Showing papers on "Pyrazoline published in 2013"
TL;DR: The review is a gist of latest work done describing the pharmacological aspects and potential of pyrazoline ring.
Abstract: Pyrazoline is an important five membered nitrogen heterocycle, which has been extensively researched upon. The ring is quite stable and has inspired chemists to carry out various structural variations in the ring. This has propelled the development of distinct pyrazolines with an array of pharmacological activities viz. anti-inflammatory, analgesic, antimicrobial, anticancer, antidepressant etc. The review aims at highlighting this pharmacological diversity of pyrazolines. The review is a gist of latest work done describing the pharmacological aspects and potential of pyrazoline ring.
120 citations
TL;DR: DNA binding and in silico studies indicated quite good binding with DNA; requirements for good anticancer drugs.
Abstract: Background: Over the last few decades, metal-based drugs, particularly cisplatin and its analogs have been used for the treatment of various cancers. Currently, scientists are developing other metal complexes as anticancer agents to eliminate the toxicity associated with platinum drugs. Results: Claisen-Schmidt condensation was used to synthesize the pyrazoline-based ligand; (5-(4-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide), followed by the synthesis of its complexes with copper(II), nickel(II) and iron(III) metal ions. DNA binding and in silico studies indicated quite good binding with DNA; requirements for good anticancer drugs. Conclusion: DNA binding constants for ligand, copper, nickel and iron complexes were 1.42 × 104, 3.16 × 104, 5.82 × 105 and 6.72 × 105 M-1, respectively, indicating strong binding with DNA. All the reported compounds were slightly hemolytic towards rabbit red blood corpuscles and exhibited moderate activities against MCF-7 cancer cell lines.
112 citations
TL;DR: A new series of N-acetyl and N-formyl-pyrazoline derivatives 6 and 7-8 showed remarkable antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.13 to 0.99 μM.
108 citations
TL;DR: A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO(4))(2) complex of an N,N'-dioxide ligand, which is so far the sole catalytic synthesis of spiro-pyrazoline-Oxindole derivatives.
94 citations
TL;DR: Two groups of coumarin-pyrazoline hybrids were synthesized and compound 9c which possessed the highest cytotoxicity proved to have weak enzyme inhibitory activity against PI3K (p110α/p85α).
86 citations
TL;DR: The screening of antitrypanosomal and antiviral activities of 5-(3-naphthalen-2-yl-5-aryl-4,5-dihydropyrazol-1-yl)-thiazolidine-2,4-diones was carried out with the promising influence of the mentioned compounds on Trypanosoma brucei, but minimal effect on SARS coronavirus and influenza types A and B viruses.
82 citations
TL;DR: In this paper, a pyrazoline derivate was designed and synthesized and its structure was confirmed by single crystal X-ray diffraction and its photophysical properties were studied by absorption and fluorescence spectra.
70 citations
TL;DR: Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
62 citations
TL;DR: Two series of novel isosteviol-fused pyrazoline and pyrazole derivatives were facilely synthesized via intramolecular 1,3-dipolar cycloaddition and condensation reaction, respectively and exhibited noteworthy cytotoxic activities.
61 citations
TL;DR: A novel series of pyrazoline amidoxime and pyrazoly-1,2,4-oxadiazole of pharmacological significance and new compounds screened for their in vitro antioxidant, antimicrobial and antiinflammatory activities were synthesised.
54 citations
TL;DR: Five new series of imidazo[1,2-a]pyridines carrying biologically active pyrazoline, cyanopyridone and pyrimidine-2-thione systems showed potent anticonvulsant activity without displaying any toxicity.
TL;DR: It is proposed that VdW's radii of the substitution (bulkiness) in ring B determine the potency of phenyl carbamates.
TL;DR: In this paper, 3-phenyl-5-aryl-1-thiocarbamoyl-2-pyrazolines with 2-bromopropionic acid, maleic anhydride, N-arylmaleimides, and aroylacrylic acids have been synthesized.
