Showing papers on "Pyrazoline published in 2019"
TL;DR: All sulfonamide derivatives studied here can be considered as good candidates to develop novel CAs or AChE inhibitor candidates based on the enzyme inhibition potencies with their low cytotoxicity and tumor selectivity.
98 citations
TL;DR: Docking and molecular modeling study was initiated to validate the attained pharmacological data and provide understandable evidence for the observed anti-inflammatory behavior of the most potent compounds 14b, 15b and 22 through their various interactions with the active site of COX-2 isozyme.
56 citations
TL;DR: The inhibition profile of the new pyrazoline compounds at the receptors was determined and these compounds were effective inhibitor compounds of the human carbonic anhydrase I and II isozymes and of the acetylcholinesterase (AChE) enzyme.
Abstract: In this study, synthesis of ethyl 2-((4-bromophenyl)diazenyl)-3-oxo-phenylpropanoate 1 was carried out and a series of new 3H-pyrazol-3-ones (P1-7) were synthesized from 1 as well as various hydrazines. The obtained yields of the synthesized compounds were moderate (40-70%) and these compounds were confirmed by spectral data. These novel pyrazoline derivatives were effective inhibitor compounds of the human carbonic anhydrase I and II isozymes (hCAs I and II) and of the acetylcholinesterase (AChE) enzyme, with Ki values in the range of 17.4-40.7 nM for hCA I, 16.1-55.2 nM for hCA II, and 48.2-84.1 nM for AChE. In silico studies were performed on the compounds inhibiting hCA I, hCA II, and AChE receptors. On the basis of the findings, the inhibition profile of the new pyrazoline compounds at the receptors was determined.
55 citations
TL;DR: This straightforward protocol exhibits good functional group tolerance and scalability and provides the spiro-pyrazoline-cyclohexadienones.
Abstract: [3 + 2] cycloaddition of para-quinone methides with nitrile imines under mild conditions has been achieved. The corresponding spiro-pyrazoline-cyclohexadienone products were constructed in good to excellent yields (up to 97% yield) with high regioselectivity. This straightforward protocol exhibits good functional group tolerance and scalability and provides the spiro-pyrazoline-cyclohexadienones.
40 citations
TL;DR: In this article, the pyrazoline pyridazine derivative 7-methyl-2-phenyl-4-(3,4,5-trimethoxyphenyl)-2H-pyrazolo[3, 4-d]pyridine (5d) was studied for its interaction with bovine serum albumin (BSA).
Abstract: In this research, the pyrazoline pyridazine derivative 7-methyl-2-phenyl-4-(3,4,5-trimethoxyphenyl)-2H-pyrazolo[3,4-d]pyridazine (5d) was studied for its interaction with bovine serum albumin (BSA). Various spectroscopic techniques along with molecular docking analysis were utilized to understand the mechanism of interaction. The quenching of BSA fluorescence by using investigational drug 5d was the basic principle for the methodology. Spectrofluorometric methods and UV-absorption studies were conducted for exploration of the 5d and BSA binding mechanism. The fluorescence quenching mechanism involved in BSA and 5d interaction was static quenching, and a complex formation also occurred between them. Both enthalpy and entropy attained positive values suggesting involvement of hydrophobic forces in BSA and 5d interaction. The Forster distance of 2.23 nm was calculated by fluorescence resonance energy transfer (FRET). An alteration in BSA secondary structure was proven from the conformational studies of BSA-5d interaction. This binding interaction study provided a basis to comprehend the binding interaction between 5d and BSA. These results provided information about sites of BSA involved in its interaction with 5d.
40 citations
TL;DR: Findings suggest that the proposed PEO-chitosan nanofiber mats could be used for controlled drug release in local chemotherapy treatment for skin cancer.
36 citations
TL;DR: A series of multifunctional pyrazoline based AIEgens were developed for real-time tracking of lipid metabolism, reversibly monitoring intracellular pH in dual-color mode and specific labeling of lipid droplet related protein.
