Showing papers on "Pyrazoline published in 2010"
TL;DR: 2-acetyl benzimidazole was allowed to react with substituted aromatic aldehydes to get desired intermediate chalcones and was found to be the most active candidate of the series and selected for further evaluation at five dose level screening.
146 citations
TL;DR: Eighteen new 1-N-substituted-3,5-diphenyl-2-pyrazoline derivatives have been synthesized and cyclooxygenase inhibitory activities have been evaluated, showing that all of new derivatives are not endowed with improved anti-inflammatory activity against COX-1, but some of them showed a good activity againstCOX-2.
103 citations
TL;DR: A novel class of nonsteroidal pyrazoline antagonists of the mineralocorticoid receptor (MR) that show excellent potency and selectivity against other nuclear receptors that were discovered by incorporation of a single carboxylate moiety.
Abstract: We have discovered a novel class of nonsteroidal pyrazoline antagonists of the mineralocorticoid receptor (MR) that show excellent potency and selectivity against other nuclear receptors. Early analogues were poorly soluble and had a propensity to inhibit the hERG channel. Remarkably, both of these challenges were overcome by incorporation of a single carboxylate moiety. Structural modification of carboxylate-containing lead R-4g with a wide range of substituents at each position of the pyrazoline ring resulted in R-12o, which shows excellent activity against MR and reasonable pharmacokinetic profile. Introduction of conformational restriction led to a novel series characterized by exquisite potency and favorable steroid receptor selectivity and pharmacokinetic profile. Oral dosing of 3S,3aR-27d (PF-3882845) in the Dahl salt sensitive preclinical model of salt-induced hypertension and nephropathy showed blood pressure attenuation significantly greater than that with eplerenone, reduction in urinary albumin, and renal protection. As a result of these findings, 3S,3aR-27d was advanced to clinical studies.
88 citations
TL;DR: Ten novel 3,5-diaryl pyrazolines were synthesized and investigated for their monoamine oxidase inhibitory property and were found to be reversible and selective inhibitor for either one of the isoform (MAO-A or MAO-B).
68 citations
TL;DR: This is the first instance wherein chromeno-pyrazolines have been found to be active antimalarial agents and further exploration and optimization of this new lead could provide novel, antimalaria molecules which can ward off issues of cross-resistance to drugs like chloroquine.
68 citations
TL;DR: In this article, a coumarin-based chromophores with azo and pyrazoline moieties were synthesized and their structures and properties elucidated using spectroscopy.
54 citations
TL;DR: The new compounds screened for analgesic and anti-inflammatory activity and most of them showed good activity comparable with that of standard drugs Pentazocin and Diclofinac sodium respectively.
54 citations
TL;DR: 3,5-Diaryl pyrazolines analogs synthesized and evaluated for their monoamine oxidase (MAO) inhibitory activity were found reversible and selective towards MAO-A with selectivity index in the magnitude of 10(3)-10(5), and the theoretical (K(i)) values obtained were in congruence with their experimental values.
52 citations
TL;DR: A Cu(i)-responsive fluorescent probe is prepared and characterized, constructed using a large tetradentate, 16-membered thiazacrown ligand and 1,3,5-triaryl-substituted pyrazoline fluorophores, and observed fluorescence increase was selective towards Cu( i) over a broad range of mono- and divalent transition metal cations.
Abstract: We have prepared and characterized a Cu(I)-responsive fluorescent probe, constructed using a large tetradentate, 16-membered thiazacrown ligand ([16]aneNS3) and 1,3,5-triaryl-substituted pyrazoline fluorophores. The fluorescence contrast ratio upon analyte binding, which is mainly governed by changes of the photoinduced electron transfer (PET) driving force between the ligand and fluorophore, was systematically optimized by increasing the electron withdrawing character of the 1-aryl-ring, yielding a maximum 50-fold fluorescence enhancement upon saturation with Cu(I) in methanol and a greater than 300-fold enhancement upon protonation with trifluoroacetic acid. The observed fluorescence increase was selective towards Cu(I) over a broad range of mono- and divalent transition metal cations. Previously established Hammett LFERs proved to be a valuable tool to predict two of the PET key parameters, the acceptor potential (E(A/A−) and the excited state energy ΔE00, and thus to identify a set of pyrazolines that would best match the thermodynamic requirements imposed by the donor potential E(D+/D) of the thiazacrown receptor. The described approach should be applicable for rationally designing high-contrast pyrazoline-based PET probes selective towards other metal cations.
