Showing papers on "Pyrazole published in 2010"
TL;DR: Thiazole 3 and pyrazolo[1,5-a]pyrimidine 21 b were found to exhibit the most potent in vitro antifungal activity with MICs against A. fumigatus and F. oxysporum.
323 citations
TL;DR: Compound 3-(3,4-dimethylphenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (C5) displayed the most potent EGFR inhibitory activity, which would be a potential anticancer agent.
240 citations
TL;DR: In this paper, the authors discuss the development, unique activity, and high selectivity of nano-organocatalysts for microwave-assisted Paal-Knorr reaction, aza-Michael addition, and pyrazole synthesis.
201 citations
TL;DR: Several novel compounds synthesized from a Claisen-Schmidt reaction of 3-aryl-1-phenylpyrazol-4-carboxaldehydes 4 with several acetophenone derivatives were screened by the US National Cancer Institute for their ability to inhibit 60 different human tumor cell lines.
192 citations
182 citations
TL;DR: Interestingly all the synthesized compounds exhibited good antibacterial and antifungal activity (except 2a-c, 6a, 8, 9a).
134 citations
TL;DR: In this paper, a number of new solvates containing pyrazole (Pz) and imidazole (Iz) as ligands, of the general formula M(ligand)n(anion)2 is reported.
Abstract: A number of new solvates containing pyrazole (Pz) and imidazole (Iz) as ligands, of the general formula M(ligand)n(anion)2 is reported. In these compounds M = Mg, Mn, Fe, Co, Ni, Cu, Zn and Cd, the anions are ClO4− and BF44−, and n is usually 6; n = 4 in the case of the Cu compounds and for Zn in combination with Iz.
The compounds are characterized and identified by chemical analysis and physical measurements.
With the aid of ligand-field spectra in combination with X-ray powder patterns, octahedrally coordinated metal ions are found in compounds of stoichiometry M(ligand)6(anion)2. Both Pz and Iz are placed in the spectro-chemical and nephelauxetic series. The spectrochemical series appears to be (with increasing Dq): CH3CN NH3 > Iz > Pz > en.
The magnetic moments for the transition-metal compounds fall within the range usually observed for octahedrally coordinated ions. Both paramagnetic resonance measurements and the deviation of the magnetic moments from the spin-only value, indicate a considerable amount of covalency in the metal-ligand bond.
Infrared spectroscopy evidently shows pure ionic ClO4− and BF4− for all solvates, except those of Cu(II) where the anions are coordinated to the metal ion. Except for the N-H modes, no large shifts occur in the ligand infrared absorptions with respect to the free ligand. Compared with the gaseous ligands, the N-H stretch in the solvates is decreased, whereas the bending modes are increased in frequency. This is attributed to - weak - hydrogen bonding with the anions in the lattice of these solvates.
Metal-ligand stretching frequencies for both ligands occur in the 165-330 cm−1 range, and follow the Irving-Williams sequence of metal ions.
133 citations
TL;DR: In this article, the condensation of l-(hydroxymethyl)pyrazole (1a) and l(hydroxyl)3,5-dimethyl pyrazole(1b) with the following amines (products given in parentheses): ethylamine (2a and 2b), aniline (3a and 3b), N,N′-dimdimethyl- l, 2-ethanediamine (4a and 4b), 1,2-ethane), diethylenetriamine (7a
Abstract: Procedures are described involving the condensation of l-(hydroxymethyl)pyrazole (1a) and l-(hydroxymethyl)-3,5-dimethylpyrazole (1b) with the following amines (products given in parentheses): ethylamine (2a and 2b), aniline (3a and 3b), N,N′-dimethyl- l,2-ethanediamine (4a and 4b), 1,2-ethanediamine (6a and 6b), diethylenetriamine (7a and 7b), triethylenetetramine (8a and 8b) and ammonia (9a and 9b). All amine hydrogens are completely substituted by pyrazol-1-ylmethyl groups (compounds 2a-9a) or (3,5-dimethylpyrazol-1-yl)methyl groups (compounds 2b-9b with yields being better than 90%.
