Synthesis of 6-Azapurines by Transformation of Toxoflavins and Reumycins (7-Azapteridines) and their Cytotoxicities

Jun Ma; Fumio Yoneda; Tomohisa Nagamatsu

doi:10.1071/CH14425

RESEARCH FRONT

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Synthesis of 6-Azapurines by Transformation of Toxoflavins and Reumycins (7-Azapteridines) and their Cytotoxicities

Jun Ma ^A , Fumio Yoneda ^B and Tomohisa Nagamatsu ^A ^C ^D

+ Author Affiliations

- Author Affiliations

^A Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima-naka, Okayama 700-8530, Japan.

^B Fujimoto Pharmaceutical Co., Ltd, Matsubara, Osaka 580-0011, Japan.

^C Kumamoto Health Science University, Department of Medical Technology, Faculty of Health Science, 325 Izumimachi, Kita-ku, Kumamoto City, Kumamoto 861-5598, Japan.

^D Corresponding author. Email: nagamatu@kumamoto-hsu.ac.jp

Australian Journal of Chemistry 68(2) 203-210 https://doi.org/10.1071/CH14425
Submitted: 29 June 2014 Accepted: 22 July 2014 Published: 5 November 2014

Abstract

This paper describes a reliable and facile synthesis of 6-azapurines, 1,5-dimethyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-ones and 5-methyl-5H-imidazo[4,5-e][1,2,4]triazin-6(7H)-ones, by treatment of toxoflavins and reumycins with 10 % aqueous or ethanolic sodium hydroxide at 5–70°C or reflux, followed by decarboxylation and oxidation by air along with a benzilic acid type rearrangement. Furthermore, heating the produced 6-azapurines in 10 % ethanolic sodium hydroxide afforded the corresponding 1-methyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazines with 1-methylurea. The antitumour activities of the 6-azapurines against CCRF-HSB-2 (human T-cell acute lymphoblastoid leukemia) and KB (human oral epidermoid carcinoma) cell lines were also investigated in vitro and some of the compounds showed prospective antitumour activities.

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Synthesis of 6-Azapurines by Transformation of Toxoflavins and Reumycins (7-Azapteridines) and their Cytotoxicities

Abstract

References

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