Design, synthesis and in vitro anticancer evaluation of 4,6-diamino-1,3,5-triazine-2-carbohydrazides and -carboxamides

Kothayer, Hend, Elshanawani, Abdalla A., Abu Kull, Mansour E., El-Sabbagh, Osama I., Shekhar, Malathy P. V., Brancale, Andrea ORCID: https://orcid.org/0000-0002-9728-3419, Jones, Arwyn Tomos ORCID: https://orcid.org/0000-0003-2781-8905 and Westwell, Andrew D. ORCID: https://orcid.org/0000-0002-5166-9236 2013. Design, synthesis and in vitro anticancer evaluation of 4,6-diamino-1,3,5-triazine-2-carbohydrazides and -carboxamides. Biorganic and Medicinal Chemistry Letters 23 (24) , pp. 6886-6889. 10.1016/j.bmcl.2013.09.087

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Abstract

Series of substituted 4,6-diamino-1,3,5-triazine-2-carbohydrazides and -carboxamides have been synthesised, based on molecular modelling of candidate structures related to the previously reported Rad6B-inhibitory diamino-triazinylmethyl benzoate anticancer agents TZ8 and TZ9. Synthesis of the target compounds was readily accomplished in two steps from aryl biguanides via reaction of phenylhydrazine or benzylamines with key 4-amino-6-(arylamino)-1,3,5-triazine-2-carboxylate intermediates. These new triazine derivatives were tested for in vitro anticancer activity against the Rad6B expressing human breast cancer cell lines MDA-MB-231 and MCF-7. Active compounds, such as the triazinyl-carbohydrazides 3a–e, were found to exhibit low micromolar IC50 values particularly in the Rad6B-overexpressing MDA-MB-231 cell line.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Pharmacy
Subjects:	R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer) R Medicine > RS Pharmacy and materia medica
Uncontrolled Keywords:	E2 ubiquitin conjugating enzyme; Rad6B; Triazines; Breast cancer; MDA-MB-231; MCF-7
Publisher:	Elsevier
ISSN:	0960-894X
Last Modified:	05 Jan 2024 05:54
URI:	https://orca.cardiff.ac.uk/id/eprint/56812

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