Abstract: Despite the rapid development of organic fluorescent probes for bioimaging and biosensing applications, construction of advanced probes with multiple biological functions by precisely integrating different functionalized elements into a single molecule has rarely been reported. In this contribution, a series of multifunctional pyrazoline based fluorescent probes (Pyr-n, n = 1–5) were designed and synthesized by introducing different aromatic moieties into the pyrazoline core. All Pyr probes exhibited the aggregation-induced emission effect. Thanks to the excellent biocompatibility and suitable lipophilicity, the Pyr probes can stain the lipid droplets (LDs) in living cells with high specificity as well as track the lipid metabolism in Zebrafish embryos. The protonation–deprotonation capability of the diethylamino group enables Pyr-5 to reversibly migrate between LDs and mitochondria, and real-time monitor the intracellular pH change in dual-color mode. The mild reaction between the pentafluorophenyl unit and thiol group makes Pyr probes the ideal probes to “fish out” the proteins associated with LDs in living cells.
36 citations
34 citations
TL;DR: In this paper, all the synthesized compounds were subjected to antibacterial activity evaluation using two Gram+ve and two Gram-ve bacterial strains and were tested for any possible toxic effect to the mammalian cells.
33 citations
TL;DR: The inhibition ofd-alanine-d-Alanine ligase prevents bacterial growth, which makes this enzyme an attractive and viable target in the urgent search for novel effective antimicrobial drugs.
Abstract: The inhibition of D-alanine-D-alanine ligase (Ddl) prevents bacterial growth, which makes this enzyme an attractive and viable target in the urgent search for novel effective antimicrobial drugs. In this work, a series of novel coumarin-linked pyrazoline inhibitors of D-alanine-D-alanine ligase were synthesized and evaluated as inhibitors of Escherichia coli DdlB ligase in order to target resistant strains of bacteria using environmentally benevolent β-cyclodextrin as a supramolecular catalyst via one-pot four component synthesis in water as a green reaction media. All the newly synthesized compounds have been characterized by elemental analysis and various spectroscopic methods. The new procedure has noteworthy advantages including easy work-up, short reaction times, high yields of products and column-free synthesis. The synthesized compounds were evaluated in vitro for their antimicrobial activity. Among the synthesized compounds, namely 3-(5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one (5f) was found to be the most potent D-alanine-D-alanine ligase enzyme inhibitor, with an IC50 value 106 μM, and the compound 3-(5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one (5g) was found to be the second-most potent inhibitor of the DdlB enzyme, with an IC50 value 111 μM against the standard D-cycloserine. In addition, SAR study provided evidence that the –OH, –CH3 and –OCH3 groups at the 4- and 3-position of the coumarins linked to the pyrazolines scaffold increased enzymatic inhibition, while the molecular docking study of most active compounds 5a, 5g, and 5j against DdlB enzyme of E. coli exhibited good binding properties. This work thus highlights the coumarin-linked pyrazoline motif as a very promising tool for the development of novel antimicrobial compounds acting through an interesting bactericidal mechanism of action.
28 citations
TL;DR: In this paper, two pyrazoline-based fluorescent and colorimetric probes have been synthesized and their photophysical properties have been investigated by means of electronic absorption and emission spectroscopy.
Abstract: Two pyrazoline-based fluorescent and colorimetric probes have been synthesized and their photophysical properties have been investigated by means of electronic absorption and emission spectroscopy. The compounds differ from each other by the presence of a phenyl or thiophene end group attached to the α,β-unsaturated ketone. The probes detect sulphite anions in the Michael addition reaction to the α,β-unsaturated ketone with a high selectivity and good sensitivity (7.56 μM for phenyl and 4.87 μM for the thiophene counterpart). Here, the optical response is based on the recovery of triphenylpyrazoline fluorescence, which is largely blue-shifted as compared to weak charge transfer emission of the sensors. This large hypsochromic shift of the emission maximum along with a strong fluorescence enhancement (up to Isulphite/I0 = 43) can be an advantage in terms of the accurate evaluation of the fluorescence intensity ratio. The pyrazoline-based sensor decorated with thiophene is able to detect sulphite species in river water solutions with a good selectivity and sensitivity.
