The Synthesis and Testing of α-(Hydroxymethyl)pyrroles as DNA Binding Agents

Derek C. Martyn; Andrew D. Abell

doi:10.1071/CH04183

RESEARCH ARTICLE

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The Synthesis and Testing of α-(Hydroxymethyl)pyrroles as DNA Binding Agents

Derek C. Martyn ^A and Andrew D. Abell ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.

^B Corresponding author. Email: andrew.abell@canterbury.ac.nz

Australian Journal of Chemistry 57(11) 1073-1077 https://doi.org/10.1071/CH04183
Submitted: 30 July 2004 Accepted: 21 September 2004 Published: 1 November 2004

Abstract

The α-(hydroxymethyl)pyrroles 16a and 16b were prepared and shown to be cytotoxic against the P388 cancer cell line. Ethyl 5-hydroxymethyl-1H-pyrrole-2-carboxylate 18 was inactive, demonstrating that an α-(hydroxymethyl)pyrrole group alone is not sufficient for activity. Compound 16b has been shown to bind to DNA with reasonable affinity.

Acknowledgments

The authors thank Professor Bruce Baguley (Auckland Cancer Society Research Centre) for performing the DNA binding assays, and Gill Ellis (Marine Natural Products Group, Department of Chemistry, University of Canterbury) for carrying out the P388 cytotoxicity assays. Financial support from Bright Futures Top Achievers Doctoral Scholarship (D.C.M.) and the Royal Society of New Zealand Marsden Fund is also gratefully acknowledged.

References

The Synthesis and Testing of α-(Hydroxymethyl)pyrroles as DNA Binding Agents

Abstract

Acknowledgments

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