Synthesis of 1-acetyl-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and evaluation of their anticancer activity

Özdemir, Ahmet; Altıntop, Mehlika Dilek; Kaplancıklı, Zafer Asım; Turan-Zitouni, Gülhan; Çiftçi, Gülşen Akalın; Yıldırım, Şafak Ulusoylar

doi:10.3109/14756366.2012.724682

Cited by 17 publications

(9 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Prompted by the aforementioned findings and in the continuation of our ongoing research in the field of design, synthesis, and biological evaluation of pyrazoline derivatives [30][31][32][33][34][35], herein we described the synthesis and evaluation of a new series of heteroaryl substituted pyrazolines as potential anticancer agents against AsPC-1 human pancreatic adenocarcinoma and two glioblastoma cell lines, U87 and U251 cell lines. Furthermore, tumor selectivity test on blood cells (PBMC and Jurkat cells) and the apoptotic, necrotic, and DNA-cleavage analysis against U251 cells were carried out using the most effective compound.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

et al. 2015

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

et al. 2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…The synthesis of new pyrazoline derivatives ( 3a – i , 4a – i ) followed the general pathway depicted in Scheme 1 . Initially, 1,3-diaryl-substituted chalcones ( 1 , 2 ) were synthesized via the base-catalyzed Claisen–Schmidt condensation of 2-acetylfuran/2-acetylthiophene with the appropriate aromatic aldehydes [ 29 , 30 , 31 , 32 ]. Then, the final compounds, 1-(phenyl/4-substituted phenyl)-3-(2-furanyl/thienyl)-5-aryl-2-pyrazolines ( 3a – i , 4a – i ), were obtained via the cyclization of the chalcones ( 1 , 2 ) with suitable phenylhydrazine hydrochloride derivatives in the presence of hot acetic acid [ 33 ].…”

Section: Resultsmentioning

confidence: 99%

“…2-Acetylfuran/2-acetylthiophene (0.02 mol), proper aromatic aldehyde (0.02 mol) and 40% ( w / v ) sodium hydroxide (5 mL) in ethanol (30 mL) were stirred at room temperature for 24 h. Then, the reaction mixture was poured into ice and the precipitated solid was filtered, washed with water, and dried. The product was crystallized from ethanol [ 29 , 30 , 31 , 32 , 33 , 34 ].…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Neuroprotective Effects of a Series of Pyrazolines against 6-Hydroxydopamine-Induced Oxidative Stress

et al. 2018

Self Cite

View full text Add to dashboard Cite

Parkinson’s disease (PD) is a chronic, progressive, and age-related neurodegenerative disorder characterized by the loss of midbrain dopaminergic neurons caused by the accumulation of free radicals and oxidative stress. Based on the neuroprotective properties of 2-pyrazoline derivatives, in the current work, 1-(phenyl/4-substituted phenyl)-3-(2-furanyl/thienyl)-5-aryl-2-pyrazolines (3a–i, 4a–i) were synthesized via the cyclization of the chalcones (1, 2) with suitable phenylhydrazine hydrochloride derivatives. All these compounds were investigated for their neuroprotective effects using an in vitro 6-hydroxydopamine (6-OHDA)-induced neurotoxicity model of PD in the rat pheochromocytoma (PC-12) Adh cell line. In addition, some different pharmacokinetic parameters of all compounds were in silico predicted by the QikProp module of Schrödinger’s Maestro molecular modeling package. 4-Methylsulfonylphenyl substituted compounds 3h (20%) and 4h (23%) were determined as the most promising neuroprotective agents related to their inductive roles in cell viability when compared with the 6-OHDA-positive control group (43% and 42%, respectively). Moreover, in silico pharmacokinetic results indicated that all compounds were within the acceptable range intended for human use. According to both in vitro and in silico studies, compounds 3h and 4h draw attention as potential orally bioavailable therapeutic drug candidates against neurodegeneration in PD.

show abstract

“…Cell culture and drug treatment NIH/3T3 mouse embriyonic fibroblast cells (ATCC ® CRL-1658™) were cultured and drug treatments were performed as reported previously. 29…”

Section: Determination Of Cox Inhibitory Activitymentioning

confidence: 99%

Microwave-assisted synthesis of a series of 4,5-dihydro-1H-pyrazoles endowed with selective COX-1 inhibitory potency

Altıntop

Temel

Özdemir

2023

JSCS

View full text Add to dashboard Cite

More efforts have been directed towards the discovery of selective COX-1 inhibitors due to recent works highlighting the involvement of COX-1 in the pathogenesis of pain, neuroinflammation, cancer and cardiovascular disorders. In this context, this paper aims to describe 2-pyrazolines endowed with selective COX-1 inhibitory potency. An efficient microwave-assisted protocol was applied for the preparation of a series of pyrazolines, which were tested for their COX-1 and COX-2 inhibitory effects using a colorimetric assay. The cytotoxic properties of the most potent derivatives on NIH/3T3 fibroblast cells were determined using MTT method. 1-(3-Fluorophenyl)-5-(3,4-methylen-dioxyphenyl)-3-(2-thienyl)-4,5-dihydro-1H-pyrazole (2g) and 1-(3-bromophe-nyl)-5-(3,4-methylendioxyphenyl)-3-(2-thienyl)-4,5-dihydro-1H-pyrazole (2h) were determined as selective COX-1 inhibitors. According to the in silico data obtained from Schr?dinger's QikProp module, both compounds are estimated to possess favorable oral bioavailability and drug-likeness. This work could be a rational guideline for further modifications at different sites on 2-pyrazoline motif to bring out a new class of selective COX-1 inhibitors.

show abstract

Synthesis of 1-acetyl-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and evaluation of their anticancer activity

Abstract: (2013) Synthesis of 1-acetyl-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and evaluation of their anticancer activity,

Cited by 17 publications

References 28 publications

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

Design, Synthesis, and Neuroprotective Effects of a Series of Pyrazolines against 6-Hydroxydopamine-Induced Oxidative Stress

Microwave-assisted synthesis of a series of 4,5-dihydro-1H-pyrazoles endowed with selective COX-1 inhibitory potency

Contact Info

Product

Resources

About