Homologous 1,3,5-triarylpyrazolines: synthesis, CHÁ Á Áp interactions guided self-assembly and effect of alkyloxy chain length on DNA binding properties (original) (raw)
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RSC Advances
We have designed and synthesized three pyrazole analogs (4, 5a, 5b), pyrazole-based chalcones (6a–6d) and (8a–8h), and N-formyl/acetyl 1,3,5-trisubstituted pyrazole analogs (7a–7d), (9a–9d) via Suzuki cross-coupling as the key step.
Journal of Chemistry, 2012
A number of 3-[4-(benzyloxy)-3-(2-Chlorophenylazo)-phenyl]-5-(substituted-phenyl)-1-substituted-2-pyrazolines(4a-j) and (5a-j) have been synthesized by diazotization of 2-chloroaniline and its coupling reaction with 4-hydroxy acetophenone, followed by benzyloxation of the hydroxyl group to give the substrate [4-benzyloxy-3-(2-chlorophenylazo)acetophenone (1)].The prepared starting material (1) has been reacted with different substituted benzaldehydes to give a new series of chalcone derivatives 1-[(4-benzyloxy)-3-(2-chloro-phenylazo)-phenyl]-3-(substituted phenyl)-2-propen-1-one (3a-j) , in high yields and in a few minutes, and the later compounds were treated with hydrazine hydrate according to Michael addition reaction to afford a new biolological active target compounds (4a-j) and (5a-j). Furthermore, The structures of the newly synthesized compounds were confirmed by FT-IR, 13 C-NMR, 13 C-DEPT & 1 H-NMR spectral data. The chalcone and pyrazoline derivatives were evaluated for their anti bacterial activity against Escherichia coli as gram negative and Staphylococcus aureus as gram positive, the results showed significant activity against both types of bacteria.
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014
h i g h l i g h t s Pyrazolines are attractive drug scaffold with many biological applications. Synthesis of new pyrazoline derivatives equipped with N-acyl arms and long alkoxy side chains. Spectral, self-assembly, antifungal and anti-inflammatory studies. Effect of alkoxy chain length on molecular packing and bioactivity. g r a p h i c a l a b s t r a c t A series of new pyrazoline derivatives equipped with N-acyl arms and long alkoxy groups as side chains was synthesized to investigate the effect of alkoxy chain length on molecular packing and bioactivity. 1b 1c A b-4b c-4c
Journal of Applied Pharmaceutical Science
The development of resistance and side effects of chemotherapeutic drugs are common obstacles in the treatment of cancer. With the expansion of health problems nowadays, there is a need to continuously develop new drugs that are more efficient in targeting tumor cells and safe to normal cells. This study designed a series of new chalcones and pyrazoline derivatives based on their binding energy from the molecular docking study. The synthesis involved Claisen-Schmidt condensation to form two chalcones, 1 and 2, which are then cyclized at room temperature to form eight new pyrazoline derivatives, 3-10. A one-pot reaction of acetophenone, 2-ethoxybenzaldehyde, and hydrazide derivatives (thiosemicarbazide and phenyl hydrazide) under reflux formed two new pyrazoline derivatives, 11 and 12, without the isolation of chalcones. All the synthesized chalcones and pyrazolines were characterized using the Fourier transform infrared spectroscopy-attenuated total reflectance and nuclear magnetic resonance (1D and 2D). The cytotoxicity activity of the chalcones and new pyrazoline compounds were investigated against breast cancer cell lines (MCF-7 and MD-MB-231) and normal breast cell lines (MCF-10A). The results show that only compound 7 showed the minimum inhibition against MCF-7 with IC 50 6.50 µM when exposed to the cell line for 24 hours compared to the reference Gefitinib anticancer drug.
Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents
Molecules, 2015
New pyrazoline derivatives were synthesized and evaluated for their cytotoxic effects on AsPC-1 human pancreatic adenocarcinoma, U87 and U251 human glioblastoma cell lines. 1-[((5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetyl]-3-(2-thienyl)-5-(4-chlorophenyl)-2-pyrazoline (11) was found to be the most effective anticancer agent against AsPC-1 and U251 cell lines, with IC50 values of 16.8 µM and 11.9 µM, respectively. Tumor selectivity of compound 11 was clearly seen between Jurkat human leukemic T-cell line and human peripheral blood mononuclear cells (PBMC). Due to its promising anticancer activity, compound 11 was chosen for apoptosis/necrosis evaluation and DNA-cleavage analysis in U251 cells. Compound 11-treated U251 cells exhibited apoptotic phenotype at low concentration (1.5 µM). DNA-cleaving efficiency of this ligand was more significant than cisplatin and was clearly enhanced by Fe(II)-H2O2-ascorbic acid systems. This result pointed out the relationship between the DNA cleavage and the cell death.
International Journal of Molecular Sciences
Herein we describe a combined experimental and in silico study of the interaction of a series of pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-one derivatives (PBTs) with parallel G-quadruplex (GQ) DNA aimed at correlating their previously reported anticancer activities and the stabilizing effects observed by us on c-myc oncogene promoter GQ structure. Circular dichroism (CD) melting experiments were performed to characterize the effect of the studied PBTs on the GQ thermal stability. CD measurements indicate that two out of the eight compounds under investigation induced a slight stabilizing effect (2–4 °C) on GQ depending on the nature and position of the substituents. Molecular docking results allowed us to verify the modes of interaction of the ligands with the GQ and estimate the binding affinities. The highest binding affinity was observed for ligands with the experimental melting temperatures (Tms). However, both stabilizing and destabilizing ligands showed similar scores, whilst M...
Acta Poloniae Pharmaceutica, 2023
In this study, a series of novel 2-pyrazoline derivatives were synthesized and their structures were established by using spectral methods. The antiproliferative activities of compounds were investigated against human cell lines A-549 and MCF-7 by MTT assay and L-929 (mouse normal fibroblast) cell cytotoxicity was also examined. Apoptotic effects of the compounds in breast and lung cancer cells were assessed by Annexin V-FITC apoptosis assay using flow cytometry. The antiproliferative effect on lung carcinoma of the synthesized compounds was higher than breast carcinoma. Moreover, it was observed that none of the synthesized compounds have cytotoxic activity in healthy cells. Flow cytometry studies have shown that compounds induced apoptosis at high concentrations. Additionally, fluorescence cell imaging studies were performed for the first time in A-549 and MCF-7 cancer cell lines to determine the potential of the biosensor compounds by fluorescence microscopy. Compounds 4b, 4d, 4e, and 4f showed fluorescence properties by considering microscopic imaging.
Journal of Molecular Structure, 2006
1,5-diaminotetrazole at conditions of its interaction with chalcones (1,3-diphenylpropenones) in hot DMF undergoes Dimroth rearrangement to 5-tetrazolylhydrazine, which results in formation of 1-(5-tetrazolyl)-3,5-diaryl-D 2-pyrazolines (I). Structure of the obtained products was confirmed by their parallel synthesis and X-ray structural analysis. Unusual fluorescence behavior of the tetrazolopyrazolynes in polar solvents was attributed to the dissociation of their highly acidic tetrazole N-H group. The last hypothesis was confirmed at the investigation of the protolytic interactions of I with tertiary amine.