyrazoles and imidazo-pyrazoles showed interesting anti-angiogenic action, being able to interfere with ERK1/2, AKT and p38MAPK phosphorylation in different manners and with different potency; (2) Meth...
Leishmaniasis is a neglected disease responsible for about 56,000 deaths every year. Despite its importance, there are no effective, safe and proper treatments for leishmaniasis due to strain resistance and/or drug side-effects. In this work we repor...
Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacentnitrogen- containing heterocycles, represent two important classes of biologically active compounds. Certain derivatives of these scaffolds play an important role i...
Prior to 2021, 4-bromo-1H-pyrazole (published in 1999) was the only structurally characterized 4-halogenated-1H-pyrazole in the Cambridge Crystallographic Data Center (CCDC). The structures of 4-chloro-1H-pyrazole and 4-fluoro-1H-pyrazole were publis...
The pyrazole ring represents a widely applied chemical scaffold in medicinal chemistry research and we have observed that the physicochemical and biological features of highly substituted pyrazoles can be successfully improved by their encapsulation...
The reaction of equimolar quantities of 3-(1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst u...
Treatment of perchloro-7H-cyclopropano[a]acenaphthylene 1 with hydrazine hydrate in DMF at ca. 80 °C gives the new 3,4,5,6,7,8,9-heptachlorophenaleno[1,9-bc]pyrazole 2 in 69% yield. This compound is the first example of a phenalene fused pyrazole.
4-(4-Chlorophenyl)-2-(5-(4-fluorophenyl)-3-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole (4) and 4-(4-fluorophenyl)-2-(5-(4-fluorophenyl)-3-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-4,5-dihydro-1H-...
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