7666-04-8

Usage

Uses

Used in Pharmaceutical Industry:
2-(Methylthio)imidazole is used as a reagent for the synthesis of 4-Methyl-5-phenyl-(1,2,4)-triazoles, which are selective inhibitors of 11β-hydroxysteroid dehydrogenase type I (11β-HSD1). This enzyme plays a crucial role in the regulation of glucocorticoid hormones, and its inhibition can have therapeutic benefits in treating various metabolic and inflammatory disorders. The use of 2-(Methylthio)imidazole in the synthesis of these triazoles contributes to the development of potential drug candidates for such applications.

InChI:InChI=1/C4H6N2S/c1-7-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)

Upstream product

• 872-35-5 imidazole-2-thione 
• 93-58-3 benzoic acid methyl ester 
• 57332-70-4 methyl 2-thioxo-1,3-dihydroimidazole-4-carboxylate 
• 17157-48-1 bromoacetaldehyde 
• 20112-79-2 2-methylthioimidazoline 
• 872-35-5 1,3-dihydro-imidazole-2-thione 
• 74-88-4 methyl iodide 
• 2524-03-0 dimethyl chlorothiophosphate 

Downstream Products

• 872-35-5 imidazole-2-thione 
• 1042443-41-3 C₂₃H₂₁Cl₂N₅S 
• 1092852-05-5 1-(2-methylthio-1H-imidazol-1-yl)-4-phenyl-2-butanone 
• 763077-18-5 1H-Imidazole, 1-[[1-(4-chloro-3-methylphenyl)-1H-imidazol-4-yl]methyl]-2-(methylthio)- 

Relevant academic research and scientific papers

SUBSTITUTED IMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted imidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

OXAZOLE AND THIAZOLE DERIVATIVES AS SELECTIVE PROTEIN KINASE INHIBITORS (C-KIT)

The present invention relates to compounds of formula I or pharmaceutically acceptable salts thereof: wherein R1, R2, R3, A, Q, W and X are as defined in the description. These compounds selectively modulate, regulate, and/or inhibit signal transduction mediated by certain native and/or mutant proteine kinases implicated in a variety of human and animal diseases such as cell proliferative, metabolic, allergic, and degenerative disorders. More particularly, these compounds are potent and selective native and/or mutant c-kit inhibitors.

5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE COMPOUNDS

The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine derivatives of formula (I) wherein R1, R2, R3, and R4 are as described n the description, to salts, especially pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments; especially as orexin receptor antagonists.

Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases

Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising biotransformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions. Copyright

5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE COMPOUNDS

The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5- a]pyrazine derivatives of formula (I) wherein R1, R2, R3, and R4 are as described n the description, to salts, especially pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments; especially as orexin receptor antagonists.

2-ARYLTHIAZOLE DERIVATIVES AS CXCR3 RECEPTOR MODULATORS

The invention encompasses compounds of Formula I or pharmaceutically acceptable salts thereof, which are modulators of the CXCR3 chemokine receptor function useful for the treatment or prevention of pathogenic inflammatory processes, autoimmune diseases or graft rejection processes. Methods of use and pharmaceutical compositions are also encompassed.

o-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates: Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane Deprotections

o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found to be readily accessible under notably mild conditions. Further investigation of these transformations led to the elucidation of valuable mechanistic details, resulting in the conclusion that they proceed via ionic rather than single electron transfer (SET) pathways.

New reactions of IBX: Oxidation of nitrogen- and sulfur-containing substrates to afford useful synthetic intermediates

New reactions for the synthetic toolbox: 2-lodoxybenzoic acid (IBX) was employed to access a diverse array of useful synthetic intermediates. Among other transformations, the developed chemistry converts amines into imines, dithianes into carbonyl groups, N-heterocycles into N-heteroaromatic compounds, and hydroxylamines into oximes in high yields.

An Unusual S- and N-Alkylation of Mercapto Substituted Heterocycles with O,O-Dialkyl Chlorophosphate/Thiophosphate

The reaction of different mercapto substituted heterocycles with O,O-dialkyl chlorophosphate or thiophosphates, gave the corresponding S- and N- alkylated derivatives instead of the expected phosphorylated products.