Lanthanide ions, Ln(III), are of interest in the treatment of bone density disorders because they are found to accumulate preferentially in bone (in vivo), have a stimulatory effect on bone formation, and exhibit an inhibitory effect on bone degradation (in vitro), altering the homeostasis of the bone cycle. In an effort to develop an orally active lanthanide drug, a series of 3-hydroxy-4-pyrid...

The quinone-methide elimination is a common, efficient methodology used in linkers designed to undergo self-fragmentation. Here, for the first time, we demonstrate this elimination in a pyridine ring system. Under physiological conditions, a compound constructed of a pyridine core, a reporter, and an enzymatic trigger underwent significantly faster 1,4-elimination than its parent compound with ...

In the title compound, C(15)H(14)N(2)OS, the pyridinone ring in the fused-ring system is nearly planar (r.m.s. deviation = 0.011 Å) and the cyclo-hexene ring has a twisted half-boat conformation with the methyl-ene C atom adjacent to the methine C atom deviating by 0.592 (7) Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.108 Å). The thienyl ring is disordered over tw...

Antibiotic G1549, isolated from culture broth of Pseudomonas alcaligenes, is a new cyclic hydroxamic acid with a 1-hydroxy-2(1H)-pyridinone structure that complexes with metals. The structure of G1549 is suggested to be 1-hydroxy-5-methoxy-6-methyl-2(1H)-pyridinone. In vitro, G1549 and its copper and ferric complexes show moderate activity against Gram-positive bacteria, fungi and Trichomonas v...

Glycosides of 3-hydroxy-4-pyridinones were synthesized and characterized by mass spectrometry, elemental analysis, (1)H and (13)C NMR spectroscopy, and in one case by X-ray crystallography. The Cu(2+) complex of a novel 3-hydroxy-4-pyridinone was synthesized and characterized by IR and X-ray crystallography, showing the ability of these compounds to chelate potentially toxic metal ions. An MTT ...

In the title compound, [Mo(C(5)H(4)NO(2))(2)O(2)], the Mo(VI) atom exhibits a distorted octa-hedral coordination geometry formed by two terminal oxo ligands and two monoanionic O,O-bidentate pyridinone ligands. The two terminal oxo ligands lie in a cis arrangement, the ketonic O atoms of the pyridinone ligands are coordinated trans to the oxo ligands and the deprotonated hydroxyl O atoms are lo...

Three cocrystals of the light-stable compound 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol (I) with light-sensitive molecules 1,2-dimethyl-2(1H)-pyridinone (a), 6-methyl-2(1H)pyridinone (b) and 2-methyl-2(1H)-pyridinone (c) were exposed to UV light. It was found that the molecules undergo molecular flip perpendicular to the molecular plane (rotation of ∼180°). In the first two cocrystals, the lig...

Lanthanide ions, Ln(III), are known functional mimics of Ca(II) ions and have been shown to affect the bone remodeling cycle. Exploiting this disruption to the bone remodeling cycle has potential for the treatment of bone density disorders, such as osteoporosis. In an effort to find new orally active agents for these disorders, a series of Ln(III) containing complexes incorporating small, non-t...

Three 3-hydroxymonoazine- and three N-hydroxydiazine-type heterocycles were tested whether they act as artificial siderophores toward Aureobacterium flavescens JG-9 (ATCC No. 25091). Among them, 1-hydroxy-3,5,6-trimethyl-2(1H)-pyrazinone (3) showed the highest growth-promotion activity comparable to desferrioxamine B (DFB), a natural trihydroxamate siderophore, at 48.5 microM or above, followed...

Twelve 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones were investigated by tandem mass spectrometry using positive as well as negative electrospray ionization. The influence of the electron affinity of the substituent and the steric effect on the fragmentation is discussed. Pyridinones with a substituent of low proton affinity show loss of water, HCN or benzene from the pyridinone ri...