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 May;26(4):673-680.
doi: 10.1016/j.sjbs.2017.12.007. Epub 2017 Dec 24.

Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives

Ibrahim A Arif  1 , Anis Ahamed  1 , Radhakrishnan Surendra Kumar  2 , Akbar Idhayadhulla  2 , Aseer Manilal  3
Affiliations

Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives

Ibrahim A Arif et al. Saudi J Biol Sci. 2019 May.

Abstract

The objective of this study was to investigate brine shrimp cytotoxicity, larvicidal, nematicidal, and antifeedant activities of novel piperidin-connected 2-thioxo-imidazolidin-4-one derivatives. The activities of target compounds were compared with some naturally occurring (-)-pinidinol, hydantocidin, and positive controls. Target compounds were synthesized via cyclocondensation method. The compounds were synthesized and then characterized by infrared spectroscopy, 1H NMR, 13C NMR, mass spectral, and elemental analyses. Brine shrimp cytotoxicity assay was investigated using freshly hatched, free-swimming nauplii of Artemiasalina. Larvicidal screening was performed against urban mosquito larvae (Culex quinquefasciatus). Nematicidal activity was evaluated using juvenile nematodes of Meloidogyne javanica. Regarding antifeedant activity, marine-acclimated Oreochromis mossambicus fingerlings were used. Compounds 3a-c (piperidin-connected 2-thioxoimidazolidin-4-one) were found to be lethal to the second instar larvae of mosquito, which produced LD50 values of 1.37, 6.66, 6.51 μg/mL, compared to compounds (-) pinidinol and hyantocidin LD50 values of 18.28 and 22.11 μg/mL respectively. Compound 3a-c was found to kill 100% of fish fingerlings within 6 h at 20 µg/mL, with LD50 values of 1.54, 1.79, 1.52 µg/mL, compared to compounds (-) pinidinol and hyantocidin with LD50 values of 10.21 and 21.05 μg/mL respectively. Compound 3c with LD50 value of 1.57 μg/mL demonstrated high nematicidal activity compared to compound 3a, 3b, (-) Pinidinol and Hyantocidin LD50 values of 6.45, 2.42, 14.25, 26.30 μg/mL respectively. Therefore, the 2-thioxoimidazolidin-4-one with piperidin ring showed high potential cytotoxic, larvicidal, nematicidal, and antifeedent activities.

Keywords: 2-thioxoimidazolidin-4-one; Antifeedant activity; Brine shrimp cytotoxicity; Larvicidal activity; Nematicidal activity.

PubMed Disclaimer

Figures

Fig. 1
Fig. 1
Natural piperidine and imidazolidin-2,4-dione bioactive compounds.
Scheme 1
Scheme 1
Synthesis of 2-thio-imidazolidin-4-one derivatives 1a-c, 2a-c, and 3a-c.
Fig. 2
Fig. 2
Bioassay screening of synthesized compounds (1a-c, 2a-c, and 3a-c).
See this image and copyright information in PMC

References

    1. Ahmed K.I. Synthesis of arylidenehydrazono–and glycol pyranosyl hydrazine sulfonyl benzylidene-2,4-imidazolidindionesas potential antiviral and antitumoral agents. Carbohydr. Res. 1998;306:567–573. - PubMed
    1. Andeson J.E. A blind comparison of simple bench-top bioassays aand human tumor cell cytotoxicities as antitumor prescreening. Phytochem. Anal. 1991;2:107–111.
    1. Argandona V.H., Rovirosa J., San-Martın A., Riquelme A., Diaz-Marrero A.R., Cueto M., Darius J., Santana O., Guadano A., Gonzalez-Coloma A. Antifeedant effects of marine halogenated monoterpenes. J. Agric. Food Chem. 2002;50:7029–7033. - PubMed
    1. Balasubramanian S., Ramalingam C., Kabilan S. Synthesis of some spiroheterocycles. Indian J. Chem. 2002;41B:2402–2404.
    1. Baliah V., Noller C.R. The preparation of some piperidine derivatives by the Mannich Reaction. J. Am. Chem. Soc. 1948;70:3853–3858. - PubMed