Synthesis and in-vitro antioxidant and antitumor evaluation of novel pyrazole-based heterocycles

Abstract

Hydrazide-hydrazone, namely, N′-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)-2-cyanoacetohydrazide 3, was utilized as a key starting material for the construction of a variety of novel heterocyclic moieties. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 1 H-NMR, and mass spectra). Some of the newly synthesized compounds were screened for their antitumor and antioxidant activities. The results showed clearly that compounds 6, 11, 13, 22, and 29 displayed promising in-vitro antitumor activity against two cell lines (HepG2 and MCF-7). Among these compounds, compounds 13 and 29 exhibited the highest activity as antitumor agents. On the other hand, compounds 13, 22, and 29 exhibited the highest inhibitory antioxidant activity using ABTS method. While, in case of erythrocytes hemolysis, compounds 4, 13, and 29 proved to exhibit potent antioxidative activity as vitamin C. Meanwhile, compounds 6, 11, 16, 21, and 22 showed a remarkable promising activity. In light of the highest potency of our novel compounds in targeting both antitumor and antioxidant activities, compounds 13 and 29 warrant persistent preclinical development as antitumor and antioxidant agents.

Cytotoxic Effects of Newly Synthesized Heterocyclic Candidates Containing Nicotinonitrile and Pyrazole Moieties on Hepatocellular and Cervical Carcinomas

“…The nicotinonitriles were obtained by two different ways, from the reaction of chalcone with ethylcyanoacetate, ammonium acetate and drops of piperidine as a base and from one pot four components reaction of methylketone, aldehyde, ethylcyanoacetate, ammonium acetate and drops of piperidine as a base [15]. In prolongation of our work in the synthesis of heterocyclic compounds and evaluation of their medicinal importance [16,17,18,19,20,21,22,23,24,25,26,27] and based on the literature survey about the pharmacological and medicinal importance of pyrazoles and nicotinonitriles, we have devoted our efforts to design and synthesize novel heterocyclic compounds containing pyrazol and nicotine-nitrile moieties, 4-(3-(4-fluorophenyl)-1-phenyl-1 H -pyrazol-4-yl)-2-hydroxy-6-(naphthalen-1-yl)-nicotinenitrile 8 has been obtained by reacting of 1-acetylnaphthalene ( A ), 3-(4-fluorophenyl)-1-phenyl-1 H -pyrazole-4-carbaldehyde ( B ), ethyl 2-cyanoacetate, ammonium acetate and piperidine (Scheme 1).…”

Synthesis, Antiproliferative, and Antioxidant Evaluation of 2-Pentylquinazolin-4(3H)-one(thione) Derivatives with DFT Study

“…The reference anticancer drug used was Doxorubicin. The MTT assay was carried out at the pharmacology department, Faculty of pharmacy, Mansoura University, Egypt according to the reported literatures [42,43,54]. The cells were cultured in a RPMI-1640 medium with 10% fetal bovine serum, followed by the addition of antibiotics (100 units/mL penicillin and 100 µg/mL streptomycin) at 37 °C in a 5% CO 2 incubator.…”

Mono-Alkylated Ligands Based on Pyrazole and Triazole Derivatives Tested Against Fusarium oxysporum f. sp. albedinis: Synthesis, Characterization, DFT, and Phytase Binding Site Identification Using Blind Docking/Virtual Screening for Potent Fophy Inhibitors

“…One of the important five-membered hetero atomic rings, where nitrogen and sulfur are separated by one carbon, is 1,3-thiazole, prepared by original strategies. It is a pharmacophore, a privileged scaffold, in many compounds with several biological activities (Reis et al, 2011;Fadda et al, 2012;Alegaon et al, 2014;Bekhit et al, 2015;Varghese et al, 2016;El-Naggar and Abdel-Mottaleb, 2017;El-Sayed and Ismail, 2019;Nayak and Gaonkar, 2019;Pricopie et al, 2019). Pyrazole is a five-membered heterocyclic with two adjacent nitrogen atoms, common in a variety of commercial compounds applied in many industrial fields (Pongor et al, 2004;Elayyachy et al, 2005;Bouabdallah et al, 2006;Dawood and Abdel-Wahab, 2012;Abrigach et al, 2014;Singh et al, 2014Singh et al, , 2016Akhtar et al, 2017).…”