1-n-Propyl- and 1-n-butyl-3-hydroxy-2-methyl-4-pyridinone complexes of group 13 (IIIA) metal ions

Abstract

. Can. J. Chem. 69, 893 (1991). The aluminum, gallium, and indium tris(1igand) complexes of 3-hydroxy-2-methyl-1-n-propyl-4-pyridinone and l-tz-butyl-3-hydroxy-2-methyl-4-pyridinone have been prepared and characterized. All six compounds were prepared in a one-pot synthesis from maltol, n-propyl-, or n-butylamine and an appropriate metal(II1) salt, and were completely characterized (IR, FAB-MS, 'H NMR, ' '~1 NMR, elemental analysis). Three of the six complexes were studied by single-crystal X-ray diffraction and were found to form trihydrates, unlike their 1-methyl and 1-ethyl analogues, which formed dodecahydrates. The n-butylpyridinone complex A1(CIOH14N02)3.3H20 (Al(nbp)3.3H2O) and 11-propylpyridinone complexes A1(C9H12N02)3.3H20 (A l ( n~p )~. 3 H~O ) , and Ga(C9H12N02)3.3H20 ( G a ( n p~)~. 3 H~O ) were essentially isostructural, crystallizing in the space group On a prCparC et caractiris6 les complexes tricoordinks de l'aluminium, du galliumet de l'indium avec la 3-hydroxy-2-mkthyll-n-propyl~pyridin-4-one et la 1-11-butyl-3-hydroxy-2-mithyl-pyridin-4-On a prepare les six composCs par des synthkses "bouillabaisses" impliquant le maltol, les tz-propyl-ou n-butyl-amines et le sel mCtallique(II1) appropriC et on les a caractCrisks compl&tement par ir, sm-bar, rmn du 'H, rmn du "Al et analyse ClCmentaire. On a examine trois des six complexes par diffraction des rayons-X par des cristaux uniques et on a trouvC qu'ils forment des trihydrates alors que leurs analogues I-mkthyle et 1-Cthyle foment des dodCcahydrates. Le complexe de la n-butylpyridinone, A1(CloH14N02)3.3H20 ( A l ( n b~)~. 3 H~O ) et les complexes de la n-propylpyridinone, A1(C9H12N02)3.

A new bis(3-hydroxy-4-pyridinone)-IDA derivative as a potential therapeutic chelating agent. Synthesis, metal-complexation and biological assays

“…pH 5.57) should be attributed to a complex with octahedral geometry around the aluminium. Although this chemical shift is close to that reported for a tris-hydroxypyridonate coordination (d = 37 ppm, W 1/2 = 920 Hz), 28 such a complete hydroxypyridinonate coordination cannot be considered for an Al-bis-hydroxypyridinone system at 1 : 1 metal-to-ligand molar ratio. However, these spectral data can be ascribed to an octahedral di-bridged di-(hydroxo-ligand-Al) [Al 2 (OH) 2 L 2 ] complex, according to the proposed speciation model.…”

Synthesis, physicochemical properties, and biological evaluation of N-substituted 2-alkyl-3-hydroxy-4(1H)-pyridinones: orally active iron chelators with clinical potential

“…Analogous procedures using a range of primary and secondary amines gave compounds 38 to 44 in Table X. l-Decyl-2-methyl-3-hydroxy-4-(lfl)-pyridinone Hydrochloride (28). To a solution of 5 (25 g, 0.12 mol) in ethanol (200 mL)/water (200 mL) was added decylamine (29 g, 0.18 mol) followed by 2 N sodium hydroxide solution (10 mL) and the mixture refluxed for 18 h. After adjustment to pH 1 with hydrochloric acid solvent was removed by rotary evaporation to give a red oil, which was reconstituted in ethanol (360 mL)/water (40 mL) and subjected to hydrogenolysis for 4 h in the presence of 5% Pd/C catalyst (1 g).…”

Synthesis and hydroboration of lipophilic hydroxy-pyridinones and their complexes with molybdenum(VI)

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] For example, hdmp ( Fig. 1) has found moderate success in chelation therapy for the treatment of iron-overload in humans.…”