Mono- and binuclear
Cu(II) complexes bearing an unsymmetrical bipyridine–pyrazole–amine
ligand were synthesized and characterized using X-ray diffraction.
The mononuclear complex could be converted to the corresponding binuclear
complexes under basic conditions due to the lability of the pyrazolyl
N–
H
. Both complexes proved to
be effective catalysts for azide–alkyne cycloaddition to form
triazoles, with the binuclear complex exhibiting higher catalytic
activity than the corresponding mononuclear one. The binuclear complex
was effective at catalyst loadings as low as 0.0125 mol %, making
it one of the most active catalysts for this reaction to date. Therefore,
this catalyst was applied in the synthesis of potentially biologically
active molecules. At 0.1–0.3 mol % catalyst loading, three
precursors of Sorafenib analogs were synthesized in excellent yields.
A one-pot variant of the reaction, generating the azide in
situ, could also be performed using the binuclear complex
as the catalyst. The transition metal complex bearing an unsymmetrical
ligand may exhibit excellent catalytic activity, which represents
a direction for developing new highly active catalysts.
The development of cancer treatments requires continuous exploration and improvement, in which the discovery of new drugs for the treatment of cancer is still an important pathway. In this study, based on the molecular hybridization strategy, a new structural framework with an N-aryl-N’-arylmethylurea scaffold was designed, and 16 new target compounds were synthesized and evaluated for their antiproliferative activities against four different cancer cell lines A549, MCF7, HCT116, PC3, and human liver normal cell line HL7702. The results have shown seven compounds with 1-methylpiperidin-4-yl groups having excellent activities against all four cancer cell lines, and they exhibited scarcely any activities against HL7702. Among them, compound 9b and 9d showed greatly excellent activity against the four kinds of cells, and the IC50 for MCF7 and PC3 cell lines were even less than 3μM.
Based on the results of the biological activity test, the target compounds have exhibited the β-catenin translocation capability and the ALP activation activity.
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