TL;DR: The new fluorescent probe, probe 3, was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting glutathione among biological thiols in aqueous media without interference from some biologically relevant analytes.
Abstract: A new fluorescent probe, N-(4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl)-2,4-dinitrobenzenesulfonamide (probe 3), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting glutathione among biological thiols in aqueous media. Probe 3 is a nonfluorescent compound. On being mixed with biothiols under neutral aqueous conditions, the 2,4-dinitrobenzenesulfoyl moiety can be cleaved off by glutathione, and the blue emission of the pyrazoline at 464 nm is switched on, with a fluorescence enhancement of 488-fold for glutathione. Furthermore, probe 3 was highly selective for glutathione without interference from some biologically relevant analytes. The detection limit of glutathione was 4.11 × 10−7 M. The emission of the probe is pH independent in the physiological pH range. Moreover, the probe can be used for fluorescent imaging of cellular glutathione and can be used for detecting glutathione in calf serum.
TL;DR: Results suggested that derivative 7 could inhibit the proliferation of colorectal cancer cells through inhibition of cell cycle progression and induction of apoptosis, and will facilitate the design of potent novel benzochalcones as anticancer agents.
TL;DR: Generally, the 4-unsubstitutedphenylpyrimidine derivatives 5a-h were more active than their 4-chlorophenylpyridine analogs 6 a-h, and showed high activity against three of the cell lines.
TL;DR: A new pyrazoline derivative was designed and synthesized that can be used to determine Fe(3+) ion with high selectivity among a series of cations in tetrahydrofuran and even in aqueous tetrahYDrofurans.
TL;DR: 3-trifluoromethylpyrazoles were found to be the most effective agents and rationalize this anti-inflammatory activity, docking experiments molecular dynamics simulations were performed to study the ability of these compounds to bind into the active site of the COX-2 enzyme.
TL;DR: The synthesis and anti-tumor activity screening of new steroidal derivatives (4-18) containing pharmacologically attractive pyrazoline moieties are performed and the most effective anticancer compound 9 was found to be active with IC50 value of 10.6 μM.
TL;DR: The new probe is cell-permeable and can be successfully used to image intracellular Zn2+ in living neuron cells and display a good selective fluorescence enhancement over various metal ions.
Abstract: A simple pyrazoline-based highly sensitive fluorescent probe for Zn2+ in aqueous solution and biological Zn2+ detection has been developed The probe displays a good selective fluorescence enhancement (13-fold) for Zn2+ over various metal ions The new probe is cell-permeable and can be successfully used to image intracellular Zn2+ in living neuron cells
TL;DR: Xanthine oxidase (XO) inhibitory and free radical scavenging activities were also figured out with molecular modeling analysis, bearing in mind their possible future for super oxide inhibitor (Gout) therapeutics.
TL;DR: New pyrazoline derivatives were synthesized via the reaction of 1‐(chloroacetyl)‐3‐(2‐furyl)‐5‐aryl‐2‐pyrazolines with sodium salts of N,N‐disubstituted dithiocarbamic acids using a modification of Ellman's spectrophotometric method.
Abstract: In the present study, new pyrazoline derivatives were synthesized via the reaction of 1-(chloroacetyl)-3-(2-furyl)-5-aryl-2-pyrazolines with sodium salts of N,N-disubstituted dithiocarbamic acids. Each derivative was evaluated for its ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) using a modification of Ellman's spectrophotometric method. The compounds were also investigated for their cytotoxic properties using the MTT assay. The most potent AChE inhibitor was found as compound 7 followed by compounds 27 and 17, when compared with eserine. Compounds effective on AChE carry the 2-dimethylaminoethyl moiety, which resembles the trimethylammonium group and the ethylene bridge of acetylcholine. Among all compounds, compound 7 bearing 2-dimethylaminoethyl and 3,4-methylenedioxyphenyl moieties was also found to be the most effective inhibitor of BuChE. The MTT assay indicated that the effective concentration of compound 7 was lower than its cytotoxic concentration.