50 citations
01 Jan 2010
TL;DR: Aldol condensation reaction between 3-indolaldehyde 1 and 4-methoxyacetophenone 2 afforded chalcone compounds as mentioned in this paper, and the structures of all the compounds were confirmed by microanalyses and various spectral data.
Abstract: Aldol condensation reaction between 3-indolaldehyde 1 and 4-methoxyacetophenone 2 afforded chalcone compounds 3. This compound was reacted with some different reagents such as hydrazine hydrate, phenyl hydrazine, thiosemicarbazide, hydroxylamine, ethyl cyanoacetate, urea and thiourea to give pyrazolines 4a, 4b, 5a, 5b, 6, oxazoline 7, Michael adduct 8, pyranone 9, and oxo 14a and thiopyrimidine derivatives 14b, respectively. The structures of all the compounds were confirmed by microanalyses and various spectral data. Some of the synthesized new compounds were screened against antitumor and antimicrobial activity. (Journal of American Science. 2011;7(1):57-66). (ISSN: 1545-1003).
41 citations
TL;DR: A number of new 2,6-didisubstituted pyrimidine, pyrazoline, and pyran derivatives were synthesized starting from their chalcone derivative and displayed different degrees of antimicrobial activity against Bscillus subtilis, Pseudomonas aeruginosa, and Streptomyces species.
Abstract: A number of new 2,6-didisubstituted pyrimidine, pyrazoline, and pyran derivatives were synthesized starting from their chalcone derivative. The synthesized compounds displayed different degrees of antimicrobial activity against Bscillus subtilis (Gram-positive), Pseudomonas aeruginosa (Gram-negative), and Streptomyces species (Actinomycetes).
TL;DR: Some substituted 3,5-diphenyl-2-pyrazoline-1-carboxamide derivatives were synthesized from appropriate substituted 1,3-diminear poly(2-en-1)-one (chalcone) on reaction with semicarbazide hydrochloride as discussed by the authors.
Abstract: Some substituted 3,5-diphenyl-2-pyrazoline-1-carboxamide derivatives were synthesized from appropriate substituted 1,3-diphenylprop-2-en-1-one (chalcone) on reaction with semicarbazide hydrochloride. The final compounds were structurally elucidated on the basis of IR, 1H-NMR & mass spectral data and microanalyses. The final compounds were evaluated for anticonvulsant activity by the maximal electroshock seizure (MES) method. The neurotoxicity was determined by rotorod toxicity test on male albino mice. The preliminary results showed that all of the tested compounds were protective against MES at 100-300 mg/kg dose levels. The compounds numbered 4d-4e, 4j-4k, and 4m-4t were most protective against MES even at 30 mg/kg dose levels.
TL;DR: In this paper, pyrazoline optical materials were synthesized and characterized using 1 H, 13 C NMR and HRMS; the thermal, optical and electrochemical properties of the compounds were also investigated.
TL;DR: A series of novel 1,3,5-triaryl pyrazoline derivatives has been synthesized by the reaction of chalcone and 3-chloro-6-hydrazinylpyridazine in 47-82% yields.
