A NEW HETEROCYCLIC COMPOUND: CRYSTAL STRUCTURE AND ANTICANCER ACTIVITY AGAINST HUMAN LUNG ADENOCARCINOMA CELLS
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A NEW HETEROCYCLIC COMPOUND: CRYSTAL STRUCTURE AND ANTICANCER ACTIVITY AGAINST HUMAN LUNG ADENOCARCINOMA CELLS E.-H. Shi1, L.-R. Wang1, S. Zhao1, L. Shen1, C.-Y. Zhang1, X.-X. Li1, H. Li2, and D.-L. Zhang1*
New heterocyclic compound (S)-3-(4-(5-bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran (1), designed by utilizing 5-bromo-2-chlorobenzoic acid (2) as the starting material, is obtained by the organic synthesis and then characterized by single crystal X-ray crystallography, 1H NMR and IR spectroscopy. In the biological study, the CCK-8 assay is performed to evaluate the inhibitory effect of the compound on SPC-A-1 human lung adenocarcinoma cells in vitro by measuring the cancer cell viability. Then, the anticancer activity of the compound is also confirmed by the in vivo xenograft experiment by measuring the mice body weight and the cancer volume. DOI: 10.1134/S0022476620070215 Keywords: heterocycles, X-ray, anticancer, molecular docking, lung adenocarcinoma.
INTRODUCTION One of the leading causes of death worldwide is cancer [1-3]. The World Bank income groups stated that from 2008 to 2030, 12.7 million cancer case incidences will increase to 21.4 million [4, 5]. In spite of enormous efforts to generate available chemotherapy drugs, significant toxicity and selectivity problems remain. The resistance of cancer cells to anticancer agents and the modern chemotherapy toxicity stimulates us to look for novel therapies and prevention approaches of the potential disease [6]. Empagliflozin is a medicinally crucial ary1 glycoside used in the therapy of type 2 diabetes [7]. In the synthesis of empagliflozin, (S)-3-(4-(5-bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran (1) is one of the most crucial intermediates [8, 9]. Hence, substantial attention has been paid to the synthesis, crystal configuration and characterization of compound 1, which have not been reported previously. This work describes the characterization and synthesis of title compound 1. Compound 1 was designed by the use of 5-bromo-2-chlorobenzoic acid (2) as the starting material yielding (5-bromo-2-chlorophenyl)(4-fluorophenyl) methanone (3). It reacted with (S)-tetrahydrofuran-3-ol to produce (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (4). We obtained title compound 1 after the reduction of compound 4 with 1,1,3,3-tetramethyldisiloxane (Scheme 1). Furthermore, the inhibitory effect and cytotoxicity of the compound on SPC-A-1 human lung adenocarcinoma cells were
1
Medical Oncology, Heilongjiang Province Hospital, Harbin, Heilongjiang, P. R. China; *[email protected]. Department of Orthopedics, Zhejiang University, Yiwu, Zhejiang, P. R. China. Original article submitted August 12, 2019; revised October 22, 2019; accepted November 22, 2019.
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0022-4766/20/6107-1167 © 2020 by Pleiades Publishing, Ltd.
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evaluated by the CCK-8 assay. The results indicated the excellent antitumor activity of the compound in vitro by reducing the cancer cell viability. Then, in vivo xenograft experiments were conducted to explore the effe
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