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Communication | Special issue | Vol 79, No. 1, 2009, pp.411-415
Published online, 26th November, 2008
DOI: 10.3987/COM-08-S(D)53
Photo- and Electrochemical Properties of Novel 7-Substituted Naphthyridine Derivatives

Junya Chiba,* Yasuhiro Doi, and Masahiko Inouye*

*Laboratory of Chemical Biology, Faculty of Pharmaceutical Sciences, Toyama University, 2630 Sugitani, Toyama 930-0194, Japan

Abstract

Here we report a new class of 1,8-naphthyridine derivatives, 2-amino-7-(3,4-dimethoxyphenyl)-1,8-naphthyridine, 2-amino-7-(3,4-dihydroxy phenyl)-1,8-naphthyridine, 2-amino-(5,6-dimethoxy-1H-indenyl[2,3-b])-1,8- naphthyridine, and 2-amino-(5,6-dihydroxy-1H-indenyl[2,3-b])-1,8- naphthyridine. All of these compounds were synthesized via naphthyridine-ring forming reaction with 2,6-diaminopyridin-3-carboxaldehyde as a key step. The two dimethoxy derivatives showed predominant fluorescent emission around 400 nm in MeCN. Cyclic voltammetry of the two dihydroxy derivatives in phosphate buffer showed oxidation and reduction potentials around 0.23 and 0.13 V vs. Ag/AgCl, respectively.