Inhibitory activity of benzo[h]quinoline and benzo[h]chromene in human glioblastoma cells
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
Submission of a manuscript to this journal is a representation that the manuscript has not been published previously and is not under consideration for publication elsewhere.
All authors named in each manuscript would be required to sign a form (to be supplied by the Editor) so that they may retain their copyright in the article but to assign to us (the Publishers) and its licensees in perpetuity, in all forms, formats and media (whether known or created in the future) to (i) publish, reproduce, distribute, display and store the contribution, (ii) translate the contribution into other languages, create adaptations, reprints, include within collections and create summaries, extracts and/or abstracts of the contribution, (iii) create any other derivative works(s) based on the contribution, (iv) to exploit all subsidiary rights in the contribution, (v) the inclusion of electronic links from the contribution to third party material where-ever it may be located, and (vi) license any thrid party to do any or all of the above.