New synthesis of two tridentate bipyrazolic compounds and their cytotoxic activity tumor cell lines

Abstract

Two new tripodal compounds - 4-{bis[(3,5-dimethyl-1H-pyrazole-1-yl)methyl]amino}butane-1-ol (1); ethyl 1-[((2-hydroxyethyl){[3-(ethoxycarbonyl)-5-methyl-1H-pyrazole-1-yl]methyl} amino)methyl]-5-methyl-1H-pyrazole-3-carboxylate (2) were reported. The evaluation of the cytotoxic properties in vitro of these ligands, was examined on two tumor cell lines - P815 (mastocytome murine) and Hep (carcinoma of human larynx). The concentration required to induce 50% of lysis (IC(50)) was more pronounced against P815 cell line (IC(50): 39.42 microg mL(-1) for the compound 1 and 97.74 microg mL(-1) for the compound 2) than the Hep cell line (IC(50): 83.49 microg mL(-1) for compound 1 and 185.30 microg mL(-1) for compound 2). Statistical analysis shows that the compound 1 is two to three folds more cytotoxic than the compound 2 (p < 0.05). Interestingly, the cytotoxic activity depends strongly on both the substituents linked to the aminic nitrogen and pyrazolic rings.

Synthesis, Characterization, Antimicrobial Activity, and Docking Studies of New Triazolic Tripodal Ligands

“…Then, the mixture was stirred at 65°C during 6 h. After filtration and evaporation to dryness, the obtained residue was purified through silica column using diethyl ether/ methanol 95:5 to give 6 as yellow oil (1.08 g, 67%). IR (7). To a mixture of 4 (1.5 g, 11.4 mmol) and anhydrous sodium carbonate (3.02 g, 28.5 mmol) in acetonitrile (30 ml), was added isopropane (0.34 g, 5.7 mmol) in acetonitrile (20 ml).…”

“…In our laboratory, a number of pyrazole based tripodal ligands have been studied . These ligands incorporating in their structures two sp 2 and sp 3 hybridized amine nitrogen atoms, could be distinguish according to their side arms and the nature of junctions (N–C–N or N–C–C) that bound the pyrazole ring to the lateral arm.…”

“…These ligands incorporating in their structures two sp 2 and sp 3 hybridized amine nitrogen atoms, could be distinguish according to their side arms and the nature of junctions (N–C–N or N–C–C) that bound the pyrazole ring to the lateral arm. Therefore, they were found in several fields such as catalysis, extraction of heavy metals and pharmacology . However, some studies have reported that such ligands present no antibacterial activities similarly to the thiophene tripods .…”

“…Therefore, they were found in several fields such as catalysis, [7] extraction of heavy metals [9] [10] and pharmacology. [7][8] [11] However, some studies have reported that such ligands present no antibacterial activities [12] similarly to the thiophene tripods. [13] Thus, it will be worth attempting to substitute the pyrazole or the thiophene by the 1,2,4-triazole ring, in the aim to generate a new family of trident structures with different lateral arms.…”

Synthesis of pyrazole derivatives and their spectroscopic properties investigated using both experimental and theoretical approaches

“…It has also been reported that the bridging carbon atom can be modified by the organic functional groups to form novel heteroscorpionate ligands 12 that are tailored toward different research applications like anticancer agents. [13][14][15] The coordination behaviour of these types of compounds can be easily adjusted by changing the electronic and steric characteristics of substituents on the 3-, 4-or 5-positions of the pyrazole ring. 12 Several pyrazole derivatives and their metal complexes have been reported in the literature [16][17][18][19] but very little attention has been paid to the atomic properties of the nitrogen donor atoms and their availability for metal coordination.…”