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Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives

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Abstract

Some dihydrobenzo[4,5]imidazo[1,2-c]quinazolines have been synthesized from aldehydes and ketones, using the ketones as both reagents and solvents and tetrahydrofuran (THF) as the solvent for the aldehydes, to yield the triazatetracyclics. The compounds have been characterized with spectroscopy and microanalysis. The crystal structures of 9,9-dimethyl-8,10,17-triazatetracyclo[8.7.02,7.011,16]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (I), 9-butyl-9-methyl-8,10,17-triazatetracyclo[8.7.0.02,7.011,16]heptadeca-(17),2,4,6,11(16),12,14-heptaene (III) and 9-phenyl-8,10,17-triazatetracyclo[8.7.0 02 7.011,16]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (VIII) have been discussed. The computed NMR, IR, molecular electrostatic potential and frontier molecular orbitals of compounds I, III and VIII have been discussed. The M06 functional gave most of its values closest to the experimental values for the bond lengths and bond angles of compounds I and III. For compound VIII, none of the functionals gave values for bond lengths and bond angles that were consistent with the experimental values, but M06 gave values closest to experimental values. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging activity of the triazatetracyclics showed that compound I exhibits significant DPPH scavenging activity with an IC50 of 56.18 µM compared to 2.37 µM for ascorbic acid.

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Acknowledgements

We thank MRC for the research funding (MRC-SIR). F. Odame thanks the National Research Foundation for awarding him a postdoctoral fellowship. We would also like to acknowledge the Center for High Performance Computing (CHPC) for allocation of resources (projects CHEM0802 and CHEM1261).

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Authors and Affiliations

  1. University of Health and Allied Sciences, PMB 31, Ho, Ghana

    F. Odame

  2. Department of Chemistry, Nelson Mandela University, P.O. Box 77000, Port Elizabeth, 6031, South Africa

    F. Odame, Eric C. Hosten, R. Betz & Zenixole R. Tshentu

  3. Department of Biochemistry and Microbiology, Nelson Mandela University, P.O. Box 77000, Port Elizabeth, 6031, South Africa

    J. Krause & Carminita L. Frost

  4. Department of Chemistry, Rhodes University, P.O. Box 94, Grahamstown, 6140, South Africa

    K. Lobb

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  1. F. Odame
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Supplementary Information

Supplementary data associated with this article can be found, in the online version. CCDC numbers 1052183, 1051981 and 1051826 contain the crystal structures associated with this article. Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 27977kb)

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Odame, F., Hosten, E.C., Betz, R. et al. Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives. J IRAN CHEM SOC 18, 1979–1995 (2021). https://doi.org/10.1007/s13738-021-02158-3

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  • DOI: https://doi.org/10.1007/s13738-021-02158-3

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