Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives

Date

2019-11-01

Author

Khan, Rehan
Ulusan, Sinem
Banerjee, Sreeparna
Doğan, Özdemir

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New aziridine 2-phosphonic acids were prepared by monohydrolysis of the aziridine 2-phosphonates that were obtained by the modified Gabriel-Cromwell reaction of vinyl phosphonate or alpha-tosylvinyl phosphonate with a primary amine or a chiral amine. The cellular cytotoxicity of these compounds was tested against the HCT-116 colorectal cancer cell lines and the CCD-18Co normal colon fibroblast lines using the MTT assay. Three of the synthesized phosphonic acid derivatives 2e (ethyl hydrogen {(2S)-1-[(1S)-1-(naphthalen-2-yl)ethyl]aziridin-2-yl}phosphonate), 2h (ethyl hydrogen (1-benzylaziridin-2-yl)phosphonate), and 2i (ethyl hydrogen (1-cyclohexylaziridin-2-yl)phosphonate) showed higher cytotoxicity than the reference cancer treatment agent etoposide. Cell death was through a robust induction of apoptosis even more effectively than etoposide, a well-known apoptosis inducing agent.

Subject Keywords

Molecular Medicine, Biochemistry, Bioengineering, General Chemistry, Molecular Biology, General Medicine

URI

https://hdl.handle.net/11511/42576

Journal

CHEMISTRY & BIODIVERSITY

DOI

https://doi.org/10.1002/cbdv.201900375

Collections

Department of Chemistry, Article

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Citation Formats

R. Khan, S. Ulusan, S. Banerjee, and Ö. Doğan, “Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives,” CHEMISTRY & BIODIVERSITY, pp. 0–0, 2019, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42576.