TL;DR: A series of 5-arylidene-2-(3,5-diaryl-4,5dihydro-1H-pyrazol-1-yl]-5-(2-methoxybenzylidene)-1,3-thiazol-4(5H)-one (3i) was found to show the most potent anticancer activity as mentioned in this paper.
Abstract: A series of 5-arylidene-2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-1,3-thiazol-4(5H)-ones were synthesized and screened for their in vitro antitumor activity against human breast adenocarcinoma cell line (MCF-7). Five of the test compounds exhibited good antitumor activity superior to the reference drug, doxorubicin, with IC50 range 1.4–2.3 μM. Among the test compounds, 2-[3,5-bis(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-(2-methoxybenzylidene)-1,3-thiazol-4(5H)-one (3i) was found to show the most potent anticancer activity.
TL;DR: A previously unknown class of highly substituted pyridazines and pyrazoline-spirooxinoles are easily prepared by an uncatalyzed one-pot three-component approach incorporating a domino SN/condensation/aza-ene addition cyclization reaction sequence.
Abstract: A previously unknown class of highly substituted pyridazines and pyrazoline-spirooxinoles are easily prepared by an uncatalyzed one-pot three-component approach incorporating a domino SN/condensation/aza-ene addition cyclization reaction sequence. 1,1-Dihydrazino-2-nitroethylene (DHNE) which is generated in situ from the nucleophilic substitution (SN) reaction of hydrazine and 1,1-bis(methylthio)-2-nitroethylene (BMTNE), allowed to be condensed with active 1,2-dicarbonyl compounds followed by an intramolecular aza-ene addition cyclization to obtain the titled products depending on the type of 1,2-dicarbonyl. All reactions are easily performed and proceed with high efficiency under very simple and mild conditions without any catalyst and give good yields avoiding time-consuming, costly syntheses, and tedious workup and purification of products.
TL;DR: The pyrazole derivative 5c was found to be the most active member in this screen as evidenced by its ability to exert potential growth inhibitory activity against most of the tested subpanel tumor cell lines with selective influence on leukemia subpanel tumors cell lines.
Abstract: The synthesis of some new (E)-6-[2-(furan-2-yl)ethenyl]-1,2,4-triazin-5-ones directly linked to either pyrazole, pyrazoline, pyrazolidine counterparts, or to substituted thio and hydrazono functionalities is described. Six of the newly synthesized compounds were selected by the National Cancer Institute (NCI) to be evaluated for their in vitro antitumor activity according to the protocol of the NCI in vitro disease-oriented human cells screening panel assay. The results revealed that the pyrazole derivative 5c was found to be the most active member in this screen as evidenced by its ability to exert potential growth inhibitory activity against most of the tested subpanel tumor cell lines with selective influence on leukemia subpanel tumor cell lines (GI50 values 2.01–3.03 μM). Moreover, a comparative study for log GI50 values of both compound 5c and 5-fluorouracil (5-FU) revealed that compound 5c showed higher potency than 5-FU against most of the tested subpanel tumor cell lines. Thus compound 5c could be considered as a suitable lead towards the design of broad spectrum antitumor active agents targeting various human tumor cell lines.
TL;DR: In this paper, a method for the synthesis of 4-(substituted phenyl)-3-(3-substitized phenyl)4H-spiro[isoxazole-5,3′-pyrido[1,2-a]pyrimidine]-2′,4′-dione (3), 3-(4-substantituted pyl) 3,3a-dihydropyrazolo[3,4-d]pyridin-4-(2H)-one (5), 3H-
Abstract: A method is presented for the synthesis of 4-(substituted phenyl)-3-(3-substituted phenyl)4H-spiro[isoxazole-5,3′-pyrido[1,2-a]pyrimidine]-2′,4′-dione (3), 3-(4-substituted phenyl)-3H-isoxazole[3, 4-d]pyrido[1,2-a]pyrimidin-4-(3aH)-one (4) and 3-(4-substituted phenyl) 3,3a-dihydropyrazolo[3,4-d]pyrido[1,2-a]pyrimidin-4-(2H)-one (5) which consists of the conversion of 2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione (1) to chalcones (2) and their 1,3-dipolar cycloaddition with appropriate aldoximes to give spiro compounds and heterocyclization using amines to yield isoxazolines and pyrazolines. All the compounds were screened for their antimicrobial and antitubercular activity.
