Synthesis and Antiproliferative Activity of Novel Indazole-Chalcone Hybrids

doi:10.11944/j.issn.1000-0518.2019.09.190045

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (9): 1015-1022.DOI: 10.11944/j.issn.1000-0518.2019.09.190045

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Synthesis and Antiproliferative Activity of Novel Indazole-Chalcone Hybrids

GONG Yilin,SHI Jiantao,WANG Yang,CHEN Ye,DING Shi(),LIU Yang,LIU Ju()

Key Laboratory of New Drug Research and Development of Liaoning Province,College of Pharmacy,Liaoning University,Shenyang 110036,China

Received:2019-02-21 Accepted:2019-05-17 Published:2019-09-05 Online:2019-09-05
Contact: Ju LIU
Supported by:
Supported by the Shenyang Science & Technology Project(No.18-013-0-03), the Youth National Natural Science Foundation of China(No.21807055)

Abstract

Abstract:

Nine novel indazole-chalcone hybrids(4a-4i) have been synthesized by condensation of substituted 4-(3-oxo-3-phenylprop-1-en-1-yl) benzoic acid with 4-morpholino-1H-indazol-3-amine prepared from 2,6-difluorobenzonitrile by amination with morpholine and then cyclisation with hydrazine hydrate. Their chemical structures were confirmed by Fourier transform infrared spectrometer(FTIR), nuclear magnetic resonance spectroscopy(NMR), mass spectrometry(MS) and elemental analysis. Compounds(4a-4i) were screened for in vitro antiproliferative activities against human gastric cancer cell line(MKN45) and human lung adenocarcinoma cell line(A549). Most of the designed compounds were found to exhibit potential antiproliferative activities. Among them, compounds 4a and 4d exhibited remarkable inhibitory activity against MKN45 cell lines with IC₅₀ value of 2.65 and 3.55 μmol/L, respectively, which were more potent than that of the positive control sorafenib(IC₅₀=4.69 μmol/L).

Key words: indazole, chalcone, antiproliferative activity

GONG Yilin, SHI Jiantao, WANG Yang, CHEN Ye, DING Shi, LIU Yang, LIU Ju. Synthesis and Antiproliferative Activity of Novel Indazole-Chalcone Hybrids[J]. Chinese Journal of Applied Chemistry, 2019, 36(9): 1015-1022.

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Synthesis and Antiproliferative Activity of Novel Indazole-Chalcone Hybrids

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