TL;DR: Four new series of aromatic sulfamates were synthesized and investigated for the inhibition of four human (h) isoforms of zinc enzyme carbonic anhydrase and reported derivatives bear 3,5-diarylpyrazoline moieties as spacers between the benzenesulfamate fragment which binds the zinc ion from the active site, and the tail of the inhibitor.
TL;DR: Results indicate that derivatives bearing pyrazoline structure might be considered for further research and scaffold optimization in designing anti-inflammatory drugs and compound 4g might be a promising therapeutic anti‐inflammatory drug candidate.
TL;DR: A scalable, one-pot, enantioselective catalytic synthesis of 2-pyrazolines from beta-substituted enones and hydrazines is described, and the use of an aldehyde to generate a suitable hydrazone derivative of the hydrazine was found to be key for curtailing background reactivity and tuning the catalyst-controlled enantiOSElectivity.
Abstract: A scalable, one-pot, enantioselective catalytic synthesis of 2-pyrazolines from beta-substituted enones and hydrazines is described. Pivoting on a two-stage catalytic Michael addition/condensation strategy, the use of an aldehyde to generate a suitable hydrazone derivative of the hydrazine was found to be key for curtailing background reactivity and tuning the catalyst-controlled enantioselectivity. The new synthetic method is easy to perform, uses a new and readily prepared cinchona-derived bifunctional catalyst, is broad in scope, and tolerates a range of functionalities with high enantioselectivity (up to >99:1 e.r.). The significant scalability of this methodology was demonstrated with the synthesis of more than 80 grams of a pyrazoline product with 89 % catalyst recovery.
TL;DR: The racemic compound and both enantiomer were found to inhibit hMAO-A selectively and competitively and the selectivity of the enantiomers was explained by molecular modeling docking studies based on the PDB enzymatic models of MAO isoforms.
TL;DR: In this paper, Thiophene and furan-appended pyrazoline receptors R1 and R2 were designed and synthesized for selective detection of Al3+ ion.
TL;DR: These new pyrazolines would be promising potent inhibitors of drug sensitive and drug resistant Mycobacterium tuberculosis strain and potential anticancer agents against prostate cancer and other prototypes of cancers.
Abstract: Background Many synthetic procedures were reported till date to prepare pyrazoline derivatives. Some have published pyrazolines from different chalcone derivatives in the literature. Objective A series of new pyrazolines containing novel 2,5-dichloro-3-acetylthiophene chalcone moiety (PZT1-PZT20) have been synthesized, characterized by 1HNMR and 13CNMR and evaluated for them in vitro antitubercular activity against M. tuberculosis H37Rv strain and in vitro anticancer activity against DU-145 prostate cancer cell lines and all compounds were also screened for molecular docking studies against specific targeted protein domains. Methods All compounds were screened for potential activity against Mycobacterium tuberculosis H37Rv (MTB) strain and anticancer activity against DU-149 prostate cancer cell lines using MTT cytotoxicity assay. Results Among the series, compound PZT5 with 2", 4"-dichlorophenyl group at 5-position on the pyrazoline ring exhibited the most potent antitubercular activity (MIC=1.60 µg/mL) and compounds PZT2, PZT9, PZT11, PZT15, and PZT20 showed similar antitubercular activity against standard pyrazinamide (MIC=3.12 µg/mL) by broth dilution assay. PZT15 and PZT17 with 4"- pyridinyl and 2"-pyrrolyl groups on pyrazoline ring were found to exhibit better anticancer activity against DU-149 prostate cancer cell lines with IC50 values of 2.0±0.2 µg/mL and 6.0±0.3 µg/mL respectively by MTT assay. The preliminary structure-activity relationship has been summarized. The molecular docking studies with crystalline structures of enoyl acyl carrier protein reductase InhA interaction with target protein (2NSD; PDB and 3FNG; PDB) of Mycobacterium tuberculosis H37Rv (MTB) strain have also exhibited good ligand interaction and binding affinity. Ligand interaction and binding affinity were estimated using crystal structures of both types of enoyl acyl carrier protein reductase InhA (3FNG.pdb) and found to be much higher (-16.70 to - 19.20 kcal/mol) compared with pyrazinamide (-10.70 kcal/mol) as a standard target molecule. Whereas the binding affinities of six active compounds with crystal structure of other type of enoyl acyl carrier protein reductase InhA (2NSD.pdb) were much similar and higher (-9.30 to - 11.20 kcal/mole) than pyrazinamide (-11.10 kcal/mole). Conclusion These new pyrazolines would be promising potent inhibitors of drug sensitive and drug resistant Mycobacterium tuberculosis strain and potential anticancer agents against prostate cancer and other prototypes of cancers.
