Solvent and Copper Ion-Induced Synthesis of Pyridyl–Pyrazole-3-One Derivatives: Crystal Structure, Cytotoxicity
Qiu Ping Huang,
Shao Nan Zhang,
Shu Hua Zhang,
Kai Wang,
Yu Xiao
Affiliations
Qiu Ping Huang
Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Collaborative Innovation Center for Exploration of Hidden Nonferrous Metal Deposits and Development of New Materials in Guangxi (College of Chemistry and Bioengineering), Guilin University of Technology, Guilin 541004, China
Shao Nan Zhang
Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Collaborative Innovation Center for Exploration of Hidden Nonferrous Metal Deposits and Development of New Materials in Guangxi (College of Chemistry and Bioengineering), Guilin University of Technology, Guilin 541004, China
Shu Hua Zhang
Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Collaborative Innovation Center for Exploration of Hidden Nonferrous Metal Deposits and Development of New Materials in Guangxi (College of Chemistry and Bioengineering), Guilin University of Technology, Guilin 541004, China
Kai Wang
Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Collaborative Innovation Center for Exploration of Hidden Nonferrous Metal Deposits and Development of New Materials in Guangxi (College of Chemistry and Bioengineering), Guilin University of Technology, Guilin 541004, China
Yu Xiao
Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, Collaborative Innovation Center for Exploration of Hidden Nonferrous Metal Deposits and Development of New Materials in Guangxi (College of Chemistry and Bioengineering), Guilin University of Technology, Guilin 541004, China
Five novel compounds, methyl 5-(acetyloxy)-1-(6-bromo-2-pyridinyl)-1H-pyrazole-3-carboxylate (1), methyl 1-(6-bromo-2-pyridinyl)-5-hydroxy-1H-pyrazole-3-carboxylate (2), Trimethyl 1,1′,1′′-tris(6-bromo-2-pyridinyl)-5,5′′-dihydroxy-5′-oxo-1′,5′-dihydro-1H,1′′H-4,4′: 4′,4′′-terpyrazole-3,3′,3′′-tricarboxylate (H2L1, 3), [Cu2(L2)2]·CH3OH (4), H2L2A·CH3CN (5) were synthesized. Compounds 1–5 characterized by elemental analysis, IR, and X-ray single-crystal diffraction. And 1–3 were also characterized by 1H NMR, 13C NMR and ESI-MS. The H2L1, H2L2 were formed by in-situ reaction. H2L2 and H2L2A are mesomer compounds which have two chiral carbons. The antitumor activity of compounds 1–5 against BEL-7404, HepG2, NCI-H460, T-24, A549 tumor cell lines were screened by methylthiazolyl tetrozolium (MTT) assay. The compounds 1, 2 showed weakly growth inhibition on the HepG2 cell lines. The HepG2 and A549 cell lines showed higher sensitivity to compound 4, while the IC50 values are 10.66, 28.09 μM, respectively. It is worth noting that compounds 1–5 did not show cytotoxicity to human normal liver cell line HL-7702, suggesting its cytotoxic selectivity on these tumor cell lines.
