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Research Article

Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one and evaluation of their cytotoxicities

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Pages 818-823 | Received 11 Feb 2015, Accepted 25 Jun 2015, Published online: 06 Aug 2015
 

Abstract

Chalcones and Mannich bases are a group of compounds known for their cytotoxicities. In this study restricted chalcone analogue, compound 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one MT1, was used as a starting compound to synthesize new mono Mannich bases since Mannich bases may induce more cytotoxicity than chalcone analogue that they are derived from by producing additional alkylating center for cellular thiols. In this study, cyclic and acyclic amines were used to synthesize Mannich bases. All compounds were tested against Ca9–22 (gingival carcinoma), HSC-2, HSC-3 and HSC-4 (oral squamous cell carcinoma) as tumour cell lines and HGF (gingival fibroblasts), HPC (pulp cells) and HPLF (periodontal ligament fibroblasts) human normal oral cells as non tumour cell lines. Cytotoxicity, selectivity index (SI) values and potency selectivity expression (PSE) values expressed as a percentage were determined for the compounds. According to data obtained, the compound MT8 with the highest PSE value bearing N-methylpiperazine moiety seems to be a good candidate to develop new cytotoxic compounds and is suited for further investigation.

Declaration of interest

The authors report no conflict of interest. The authors alone are responsible for the content and writing of this article.

This research work was supported by Ataturk University Research Found, Turkey (Project No. BAP: 2010/166, 2011/289 and 2012/75). The authors are thankful to Dr Murat Sukuroglu (from Gazi University) for HRMS spectra and Ataturk University, Faculty of Science, Department of Organic Chemistry for NMR spectra.

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