Synthesis of New Thiazolyl-Pyrazoline Derivatives and Evaluation of Their Antimicrobial, Cytotoxic and Genotoxic Effects

Sever, Belgin; Altıntop, Mehlika Dilek; Gençer, Hülya Karaca; Kapkac, Handan Acelya; Atlı, Özlem; Baysal, Merve; Özdemır, Ahmet

doi:10.2174/1570180814666170925152902

Cited by 9 publications

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“…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%

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

et al. 2018

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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

et al. 2018

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“…[4][5][6] Heterocyclic rings are commonly used in the drug design of biologically active substances. [7][8][9] Recently thiazole-based derivatives were proposed as potential lead compounds for the development of novel cholinesterase inhibitors or receptors for advanced glycation end-products (RAGE) antagonists. [10][11][12] It was reported that the thiazole ring was able to create crucial interactions with the amino acid residues at the level of the active site of AChE.…”

Section: Introductionmentioning

confidence: 99%