79246-92-7Relevant academic research and scientific papers
Synthesis of metal complexes with 1-substituted 3-hydroxy-2(1H)-pyridinethiones and their insulin-mimetic activities
Katoh, Akira,Yokoyama, Hiroko,Matsumura, Yuriko,Yoshikawa, Yutaka,Yasui, Hiroyuki,Sakurai, Hiromu
experimental part, p. 585 - 600 (2010/09/07)
Eight kinds of 1-alkyl-3-hydroxy-2(1H)-pyridinethiones were synthesized from a commercially available 3-methoxy-2(1H)-pyridinone via 3 steps. Zn(II) and vanadyl complexes were synthesized by treatment with Zn(OAc)2 or ZnSO4, and VOSO4, respectively. Vanadyl complexes were found to exist in VO(S2O2) coordination mode by means of ESR spectroscopy. From in vitro evaluation of the inhibitory effect on FFA release from rat adipocytes treated with epinephrine, it was found that IC50 values of Zn(II) complexes with 1-alkyl-3-hydroxy-2(1H)-pyridinethiones, regardless of the methylene-chain length at N-1 position, were in micromolar levels. In other words, these Zn(II) complexes showed higher insulin-mimetic activities than those synthesized previously. On the other hand, the insulin-mimetic activity of vanadyl complexes unfortunately could not be measured owing to their insolubility in KRB buffer which is used in vitro assay.
ZINC-BINDING GROUPS FOR METALLOPROTEIN INHIBITORS
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Page/Page column 6/15, (2008/06/13)
The present invention relates to metalloprotein inhibitors comprising: a. an organic backbone molecule (Pep) and at least one zinc binding group (ZBG) covalently attached thereto; or b. at least one ZBG substituted by a side chain that comprises one or more amido and/or amino moieties, wherein the ZBG is of formula (I): wherein the wavy line represents a Pep molecule or a side chain that is an R3 or an R4 group which comprises one or more amido and/or amino moieties, and wherein X is O or S and each R1, R2, R3, and R4 is individually hydrogen or an organic radical. The metalloprotein inhibitors are useful for preventing or treating a pathological disease, condition, or symptom that is associated with pathological metalloprotein activity and/or that is alleviated by inhibition of said activity.
1,3-Dipolar Character of Six-membered Aromatic Rings. Part 55. 3-Hydroxypyridine-2-thiones: Betaines, Cycloadditions, and Other Reactions
Katritzky, Alan R.,Grzeskowiak, Nicholas E.
, p. 2345 - 2389 (2007/10/02)
1-Methyl-2-methylthio-3-oxidopyridinium, 2-allylthio-1-methyl-3-oxidopyridinium, and 1--2-methylthio-3-oxidopyridinium undergo 1,3-dipolar cycloaddition to electron-deficient alkenes giving azabicyclooctene adducts having 1-alkylthio substituents.Quaternisation and tropone formation are investigated. 3-Hydroxypyridine-2-thione is cycloalkylated between sulphur and oxygen by substituted 1,1-dichloromethanes and certain α-haloacetyl chlorides. 1-(2-Pyridylmethyl)-3-oxidopyridinium gives azabicyclooctene cycloadducts with electron-deficient alkenes.The stereochemistry of all cycloadducts is deduced from the n.m.r.spectra.