Abstract: A series of novel 1,3,5-triaryl pyrazoline derivatives has been synthesized by the reaction of chalcone and 3-chloro-6-hydrazinylpyridazine in 47–82% yields. The structures of compounds obtained were determined by IR, 1H NMR and HRMS spectra. Representatively, the spatial structure of compound 3d was determined by using X-ray diffraction analysis. Absorption and fluorescence spectral characteristics of the compounds were investigated in CHCl3 by UV–vis absorption and emission spectra. The results showed that the absorption maxima of the compounds vary from 332 to 342 nm depending on the group bonded to benzene rings. The maximum emission spectra of compounds in CHCl3 are dependent on groups in benzene ring in which a strong electron-donating group in benzene ring such as methoxyl group on C3 position of pyrazoline made the emission wavelength of 3e, 3f and 3g red shifted than that of compounds 3b, 3c and 3d with chlorine group. The intensity of absorption and fluorescence was also correlated with substituent on two aryl rings. In addition, the absorption spectra of these compounds change very little with increasing solvent polarity.
TL;DR: The synthesis of a new series of 1-[(benzazole-2-yl)thioacetyl]-3,5-diaryl- 2-pyrazoline derivatives was obtained and their antifungal activities against Candida albicans, Candida glabrata,candida utilis, CandIDA tropicalis,Candida krusei, and Candida parapsilosis were investigated.
Abstract: The synthesis of a new series of 1-[(benzazole-2-yl)thioacetyl]-3,5-diaryl-2-pyrazoline derivatives was obtained by reacting 1-(chloroacetyl)-3,5-diaryl-pyrazolines with 2-mercaptobenzimidazole/benzoxazole/benzothiazole. The chemical structures of the compounds were elucidated by (1)H-NMR, (13)C-NMR, and FAB(+)-MS spectral data. Their antifungal activities against Candida albicans, Candida glabrata, Candida utilis, Candida tropicalis, Candida krusei, and Candida parapsilosis were investigated. A significant level of activity was observed.
TL;DR: Chalcone derivative 3 was synthesized via the base catalyzed Claisen-Schmidt condensation and was used as a precursor for synthesizing pyrazoline 11, isoxazoline 12,Pyrazoline carbothioamide 13, 5,6-dihydropyrimidine-2-(1H)-thione 14 and aminopyridinecarbonitrile derivative 15 and exhibited promising molluscicidal activities.
TL;DR: The results suggest that the N,N-disubstituted dithiocarbamate moiety of pyrazoline derivatives may have therapeutic antidepressant potential.
Abstract: Many studies have shown that pyrazoline derivatives have therapeutic potential as antidepressant drugs. In this study, we aimed to investigate the antidepressant-like effect of eight new 1-[(N,N-disubstituted thiocarbamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2-pyrazolines that have previously been synthesized in our laboratory. Antidepressant-like activity was investigated in mouse forced swimming test (FST). Drug-induced effects on motor function were also tested by using digitized motor activity monitoring system. Shortened immobility time in FST was accepted as indicator of antidepressant-like activity. Results showed that three of eight pyrazoline compounds (1b, 1d, 1g) significantly shortened immobility time compared with control. Compound 1b was found to be more effective in FST than were clomipramine and tranylcypromine, used as reference antidepressant drugs. This compound also significantly increased horizontal motor activity, like clomipramine, compared with control mice. These results suggest that the N,N-disubstituted dithiocarbamate moiety of pyrazoline derivatives may have therapeutic antidepressant potential.
TL;DR: A series of novel 5-aryl-1-arylthiazolyl-3-ferrocenyl-pyrazoline derivatives has been synthesized by the reaction of ferroceneyl chalcone and thiosemicarbazide in 48-90% yields using IR, 1H NMR and HRMS and X-ray diffraction analysis as discussed by the authors.
Abstract: A series of novel 5-aryl-1-arylthiazolyl-3-ferrocenyl-pyrazoline derivatives has been synthesized by the reaction of ferrocenyl chalcone and thiosemicarbazide followed by the reaction with 2-bromo-1-arylethanone in 48–90% yields. The compounds were characterized using IR, 1H NMR and HRMS and X-ray diffraction analysis. The absorption and fluorescence characteristics of the compounds were investigated in dichloromethane, chloroform and tetrahydrofuran. The results showed that the absorption maxima of the compounds vary from 316 to 347 nm depending on the group bonded to phenylthiazole rings. The electron-donating methoxyl group in phenylthiazole moiety caused red shifts in dichloromethane solution, and the electron-withdrawing chloro group resulted in blue shifts. The absorption maxima of these compounds in tetrahydrofuran were red shift compared with that in dichloromethane and chloroform. The maximum emission spectra of compounds in tetrahydrofuran were also red shift compared with that in dichloromethane.
