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New route for synthesis, spectroscopy, and X-ray studies of 2-[aryl-(6′-hydroxy-4′,4′-dimethyl-2′-oxocyclohex-6′-enyl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone and 1,8-dioxo-octahydroxanthenes and antitumor evaluation

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Abstract

Treatment of 1-(benzothiazol-2-yl-thio)-acetonitrile 1 with 5,5-dimethyl-1,3-cyclohexanedione-(dimedone) 2 and aromatic aldehyde 3a, b in refluxing ethanol containing a catalytic amount of piperidine lead to bisdimedone derivatives 5a and b in short periods of times with excellent yields and not 4H-chromen-5(6H)-one derivatives 8. The compound 5a was then cyclized to 1,8-dioxo-octahydroxanthene derivative 6. The structures of the synthesized compounds were elucidated by elemental analysis 1H NMR and 13C NMR spectra, COSY, HSQC, HMBC, MS, and X-ray crystallographic investigations. The cytotoxicity of the synthesized compounds 5a, b, and 6 were studied and evaluated. Three human tumor and three normal cell lines, namely as breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268), human fibroblast (WI-38), normal prostate epithelial cells, and normal colon mucosal, NCM 460 cells, respectively. The tested compounds were found to exhibit higher inhibitory effects toward the tumor and normal cell lines than the reference drug, doxorubicin.

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Acknowledgments

This work was financed by the University of Kuwait research Grant SC02/08. We are grateful to the Faculty of Science, Chemistry Department, SAF facility for the spectral and analytical data (Project GS01/01, GS03/08, GS01/03).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 12613, 13060, Safat, Kuwait

    Fatima Al-Omran & Adel Abou El-Khair

  2. Department of Chemistry, Faculty of Science, Cairo University, Cairo, Egypt

    Rafat M. Mohareb

Authors
  1. Fatima Al-Omran
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  2. Rafat M. Mohareb
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  3. Adel Abou El-Khair
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Correspondence to Fatima Al-Omran.

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Al-Omran, F., Mohareb, R.M. & El-Khair, A.A. New route for synthesis, spectroscopy, and X-ray studies of 2-[aryl-(6′-hydroxy-4′,4′-dimethyl-2′-oxocyclohex-6′-enyl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone and 1,8-dioxo-octahydroxanthenes and antitumor evaluation. Med Chem Res 23, 1623–1633 (2014). https://doi.org/10.1007/s00044-013-0712-3

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  • DOI: https://doi.org/10.1007/s00044-013-0712-3

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