23417-29-0

Usage

Uses

Used in Research and Development:
6-METHYL-1,3-BENZOXAZOLE-2-THIOL is used as a research chemical for [application reason], contributing to the advancement of scientific knowledge and the development of new technologies. Its unique structure and properties make it a valuable compound for studying various chemical reactions and processes.
Used in Pharmaceutical Industry:
6-METHYL-1,3-BENZOXAZOLE-2-THIOL is used as an intermediate or building block in the synthesis of pharmaceutical compounds for [application reason]. Its presence in the molecular structure of certain drugs can influence their chemical properties, stability, and potential therapeutic effects.
Used in Chemical Synthesis:
6-METHYL-1,3-BENZOXAZOLE-2-THIOL is used as a reagent or catalyst in various chemical synthesis processes for [application reason]. Its ability to participate in different types of reactions, such as oxidation, reduction, or substitution, makes it a versatile component in the production of a wide range of chemical products.
Used in Material Science:
6-METHYL-1,3-BENZOXAZOLE-2-THIOL is used as a component in the development of new materials for [application reason]. Its incorporation into the molecular structure of certain materials can enhance their properties, such as conductivity, stability, or reactivity, making them suitable for various applications in different industries.
Used in Environmental Applications:
6-METHYL-1,3-BENZOXAZOLE-2-THIOL is used as a component in environmental remediation processes for [application reason]. Its chemical properties can be harnessed to remove or neutralize pollutants, contributing to the development of more sustainable and eco-friendly solutions for environmental challenges.

InChI:InChI=1/C8H7NOS/c1-5-2-3-6-7(4-5)10-8(11)9-6/h2-4H,1H3,(H,9,11)

Upstream product

• 75-15-0 carbon disulfide 
• 2835-98-5 2-Hydroxy-4-methylanilin 
• 140-89-6 potassium ethyl xanthogenate 
• 128-04-1 sodium dimethyldithiocarbamate 
• 137-26-8 Thiram 

Downstream Products

• 213685-01-9 N-(2,6-diisopropylphenyl)-6-((6-methylbenzo[d]oxazol-2-yl)thio)hexanamide 
• 1378110-48-5 N-(2-(1-(6-methylbenzo[d]oxazol-2-yl)piperidin-4-yloxy)phenyl)-pyridine-2-sulfonamide 
• 3621-83-8 2-chloro-6-methylbenzo[d]oxazole 

Relevant academic research and scientific papers

Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media

A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o -aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C-S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol.

Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors

We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.

AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate

A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercapto benzoheterocycles (2-mercapto benzothiazoles, benzoxazoles and benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional molecules with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This novel synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple experimental procedures.

Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water

An efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-arylthiobenzoxazoles. Inexpensive metal catalyst and ligand, mild reaction temperature, and water as solvent make this protocol practically valuable and useful in organic synthesis.

An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water

An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.

Selective synthesis of 2-aminobenzoxazoles and 2-mercaptobenzoxazoles by using o-aminophenols as starting material

2-Aminobenzoxazoles and 2-mercaptobenzoxazoles were selectively synthesized by treating o-aminophenols with dithiocarbamates and tetramethylthiuram disulfide (TMTD), respectively. With the promotion of NaH/CuI, the reaction of o-aminophenols with dithioca

Regioselective thiolation of arenes and heteroarenes: C-H functionalization strategy for C-S bond formation

A facile transition-metal-free oxidative cross-dehydrogenative coupling reaction involving selective formation of a C-S bond leading to the synthesis of arylthiobenzoxazoles, heteroarylthiobenzoxazoles, and arylthiobenzothiazoles has been described. This highly regioselective C-H functionalization reaction with electron-rich aromatic systems including heteroaromatics is achieved by reversing the reactivity of sulfur in the presence of a suitable oxidant and strong acid. (Chemical Equation Presented).

DERIVATIVES OF HETEROARYLSULFONAMIDES, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPY

The present invention concerns derivatives of heteroarylsulfonamides, notably as blockers of Kv potassium channels, and more particularly of channels Kv1.5, Kv4.3 or Kv11.1, their application in clinical therapy and their preparation methods. These compounds correspond to the following general formula (I): where R1 represents one or more substituents of the phenyl core X such as: hydrogen, halogen, trifluoromethyl, trifluoromethoxy, linear or branched C1-C4 alkyl, or linear or branched C1-C4 alkoxy, A represents oxygen or sulphur, B represents nitrogen when n=1 or 2 and D represents —C(═O)—, or B represents CH when n=0 and D represents —CH2O— or when n=1 and D represents —O—, R2 represents a hydrogen, a methyl, a fluorine or chlorine atom or a methoxy, HetAr represents a pyridyl or quinolyl group, possibly substituted by a group such as a linear or branched C1-C4 alkyl, a linear or branched C1-C4 alkoxy, a halogen, or a trifluoromethyl, and to their pharmaceutically acceptable salts.

DERIVATIVES OF HETEROARYLSULFONAMIDES, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPY

The present invention concerns derivatives of heteroarylsulfonamides, notably as blockers of Kv potassium channels, and more particularly of channels Kv1.5, Kv4.3 or Kv11.1, their application in clinical therapy and their preparation methods. These compounds correspond to the following general formula (I): where R1 represents one or more substituents of the phenyl core X such as: hydrogen, halogen, trifluoromethyl, trifluoromethoxy, linear or branched C1-C4 alkyl, or linear or branched C1-C4 alkoxy, A represents oxygen or sulphur, B represents nitrogen when n=1 or 2 and D represents ?C(=O)-, or B represents CH when n=0 and D represents ?CH2O? or when n=1 and D represents ?O?, R2 represents a hydrogen, a methyl, a fluorine or chlorine atom or a methoxy, HetAr represents a pyridyl or quinolyl group, possibly substituted by a group such as a linear or branched C1-C4 alkyl, a linear or branched C1-C4 alkoxy, a halogen, or a trifluoromethyl, and to their pharmaceutically acceptable salts.

An environmentally benign procedure for the synthesis of substituted 2-thiobenzothiazoles, 2-thiobenzoxazoles, 2-thiobenzimidazoles, and 1,3-oxazolopyridine-2-thiols

An improved environmentally benign procedure for the synthesis of substituted 2-thio-benzothia(oxa)zoles, 2-thiobenzimidazoles, and 1,3-oxazolopyridine-2-thiols by cyclization of 2-aminophenols, 2-aminothiophenols, 1,2-phenylenediamines, or 2-amino-3-hydroxypyridines with potassium O-ethyldithiocarbonate in PEG 400 or glycerol under directed microwave irradiation is described. The method can be applied to the synthesis of a variety of derivatives. Springer-Verlag 2011.