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Molecules 2017, 22(11), 1813; doi:10.3390/molecules22111813

Solvent and Copper Ion-Induced Synthesis of Pyridyl–Pyrazole-3-One Derivatives: Crystal Structure, Cytotoxicity

1
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
2
College of Chemistry and Engineering, Guangxi Normal University for Nationalities, Chongzuo 532200, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 12 September 2017 / Revised: 19 October 2017 / Accepted: 24 October 2017 / Published: 25 October 2017
(This article belongs to the Special Issue Pyrazole Derivatives)
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Abstract

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 15 characterized by elemental analysis, IR, and X-ray single-crystal diffraction. And 13 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 15 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 15 did not show cytotoxicity to human normal liver cell line HL-7702, suggesting its cytotoxic selectivity on these tumor cell lines. View Full-Text
Keywords: pyridyl–pyrazole-3-one derivatives; crystal structure; antitumor activity; in-situ reaction pyridyl–pyrazole-3-one derivatives; crystal structure; antitumor activity; in-situ reaction
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MDPI and ACS Style

Huang, Q.P.; Zhang, S.N.; Zhang, S.H.; Wang, K.; Xiao, Y. Solvent and Copper Ion-Induced Synthesis of Pyridyl–Pyrazole-3-One Derivatives: Crystal Structure, Cytotoxicity. Molecules 2017, 22, 1813.

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