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Molecules 2019, 24(2), 279;

Synthesis of Novel Pyrazole Derivatives and Their Tumor Cell Growth Inhibitory Activity

Institute of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China
Author to whom correspondence should be addressed.
Academic Editors: Carla Boga and Gabriele Micheletti
Received: 31 October 2018 / Revised: 6 January 2019 / Accepted: 10 January 2019 / Published: 13 January 2019
(This article belongs to the Special Issue Design and Synthesis of Organic Molecules as Antineoplastic Agents)
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To find novel antitumor agents, a series of 1H-benzofuro[3,2-c]pyrazole derivatives 4a-e were designed and synthesized. The treatment of 6-methoxybenzofuran-3(2H)-one 3 with LiHMDS in anhydrous tetrahydrofuran (THF) followed by reaction with 3-substitued phenyl isothiocyanate gave the thioamide intermediates, which underwent condensation with hydrazine monohydrate in dioxane/EtOH (1:1) to provide the benzofuropyrazole derivatives 4ae as well as the unexpected pyrazole derivatives 5ae. In tumor cell growth inhibitory assay, all the benzofuropyrazole derivatives were not active against the breast tumor MCF-7 cell, only 4a was highly active and more potent than ABT-751 against the leukemia K562 (GI50 = 0.26 μM) and lung tumor A549 cells (GI50 = 0.19 μM), while other benzofuropyrazoles showed very weak inhibitory activity. In contrast, the pyrazoles 5a-e were in general more potent than the benzofuropyrazoles 4ae. Compound 5a exhibited a similar tendency to that of 4a with high potency against K562 and A549 cells but weak effects on MCF-7 cell. Both pyrazoles 5b and 5e exhibited high inhibitory activities against K562, MCF-7 and A549 cells. The most active compound 5b was much more potent than ABT-751 against K562 and A549 cells with GI50 values of 0.021 and 0.69 μM, respectively. Moreover, 5b was identified as a novel tubulin polymerization inhibitor with an IC50 of 7.30 μM. View Full-Text
Keywords: privileged structure; pyrazoles; tubulin inhibitors; antitumor; antitumor agents privileged structure; pyrazoles; tubulin inhibitors; antitumor; antitumor agents

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Cui, Y.-J.; Tang, L.-Q.; Zhang, C.-M.; Liu, Z.-P. Synthesis of Novel Pyrazole Derivatives and Their Tumor Cell Growth Inhibitory Activity. Molecules 2019, 24, 279.

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