TL;DR: In this article, pyrazoline-thiazolidinones derived at fifth position with substituted arylidene groups were developed as potent inhibitors of Escherichia coli FabH (PDB: 5BNS) an antimicrobial target.
TL;DR: In this paper, four pyrazoline analogues were synthesized via intermolecular cyclization between substituted chalcones and hydrazine derivatives, and the toxicity analysis showed that compound 1 and 2 were toxic with LC 50 values of 11.47 and 0.97 μg/mL, respectively.
Abstract: Four pyrazoline analogues, 3-(4-methoxyphenyl)-5-naphthalene-1-yl-1-phenyl-4,5-dihydro-pyrazole (3) , 3-(4-methoxyphenyl)-5-naphthalene-1-yl-4,5-dihydro-1H-pyrazole (4) , 3-(2-methoxyphenyl)-5-naphthalene-1-yl-1-phenyl-4,5-dihydro-pyrazole (5) and 3-(2-methoxyphenyl)-5-naphthalene-1-yl-4,5-dihydro-1H-pyrazole (6) were synthesized via intermolecular cyclization between substituted chalcones and hydrazine derivatives. The compounds were synthesized in two steps. In the first step, the chalcones were synthesized by Claisen-Schmidt reaction. In the second step, they were cyclized with some hydrazine derivatives to form pyrazolines by using glacial acetic acid as a catalyst and assisted by microwave irradiation. The toxicity analysis showed that compound 1 and 2 were toxic with LC 50 values of 11.47 and 0.97 μg/mL, respectively. Furthermore, only compound 6 showed high antioxidant activity by using DPPH with an IC 50 value of 4.47 μg/mL.
TL;DR: In this paper, aryl trisubstituted pyrazoline that combines two chromophoric units in a non-conjugated manner is presented, and its crystal structure has been determined by single crystal X-ray crystallography.
TL;DR: In this paper, pyrene pyrazoline derivatives containing mono, di and tri methoxy phenyl substituents were synthesized and X-Ray Diffraction pattern revealed their crystalline nature.
Abstract: The pyrene pyrazoline derivatives containing mono, di and tri methoxy phenyl substituents were synthesized. Thermal stability and glass transition temperatures changed with progressive substitution of methoxy phenyl group. X-Ray Diffraction pattern revealed their crystalline nature. The photophysical properties of materials exhibited green emission at 510 nm (PP1My), 510 nm (PP2My) and 508 nm (PP3My) in solution and yellow emission at 580 nm (PP1My), 574 nm (PP2My) and 563 nm (PP3My) in solid state. The blue shift in the emission in solid state was owing to aggregation induced by methoxy substituent. The color chromaticity values were calculated for their color purity of green and yellow emissions. Ten different solvents were used to examine solvatochromism and red shifted emission observed in enhancing polarity of solvents and dual emission in cyclohexane were suggested twisted conformation of molecule that led to Intramolecular charge transfer becomes twisted Intramolecular charge transfer. Nonlinear optical properties of pyrazoline derivatives improved when electron donates methoxy groups and polyaromatic luminophore of pyrene were substituted on pyrazoline moiety. The third order nonlinear optical properties were investigated by Z-scan technique at 532 nm and exhibited strong reverse saturable absorption and self-defocusing natures. The optimized geometry evidences that molecules have twisted structures and looks like an antenna molecules. These kinds of molecules are demand in energy applications such as light harvesting solar materials and light emitting materials.
