23060-85-7

Basic information

• Product Name: 4H-Pyran-4-thione,3-hydroxy-2-methyl-(8CI,9CI)
• Synonyms: 4H-Pyran-4-thione,3-hydroxy-2-methyl-(8CI,9CI)
• CAS NO: 23060-85-7
• Molecular Formula: C₆H₆O₂S
• Molecular Weight: 142.17564
• Product Categories: THIOL
• Mol File: 23060-85-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-Pyran-4-thione,3-hydroxy-2-methyl-(8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyran-4-thione,3-hydroxy-2-methyl-(8CI,9CI)(23060-85-7)
• EPA Substance Registry System: 4H-Pyran-4-thione,3-hydroxy-2-methyl-(8CI,9CI)(23060-85-7)

Safety Data

• Hazardous Substances Data: 23060-85-7(Hazardous Substances Data)

Usage

Uses

Thiomaltol was shown as a promising lead compounds for the development of slow-binding inhibitor of Bacillus anthracis.

Upstream product

• 1223525-45-8 2-methyl-4H-pyran-4-thione-3-β-D-glucopyranoside 
• 546-88-3 acetylhydroxamic acid 
• 118-71-8 Maltol 

Downstream Products

• 1043932-31-5 C₉H₉ClO₃S 
• 1043933-19-2 C₈H₇ClO₃S 
• 1383484-20-5 1-((3',4'-difluoro-[1,1'-biphenyl]-4-yl)methyl)-3-hydroxy-2-methylpyridine-4(1H)-thione 
• 52614-55-8 [Zn(3-hydroxy-2-methyl-4H-pyran-4-thione)₂] 

Relevant articles and documents

Biologically relevant O,S-donor compounds. Synthesis, molybdenum complexation and xanthine oxidase inhibition

Two O,S-donor ligands, hydroxythiopyrone and hydroxythiopyridinone derivatives, were developed and studied, as well as the corresponding O,O-derivatives, with a view to their potential pharmacological applications as xanthine oxidase (XO) inhibitors. The biological assays revealed that the O,S-ligands present high inhibitory activity towards XO (nanomolar order, close to that of the pharmaceutical drug allopurinol), in contrast to the corresponding O,O-analogues. Due to the biomedical relevance of this molybdenum-containing enzyme, the corresponding Mo(vi) complexes were studied both in solution and in the solid state, aimed at identifying the source of the biological properties. The solution studies showed that, in comparison with the O,O-analogues, the Mo(vi) complexes with the O,S-ligands present some stabilization, which is even more pronounced for the reduced Mo(iv) species. The crystal structures of the Mo(vi) complexes with the hydroxythiopyrone revealed good flexibility of the coordination modes, with two structural isomers and two polymorphic forms for a mononuclear and a binuclear species, respectively. These results give some support to mechanistic proposals for the XO inhibition involving the interaction of the thione group with the molybdenum cofactor, thus indicating a role of the sulfur atom in the XO inhibition. The Royal Society of Chemistry.

Maltol-derived ruthenium-cymene complexes with tumor inhibiting properties: The impact of ligand-metal bond stability on anticancer activity in vitro

Organometallic rutheniumarene compounds bearing a maltol ligand have been shown to be nearly inactive in in vitro anticancer assays, presumably due to the formation of dimeric Ru" species in aqueous solutions. In an attempt to stabilize such complexes, [Ru(i6-p-cymene)(XY)Cl] (XY = pyrones or thiopyrones) complexes with different substitution pattern of the (thio)pyrone ligands have been synthesized, their structures char-acterized spectroscopically, and their aquation behavior investigated as well as their tumor-inhibiting potency. The aquation behavior of pyrone systems with electron-donating substituents and of thiopyrone complexes was found to be significantly different from that of the maltol-type complex reported previously. However, the formation of the dimer can be excluded as the primary reason for the inactivity of the complex because some of the stable compounds are not active in cancer cell lines either. In contrast, studies of their reactivity towards amino acids demonstrate different reactivities of the pyrone and thiopyrone complexes, and the higher stability of the latter probably renders them active against human tumor cells.

Anti-diabetic effect of organo-chalcogen (sulfur and selenium) zinc complexes with hydroxy-pyrone derivatives on leptin-deficient type 2 diabetes model ob/ob mice

Since the discovery of the anti-diabetic effects of zinc (Zn) complex, we synthesized several Zn complexes and evaluated their effects using the KKAy type 2 diabetes mouse model. Recently, we demonstrated that organo-chalcogen (sulfur and selenium) Zn complexes elicit strong anti-diabetic effects. In this study, we treated leptin-deficient ob/ob mice with organo-chalcogen Zn complexes, and evaluated the resulting anti-diabetic effects in a mouse model of diabetes arising from pathogenic mechanisms different from those in KKAy mice. C57BL/6J ob/ob mice orally received either bis(3-hydroxy-2-methyl-4(H)-pyran-4-thiono)Zn, [Zn(hmpt)2] or bis(3-hydroxy-2-methyl-4(H)-pyran-4-seleno)Zn, [Zn(hmps)2], daily for 28 days. Both Zn complexes elicited potent blood glucose-lowering effects and improved HbA1c values. Moreover, glucose intolerance improved as evidenced by the oral glucose tolerance test, and fasting plasma insulin levels decreased in both types of Zn complex-treated mice. Zn concentrations in the liver and pancreas of [Zn(hmpt)2]-treated mice and in the pancreas of [Zn(hmps)2]-treated mice were increased, respectively. The results suggest that the present Zn complexes mainly exerted an anti-diabetic effect in the liver or pancreas. This study is the first to demonstrate that potent Zn complexes elicit anti-diabetic effects in not only KKAy but also ob/ob mice via a normalizing effect on insulin secretion and fasting blood glucose levels.

Enzymatic activation of a matrix metalloproteinase inhibitor

Matrix metalloproteinase inhibitors (MMPi) possessing a glucose protecting group on the zinc-binding group (ZBG) show a dramatic increase in inhibitory activity upon cleavage by β-glucosidase.