Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2019 Dec;34(1):1722-1729.
doi: 10.1080/14756366.2019.1670657.

Synthesis, cytotoxicities, and carbonic anhydrase inhibition potential of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

Sinan Bilginer  1 , Halise Inci Gul  1 , Feyza Sena Erdal  1 , Hiroshi Sakagami  2 , Serkan Levent  3 , Ilhami Gulcin  4 , Claudiu T Supuran  5
Affiliations

Synthesis, cytotoxicities, and carbonic anhydrase inhibition potential of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

Sinan Bilginer et al. J Enzyme Inhib Med Chem. 2019 Dec.

Abstract

In this study, new chalcone compounds having the chemical structure of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones (1-8) were synthesised and were characterised by 1H-NMR, 13 C-NMR, and HRMS spectra. Cytotoxic and carbonic anhydrase (CA) inhibitory effects of the compounds were investigated. Cytotoxicity results pointed out that compound 4, 6-[3-(4-trifluoromethylphenyl)-2-propenoyl]-3H-benzoxazol-2-one, showed the highest cytotoxicity (CC50) and potency-selectivity expression (PSE) value, and thus can be considered as a lead compound of this study. According to the CA inhibitory results, IC50 values of the compounds 1-8 towards hCA I were in the range of 29.74-69.57 µM, while they were in the range of 18.14 - 48.46 µM towards hCA II isoenzyme. Ki values of the compounds 1-8 towards hCA I were in the range of 28.37 ± 6.63-70.58 ± 6.67 µM towards hCA I isoenzyme and they were in the range of 10.85 ± 2.14 - 37.96 ± 2.36 µM towards hCA II isoenzyme.

Keywords: Anticancer; benzoxazolone; carbonic anhydrase; chalcone; cytotoxic.

PubMed Disclaimer

Figures

Scheme 1.
Scheme 1.
Synthesis of the compounds 1–8. Ar: Phenyl (1); 4-methylphenyl (2); 4-Methoxyphenyl (3); 4-trifluoromethylphenyl (4); 3-hyrdoxyphenyl (5); 4-isopropylphenyl (6); 4-dimethylaminophenyl (7); 4-benzyloxyphenyl (8).
Figure 1.
Figure 1.
The details of 1H-NMR spectra of compound 2 as represantative 1H-NMR. δ (ppm) Ha: 8.05 (dd, 1H, JHa-Hb: 8.1 Hz, JHa-Hc: 1.5 Hz), Hb: 7.22 (d, 1H, JHa-Hb: 8.1 Hz), Hc: 8.08 (d, 1H, JHa-Hc: 1.5 Hz), Hd: 7.79 (d, 2H, JHd-He: 8.0 Hz), He: 7.27 (d, 2H, JHd-He: 8.0 Hz), Hα: 7.93 (d, 1H, JHα-Hβ: 15.5 Hz), Hβ: 7.70 (d, 1H, JHα-Hβ: 15.5 Hz) CH3 protons: 2.35 (s, 3H).
See this image and copyright information in PMC

References

    1. Ferlay J, Colombet M, Soerjomataram I, et al. Estimating the global cancer incidence and mortality in 2018: GLOBOCAN sources and methods. Int J Cancer 2019;144:1941–1953. - PubMed
    1. Raghavendra NM, Pingili D, Kadasi S, et al. Dual or multi-targeting inhibitors: the next generation anticancer agents. Eur J Med Chem 2018;143:1277–300. - PubMed
    1. Ashby J. Potential carcinogenicity of alkylating agents. Chem Brit 1978;14:595.
    1. Gul HI, Cizmecioglu M, Zencir S, et al. Cytotoxic activity of 4′-hydroxychalcone derivatives against Jurkat cells and their effects on mammalian DNA topoisomerase I. J Enzyme Inhib Med Chem 2009;24:804–7. - PubMed
    1. Erciyas E, Erkaleli HI, Cosar G. Antimicrobial evaluation of some styryl ketone derivatives and related thiol adducts. J Pharm Sci 1994;83:545–8. - PubMed

MeSH terms

LinkOut - more resources