123 citations
TL;DR: In this article, a one-pot multicomponent reaction involving the use of an aldehyde, a cyanoacid derivative, and the Bestmann-Ohira reagent (BOR) was developed for the synthesis of substituted phosphonyl pyrazoles.
Abstract: A new one-pot multicomponent reaction involving the use of an aldehyde, a cyanoacid derivative, and the Bestmann-Ohira reagent (BOR) is developed for the synthesis of substituted phosphonyl pyrazoles.
106 citations
TL;DR: Compounds containing the fused pyrazolo[4,3-c]quinoline motifs emerged as potent anti-angiogenic compounds, which also had the ability to inhibit the growth of human breast and cervical carcinoma cells in vitro.
102 citations
TL;DR: A series of novel 2,4-disubstituted thiazole derivatives containing substituted pyrazole moiety showed significant antibacterial activity against all tested microorganisms.
TL;DR: The dioxovanadium complexes A2(3,5-Me2Hpz)3)A4 )( 1) (pz = pyrazolyl), A2A3C(pz), (2), (VO2{HB(1-pyrazolyls)3}) (3) and (VO 2{HC(methane) 3}) as discussed by the authors, bearing pyrazole or scorpionate ligands, were obtained by reaction of triethyl vanadate (VOA3) with hydrotris (3, 5-
Abstract: The dioxovanadium(V) complexes A2(3,5-Me2Hpz)3)A4 )( 1) (pz = pyrazolyl), A2A3C(pz)3}) (2), (VO2{HB(3,5-Me2pz)3}) (3) and (VO2{HC(pz)3})A4 )( 4), bearing pyrazole or scorpionate ligands, were obtained by reaction of triethyl vanadate (VOA3) with hydrotris(3,5-di- methyl-1-pyrazolyl)methane (HC(3,5-Me2pz)3 )o r 3,5-diA (3,5-Me2Hpz; 1), lithium tris(1- pyraAfonate {LiA3C(pz)3), 2}, potassium hydrotris(3,5-dimethyl-1-pyrazolyl)borate {K(HB(3,5-Me2pz)3), 3} and hydrotris(1-pyrazolyl)- methane (HC(pz)3, 4), respectively. Treatment of (VOA3) with potassium hydrotris(1-pyrazolyl)bo- rate {K(HB(pz)3)} led to the mixed h 3 -tris(pyrazolyl)-
TL;DR: All new synthesized compounds were evaluated as antimicrobial agents; some of them exhibited promising activities.
TL;DR: The isolated compounds were characterized by their physical properties, elemental analysis, IR-, MS (EI)- and NMR-spectroscopy and the cytotoxic effect of these complexes against the fast growing head and neck squamous carcinoma cells SQ20B and SCC-25 has been studied.
TL;DR: Three series of novel pyrazole derivatives 2-6 were synthesized via two step procedure that utilizes hydrazonoyl chlorides 1a-d and enaminones 3a-D and 5 a-d, respectively as starting materials and revealed that the mechanism of action of the anti cancer activities of all the tested compounds is topoisomerase I inhibitor.
TL;DR: In this article, the N-arylation reactions of imidazoles and aromatic amines with arylboronic acids in methanol at room temperature under base-free conditions were investigated.
TL;DR: Three of the 12 tested compounds showed moderate antitumor activity, one of them being chosen for the 5-dose assay and presented logGI(50) values up to -5.75.
TL;DR: A series of novel oxime-containing pyrazole derivatives were synthesized by the reaction of ethyl 3-phenyl-1H-pyrazole-5-carboxylate derivatives and 2-bromo-1-phenylethanone followed by the Reaction with hydroxylamine hydrochloride and inhibition of proliferation was observed in A549 lung cancer cell after compound treatment.
TL;DR: The most active of the series is the compound 13, N1-thiocarbamoyl-3-(fur-2'-yl)-5-(4'-fluoro-phenyl)-4,5-dihydro-(1H)-pyrazole, with IC(50) 2.75+/-0.81muM value and selectivity ratio of 25, which is the best candidate for further investigations.
TL;DR: Heterobiaryl analogues of the antituberculosis drug PA-824, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility.
Abstract: Recently described biphenyl analogues of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more...