TL;DR: Some new bioactive fluorine heterocyclic systems containing sulfur and nitrogen as five-membered rings have been derived from the interaction of sulfa drugs with fluorine aromatic aldehyde and/or hexa fluoroacetic anhydride as discussed by the authors.
Abstract: Some more new bioactive fluorine heterocyclic systems containing sulfur and nitrogen as five-membered rings: pyrazoline, imidazole, imidazolopyrimidine, thiazolidinone and 1,2,4-triazole derivatives (3-13) have been synthetically derived from the interaction of sulfa drugs with fluorine aromatic aldehyde and/or hexa fluoroacetic anhydride followed by heterocyclization reactions. Former structures of the targets have been deduced upon the help of elemental and spectral data.. Compounds 7a-f, 10c and 13 could be used as photochemical probe agents for inhibition of Vitiligo diseases, in compare with Nystatin and Nalidixic acid.
Journal Article•
TL;DR: The title compounds (IV) and (V) exhibit good antibacterial, antifungal and insecticidal activities.
Abstract: 4-Methyl-3-acetyl cinnoline used as a precursor to synthesizec some new cinnoline based -chalcones 3a-1. Reaction of chalcone with hydrazine hydrate in acctic acid yields thc cinnoline bascd pyrazoline derivatives 4a-1. The structures of synthesized compounds have bccn confirmed by elemental analysis, IR and NMR spectral studies and evaluated for their antibacterial activity against Bacillus subtilis, Escherichia coli, Staphylococcus aureaus and Klebsiella pneumoniae, antifungal activity against Aspergillus flavus, Fusarium oxysporum, Aspergillus niger and Trichoderma viridae and insecticidal activity against Periplaneta americana.
TL;DR: In this paper, the luminescence properties of the pyrazoline-1,3-diones were investigated and the substituents on pyrazolines were found to have a significant impact on the solid-state luminescent properties.
TL;DR: In this article, 2-Aryl-1H-indole-3-carbaldehyde derivatives underwent Claisen-Schmidt condensation with acetophenone derivatives under microwave irradiation condition compared with the conventional heating to afford excellent yields of trans substituted indolylchalcones which subjected to condensation reaction with phenylhydrazine to afford their indolylspyrazoline analogs.
Abstract: 2-Aryl-1H-indole-3-carbaldehyde derivatives underwent Claisen-Schmidt condensation with acetophenone derivatives under microwave irradiation condition compared with the conventional heating to afford excellent yields of trans substituted indolylchalcones which subjected to condensation reaction with phenylhydrazine to afford their indolylpyrazoline analogs. The antitumor activity of the synthesized compounds was examined and evaluated against human hepatocellular carcinoma cell line (Hep-G2) as well as the half maximal inhibitory concentration (IC50). Most of them showed high potent antitumor activity.
TL;DR: In this article, 3-trifluoromethyl-substituted 4-nitrosopyrazolines and 4-nissopyrazoles were synthesized by a one-pot synthesis from trifluorsyl-containing 1,3-diketones, sodium nitrite in acetic acid, and hydrazines (hydrazine hydrate, methyl hydride).
Abstract: 3-Trifluoromethyl-substituted 4-nitrosopyrazolines and 4-nitrosopyrazoles were prepared by a one-pot synthesis from trifluoromethyl-containing 1,3-diketones, sodium nitrite in acetic acid, and hydrazines (hydrazine hydrate, methylhydrazine). 3-Trifluoromethylpyrazolines can be converted to pyrazoles on heating. The use of phenylhydrazine in these reactions led to the formation of regioisomeric 4-hydroxyimino-5-(trifluoromethyl)pyrazoline. The structure of heterocycles synthesized was established using X-ray diffraction study, 1H and 19F NMR spectroscopy. The obtained products exhibited considerable tuberculostatic activity.