TL;DR: In this paper, a pyrrole chalcone has been synthesized and characterized using 1H NMR, UV-Vis, FT-IR and Mass spectroscopy.
TL;DR: A new pyrazoline-based probe was synthesized and the structure was determined by using X-ray diffraction analysis to develop a probe that responds to Cu2+ in aqueous medium in “turn-off” fluorescent manner with selectivity and sensitivity.
Abstract: A new pyrazoline-based probe was synthesized and the structure was determined by using X-ray diffraction analysis. The probe responds to Cu2+ in aqueous medium in “turn-off” fluorescent manner with selectivity and sensitivity. Furthermore, the probe could be used for real-time tracking of Cu2+ in Hela cells.
TL;DR: Compound 2e, which is the pyrazoline derivative bearing the 2,5‐dichlorophenyl moiety, can be identified as the most promising agent against Klebsiella pneumoniae and Candida glabrata due to its inhibitory effects on K. pneumoniae.
Abstract: 1-(p-Methylphenyl)-3,5-diaryl-2-pyrazoline derivatives (2a-f) were synthesized via the treatment of 1-(1H-indol-3-yl)-3-aryl-2-propen-1-ones (1a-f) with p-methylphenylhydrazine hydrochloride in hot acetic acid. The structures of these compounds were elucidated by IR, ¹H NMR, and mass spectral data and elemental analysis. These compounds were investigated for their antimicrobial activity. Brine-Shrimp lethality assay was carried out to determine the toxicity of the compounds. Compound 2e, which is the pyrazoline derivative bearing the 2,5-dichlorophenyl moiety, can be identified as the most promising agent against Klebsiella pneumoniae (ATCC 13883) and Candida glabrata (ATCC 36583) due to its inhibitory effects on K. pneumoniae and C. glabrata with a MIC value of 100 µg/mL as a non-toxic agent (LC₅₀ > 1000 µg/mL).
TL;DR: In this paper, a pyrazoline derivative 5-(1′-(4-bromophenyl)-3a′,4′,5′,6′, 6a′-hexahydrocyclopentapyrazoline)-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile (PZ) was used as a fluorescence recognition probe and its photophysical signature in homogeneous and heterogeneous cyclodextrin (CD) environments, in addition to its insertion mechanism inside CD.
Abstract: Time-dependent density functional theory (TD-DFT) calculations and molecular docking analysis provide valuable insights, in addition to experimental evidence, on the newly synthesized pyrazoline derivative 5-(1′-(4-bromophenyl)-3a′,4′,5′,6′,6a′-hexahydrocyclopentapyrazoline)-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile (PZ) as a fluorescence recognition probe and its photophysical signature in homogeneous and heterogeneous cyclodextrin (CD) environments, in addition to its insertion mechanism inside CD. The spectral trends of PZ do not appear to originate only from changes to the solvent polarity, but also indicate hydrogen bonding interactions with a homogeneous medium. The encapsulation of PZ within supramolecular α-, β- and γ-CD hosts was investigated using fluorescence spectroscopic techniques. The results show the formation of both 1 : 1 and 1 : 2 PZ–CD inclusion complexes with β-CD and only a 1 : 1 complex with γ-CD. The measured lifetimes and steady state anisotropy values also show the same trend and reveal the mode of interaction of the probe with the CD moiety. Furthermore, molecular docking studies performed via molecular mechanics methods (MMC) indicate that the pyrazoline moiety of PZ is most likely oriented towards the dip inside the cyclodextrin cavity. Solvent-dependent spectral data using TD-DFT calculations on the optimized ground and excited state structures of PZ were found to correlate well with the experimental findings.