TL;DR: The study showed that CHC-SDS nanocapsules represent a promising nanocarrier for pyrazoline derivates that could be applied in leukemia therapy.
TL;DR: A novel series of chalcone bearing pyrazoline moieties synthesized and characterized by various analytical techniques showed the compounds P1, P2, P5, and P6 have produced the noteworthy inhibition on protein denaturation when compared to standard 98.17% whereas, the antiproteinase activity was in the range of 84.55- 90.44 %.
Abstract: A novel series of chalcone bearing pyrazoline moieties were (P1 to P7) synthesized and characterized by various analytical techniques. The anti-inflammatory studies showed the compounds P1, P2, P5, and P6 have produced the noteworthy inhibition on protein denaturation (81.39 - 96.57 %) when compared to standard 98.17% whereas, the antiproteinase activity was in the range of 84.55- 90.44 % when compared to the standard, 95.95 %. The compounds, P1, P2, P5 (2-Cl, 4- Cl & -NO2 substituent) bearing electron-withdrawing groups and the compounds P3 & P6 (4-N(CH3)2 & -OH substituent) possessing electron-donating group in its phenyl ring system exhibited the prominent activity. Further, to explore the molecular mechanism, the in-silico docking study against COX-2 enzyme was performed. The compounds were also screened for their antibacterial activities. Among them, the compounds P1, P2, P3, P5 and P6 showed the significant antibacterial activity against both gram-positive and gram-negative pathogen such as, Bacillus cereus, Staphylococcus aureus, Serratia marcescens and Staphylococcus typhi with maximum zone of inhibition within the range of 12-14 mm and 19-25 mm for 100 and 200 µg/ml concentrations respectively when compared to that of standard drug Gentamycin, whose ranges between 15-18 mm and 25-28 mm correspondingly.
24 Apr 2019
TL;DR: A series of polyaromatic luminophores based on pyrene pyrazoline containing donor-acceptor π-conjugation extended through naphthalene (PPN), anthracene (PPA) and pyrene (PPP) were designed and synthesized.
TL;DR: In this paper, the authors used FT-IR, 1H NMR, 13C NMR and analytical data to determine the three-dimensional structures of the compounds 4a and 4c.
TL;DR: In this article, a new analogue of fluorinated pyrazoline (compound 1) has been synthesized via one-pot three-component reaction in a sealed-vessel reactor, Monowave 50.
Abstract: A new analogue of fluorinated pyrazoline (compound 1) has been synthesized via one-pot three-component reaction in a sealed-vessel reactor, Monowave 50. The structure of compound 1 has been established by spectroscopy analysis, including UV, FT-IR, HRMS, 1H and 13C NMR spectroscopy. Based on the in silico studies, this compound showed a good potential as an inhibitor for dengue virus type 2 (DEN2) NS2B/NS3 serine protease and can be used as a reference in the next design of an antidengue virus.
DOI•
26 Feb 2019
TL;DR: A series of pyrazolines, oxazolines and pyrimidines bearing nabumetone moiety have been designed, synthesized, and evaluated as a potential cyclooxygenase-2 (COX-2) inhibitors and these results are compatible with their in vivo acute anti-inflammatory study for tested compounds.
Abstract: Department of Pharmacy, Baghdad College of Medical Science, Baghdad, Iraq. Department of Pharmacy, Ashur University College, Baghdad, Iraq. Department of Pharmaceutical Chemistry, College of Pharmacy, University of Mustansiriyah, Baghdad, Iraq. *Correspondence to Omar A. Yousif (email:omar.auday@yahoo.com). (Submitted: 07 October 2018 – Revised version received: 25 October 2018 – Accepted: 01 December 2018 – Published online: 26 February 2019)