TL;DR: The discovery of novel pyrazoline derivatives as B-Raf (V600E) inhibitors is described and determination of the pharmacokinetic properties of selected inhibitors is also reported.
TL;DR: In this article, the structure of the reaction product from 1,3,5-trinitrobenzene and an excess (i.e., at least four moles) of diazomethane, as found many years ago by Heinke, is shown to be a seven-membered ring-compound condensed with two cyclopropane rings and with one pyrazoline ring.
Abstract: The structure of the reaction product from 1,3,5-trinitrobenzene and an excess (i.e. at least four moles) of diazomethane, as found many years ago by Heinke, is shown to be a seven-membered ring-compound condensed with two cyclopropane rings and with one pyrazoline ring (VII). If 1,3,5-trinitrobenzene is treated with diazomethane in a molar ratio of 1:3, no pyrazoline derivative is formed, but a hitherto unknown “tris-methylene” derivative (VI), containing a seven-membered ring system condensed with two cyclopropane rings. This remarkably stable compound is an intermediate in the reaction with excess of diazomethane. When the molar ratio of the reactants is reduced to 1 : 2 or 1 : 1, the “trismethylene” derivative (VI) results, together with unchanged 1,3,5-trinitrobenzene.
01 Jan 2010
TL;DR: A series of phthalimide derivatives were synthesized and evaluated for their analgesic and anti-inflammatory activity as mentioned in this paper, and the synthesized compounds 3a-j were characterized by IR and NMR spectral data.
Abstract: A series of phthalimide derivatives were synthesized and evaluated for their analgesic and antiinflammatory activity. The synthesized compounds 3a-j were characterized by IR and NMR spectral data. All compounds were screened for their analgesic and antiinflammatory activity. Compounds 3a-j were screened for antiinflammatory activity against carrageenin induced rat paw edema. Except compound 3b all exhibited good antiinflammatory activity, while compounds 3d, 3h and 3j exhibited good analgesic activity when screened against acetic acid induced writhings in mice.
TL;DR: In this article, a series of 3-(phenoxathiin-2-yl)-5-aryl-2 pyrazoline derivatives were synthesized from the reaction of 1-(PN-2]-3-phenyl/(4-chlorophenyl)propenones 1a and 1b with different nitrogen nucleophiles.
Patent•
27 Sep 2010
TL;DR: The present invention is related to pyrazoline dione derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).
Abstract: The present invention is related to pyrazoline dione derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase)
01 Jan 2010
TL;DR: In this article, the authors reported an increase in analgesic, anti-inflammatory and antimicrobial activities attributed to the presence of 4-NO2, 4OH and 4-Cl in phenyl ring at 5position of pyrazoline ring of synthesized compounds.
Abstract: 1H-NMR, mass spectra and elemental analysis. The compounds were screened for analgesic activity by acetic acid induced writhing method and hot plate method, antiinflamatory and antimicrobial activities. The observed increase in analgesic, anti-inflammatory and antimicrobial activities are attributed to the presence of 4-NO2, 4OH and 4-Cl in phenyl ring at 5-position of pyrazoline ring of synthesized compounds. In some cases their activities are equal or more potent than the standard drugs.
TL;DR: In this paper, a simple and efficient procedure for the multigram synthesis of both (±)-trans- and (+)-cis-1-amino-2-(trifluoromethyl)cyclopropane-1 carboxylic acid was developed.
Abstract: A simple and efficient procedure for the multigram synthesis of both (±)-trans- and (+)-cis-1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylic acid was developed. The key step of the synthesis is the addition of 1-diazo-2,2,2-trifluoroethane to methyl 2-[(tert-butoxycarbonyl)amino]acrylate, followed by thermal decomposition of the resulting pyrazoline. Gram quantities of transand cis-1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylic acid were easily prepared from L -serine in one synthetic run.