TL;DR: A series of chalcones and pyrazoles was prepared to investigate their potential activity as Angiotensin I-Converting Enzyme (ACE) inhibitors and, among tested compounds, chalcone 7 exerted the highest activity.
TL;DR: A novel synthesis of 4-oxo-4H-pyrano[2,3-c]pyrazole could be achieved via reacting 3-methyl-2-pyrazolin-5-one with a mixture of cyanoacetic acid and acetic anhydride.
Abstract: Pyrano[2,3-c]pyrazoles are obtained via mixing ethyl acetoacetate, hydrazine hydrate, aldehydes or ketones and malononitrile in the absence of solvent. These same products were also obtained by reacting arylidenemalononitriles 3 with 3-methyl-2-pyrazolin-5-ones. NOE difference experiments confirmed that these products exist solely in the 2H form. Similar treatments of 3-amino-2-pyrazolin-5-one with arylidene-malononitrile afforded adduct 6. Similarly mixing ethyl cyanoacetate, hydrazine hydrate, aldehydes, with malononitrile gave the same product 6. A novel synthesis of 4-oxo-4H-pyrano[2,3-c]pyrazole (8) could be achieved via reacting 3-methyl-2-pyrazolin-5-one with a mixture of cyanoacetic acid and acetic anhydride. Similar treatment of 3-aminopyrazole 11 with the benzylidene-malononitrile produced the pyrazolo[2,3-a]pyrimidines 12a,b.
TL;DR: An ultrasound-assisted preparation of a series of novel 3,5-diaryl-4, 5-dihydro-1H-pyrazole-1-carboximidamides that proceeds via the efficient reaction of chalcones with aminoguanidine hydrochloride under clean conditions is described.
TL;DR: A series of new alpha,beta-unsaturated conjugated ketones containing ferrocenyl pyrazole unit were synthesized and fully characterized by IR and NMR spectroscopy and exhibited a better cytotoxic activity in the cell growth inhibition of K562 cell lines in comparison with cisplatin as a reference compound.
TL;DR: All tested compounds showed anti-estrogenic properties equipotent or superior to the reference drug, letrozole.
TL;DR: Pyrazole carboxylic acid derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide (inhibitor 1) and newly synthesized amides indicated that the new derivatives inhibit CA isoenzymes and they are more potent inhibitors than the parent inhibitor 1 and AAZ.
TL;DR: Ternary systems of celecoxib, poly(vinyl pyrrolidone) (PVP) and meglumine were studied for molecular interactions responsible for enhanced drug stability and solubility in amorphous form and molecular interaction between the three species was found to be the potential cause for enhanced stability andsolubility.
Abstract: Stabilization of the amorphous form of a drug is conferred by additives that interact with it at the molecular level. Ternary systems of celecoxib, poly(vinyl pyrrolidone) (PVP) and meglumine were studied for molecular interactions responsible for enhanced drug stability and solubility in amorphous form. Meglumine was found to lower the glass transition temperature (T g ) of the drug due to its plasticization effect. However, the presence of PVP masked its destabilizing effect and provided net anti-plasticization to the celecoxib-PVP-meglumine (7:2:1 w/w) ternary amorphous system. Positive deviation of the experimentally determined T g m ι x value for this composition, from those predicted by the Gordon-Taylor/Kelley-Bueche equation, inferred molecular interaction between the three species, which was also supported by band shifts from their Fourier-transform infra-red (FTIR) spectra. Further, shift of differential scanning calorimetry (DSC) melting endotherms of celecoxib in its amorphous systems from those observed for crystalline celecoxib confirmed the complexation between these components, which was also substantiated by molecular modelling studies that showed H-bonding of -S=O, 2-N of the pyrazole ring and -C-F groups of celecoxib with -O-H group of meglumine. These molecular interactions of amorphous celecoxib with meglumine were found to be the potential cause for enhanced stability and solubility of the celecoxib-PVP-meglumine ternary system.
TL;DR: The ability of nine new synthesized compounds to inhibit Hepatitis C Virus and Subacute Sclerosing Panencephalitis (SSPE) due to structural similarity between ribavirin and some of the newly synthesised compounds were they contain triazoles and its bioisosters is demonstrated.