Abstract
Purpose: To carry out a neat synthesis of 2-amino-5,6-dihydro-8-methoxy-4-phenylbenzo[h]quinoline-3- carbonitrile (compound 2) and 2-amino-5,6-dihydro-8-methoxy-4-phenyl-4H-benzo[h]chromene-3- carbonitrile (compound 3) and evaluate their cytotoxic activity in human glioblastoma cells.Methods: Benzo[h]quinoline and benzo[h]chromene were synthesized by treating 6-methoxy-1- tetralone with benzylidenemalononitrile under microwave irradiation. The structures of compounds 2 and 3 were confirmed by elemental, spectral, and x-ray crystallographic analyses. The cytotoxic activity of compounds 2 and 3 was evaluated using WST-1 assay in U373 human glioblastoma cell line.Results: The molecular structures of compounds 2 and 3 were demonstrated unambiguously from single crystal x-ray measurements and they crystallized in triclinic form, P-1, for both compounds. In vitro cytotoxic activity data for compound 2 in human glioblastoma cell line (U373) indicate that no significant cytotoxicity was observed. On the other hand, compound 3 showed highly significant cytotoxic effects on U373 cells at concentrations starting from 0.1 μg/ mL.Conclusion: Compound 3 produces a decrease in cell viability with approximately 80 % cell death while compound 2 did not indicate significant cytotoxic activity. This suggests that the chromene moiety of compound 3 may be responsible for its high cytotoxicity.Keywords: Hydronaphthaline, Benzo[h]quinolone, Benzo[h]chromene, X-ray crystallography, U373 human glioblastoma, Cytotoxicity, Chromene moiety
Highlights
Literature survey has demonstrated the diversity of pharmacological applications of fused chromenes such as, anticancer [1,2], antibacterial [3], anti-inflammatory [4], antioxidants [5,6] and antiprotozoal [7] activities
Based on the above knowledge and in continuation of our previous work [17,18,19], the present study provides an evidence for the high efficient biological activity of the synthesized benzo[h]quinoline and benzo[h]chromene derivatives as anticancer compounds
The structures of benzo[h] quinoline-3carbonitrile 2 and benzo[h]chromene-3carbonitrile 3 have been established by x-ray crystallography and supported by spectral data
Summary
Literature survey has demonstrated the diversity of pharmacological applications of fused chromenes such as, anticancer [1,2], antibacterial [3], anti-inflammatory [4], antioxidants [5,6] and antiprotozoal [7] activities. Fused quinoline derivatives produce wide pharmacological activities such as antibacterial [8,9], antifungal [10], antimalarial [11], antiplasmodium [12] and anticancer [13,14] effects. After completion of the reaction (monitored by TLC) and cooling, the solid formed was filtered off, washed with dilute cold ethyl alcohol and recrystallized from ethyl alcohol to give compound 2. After completion of the reaction (monitored by TLC) and cooling, the solid formed was filtered off, washed with dilute cold ethyl alcohol and recrystallized from ethyl alcohol to yield compound 3. 10 μL of Premixed WST-1 Cell Proliferation Reagent was added to each well after drug incubation for 48 h and absorbance was measured 4 h later at 450 nm using Perkin Elmer Victor 1530 plate reader.
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