β-Lactam-Synthon-Interceded Synthesis of Isatin–Imidazolidine-2-thione Conjugates with Structural Validation using Molecular Dynamic Simulations and Cytotoxic Evaluation

Parvesh Singh; Denver T. Hendricks; Krishna Bisetty; Vipan Kumar; Nisha

doi:10.1055/s-0033-1339315

Synlett, Table of Contents

Synlett 2013; 24(14): 1865-1869
DOI: 10.1055/s-0033-1339315

letter

β-Lactam-Synthon-Interceded Synthesis of Isatin–Imidazolidine-2-thione Conjugates with Structural Validation using Molecular Dynamic Simulations and Cytotoxic Evaluation

Nisha,

Parvesh Singh

^bDepartment of Chemistry, Durban University of Technology, Durban 4000, South Africa

,

Denver T. Hendricks

^cDivision of Medical Biochemistry, University of Cape Town, Anzio Road, Observatory 7925, South Africa

,

Krishna Bisetty

^bDepartment of Chemistry, Durban University of Technology, Durban 4000, South Africa

,

Vipan Kumar*

^aDepartment of Chemistry, Guru Nanak Dev University, Amritsar 143005, India Fax: +91(183)225881920 Email: vipan_org@yahoo.com

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Abstract

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Abstract

β-Lactam-synthon-interceded synthesis of isatin–imidazolidine-2-thione conjugates was carried out via base-assisted intermolecular amidolysis of 3-isothiocyanato-2-azetidinones with C-5 substituted isatins. The observed enolization in the assigned structure of the conjugates was validated using molecular dynamic (MD) simulations performed under explicit solvent conditions. The synthesized scaffolds were also evaluated for their cytotoxic profiles against the oesophageal cancer cell line WHCO1.

Key words

β-lactam synthon - imidazolidine-2-thione - intermolecular amidolysis - cytotoxicity - molecular dynamic simulations

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References

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