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Usage

Uses

Used in Pharmaceutical Industry:
2-Methylthio Benzoxazole is utilized as a building block for the synthesis of various functional molecules and pharmaceutical drugs. Its structural attributes make it a key component in the development of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Methylthio Benzoxazole is employed as a versatile intermediate, contributing to the creation of a wide array of chemical compounds.
Used as Antifungal and Antimicrobial Agent:
2-Methylthio Benzoxazole is explored for its potential as an antifungal and antimicrobial agent, leveraging its chemical properties to combat infections and microbial growth.
Used in Chemical and Biological Sensing Applications:
Capitalizing on its fluorescence properties, 2-Methylthio Benzoxazole is applied in chemical and biological sensing, where it aids in the detection and measurement of various substances in complex environments.

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

Upstream product

• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 
• 77-78-1 dimethyl sulfate 
• 7471-86-5 methyl benzimidate 
• 95-55-6 2-amino-phenol 
• 2382-96-9 2-sulfanyl-1,3-benzoxazole 
• 74-88-4 methyl iodide 
• 54648-79-2 N,N’-diisopropyl-O-methylisourea 
• 273-53-0 benzoxazole 
• 14236-72-7 2-methylsulfanyl-1-phenyl-propan-1-one 
• 616-38-6 carbonic acid dimethyl ester 
• 271-95-4 1,2-benzisoxazole 
• 80-48-8 methyl p-toluene sulfonate 
• 333-27-7 methyl trifluoromethanesulfonate 
• 108805-12-5 3'-(Dimethylamino)spiroazirin> 

Downstream Products

• 68006-75-7 (3-ethyl-benzothiazol-2-yl)-(3-ethyl-benzoxazol-2-yl)-methinium ; iodide 
• 94109-77-0 3-ethyl-5-[5,5-dimethyl-3-(3-methyl-3H-benzoxazol-2-ylidenemethyl)-cyclohex-2-enylidene]-2-thioxo-thiazolidin-4-one 
• 92148-95-3 N-(4-methoxyphenyl)-1,3-benzoxazol-2-amine 
• 26946-72-5 N-(4-nitrophenyl)-1,3-benzoxazol-2-amine 
• 13673-63-7 3-methylbenzoxazole-2-thione 
• 54836-33-8 2-hydrazino-3-methyl-benzooxazolium; toluene-4-sulfonate 
• 4410-25-7 2-(N-phenyl-hydrazino)-benzooxazole 
• 59-49-4 2-Benzoxazolinone 
• 15062-88-1 2-hydrazino-1,3-benzoxazole 
• 4410-22-4 4-nitro-benzaldehyde benzooxazol-2-yl-phenyl-hydrazone 
• 4410-26-8 2-[N-phenyl-N'-(2,4,6-trinitro-phenyl)-hydrazino]-benzooxazole 
• 838-34-6 2-(p-methoxyphenyl)benzoxazole 

Relevant academic research and scientific papers

SH-methylation of SH-containing heterocycles with dimethyl carbonate via phase-transfer catalytic reaction

A reaction of SH-containing heterocycles with dimethyl carbonate (DMC) in the presence of K2CO3 and tetrabutylammonium bromide (Bu4NBr) gave heteroaryl methyl thioethers in 44-93% yields. The reaction was carried out under mild conditions. This method provided a useful synthetic method for preparation of various heteroaryl methyl thioethers without the use of toxic methylic halides or dimethyl sulfate.

RNA-targeting low-molecular-weight fluorophores for nucleoli staining: synthesis,in silicomodelling and cellular imaging

Herein we present our work on the synthesis, investigation of the photophysical properties, interactions with nucleic acids, molecular docking, and imaging application of three carbocyanine dyes. The described low-molecular-weight compounds were found to exhibit high resistance against photobleaching and showed promising optical properties as fluorescent labeling agents for ribonucleic acids. They form strong biocomplexes (log?Ks= 6.11-7.84) and revealed remarkable sensitivity towards RNA, reaching up to a 379 times increase of the emission signal when bound to AU-rich sequences. According to the score values obtained from the molecular docking studies, the compounds show strong binding affinity towards RNA macromolecules. All fluorophores exhibit significant cell tolerance since they were found to be 16 to 60 times less toxic against MRC5 cells (healthy human fibroblasts) compared to the conventional Thiazole Orange - TO. The IC50 concentrations for the compounds were calculated up to 40 μM in human fibroblasts MRC5, A549 adenocarcinomic human alveolar basal epithelial cells, the HCT116 human colon cancer cell line, and MDA-MB-231 adenocarcinoma cells. Analyzing the dyes for preferential cytotoxicity towards cancer cell lines in comparison to the normal human fibroblasts, we found a candidate exhibiting promising anticancer potential. Based on the selectivity (Si) towards cancer cells and more specifically against difficult to treat colon HCT116 carcinoma, we can suggest these small molecules as an interesting platform for further development. We have also demonstrated the efficiency of the carbocyanines as staining agents forin vivolabeling of human cells as well as microbial and eukaryotic cells.

New cyanine dyes as base surrogates in PNA: Forced intercalation probes (FIT-probes) for homogeneous SNP detection

Forced intercalation probes (FIT-probes) are nucleic acid probes, in which an intercalator cyanine dye such as thiazole orange (TO) serves as a replacement of a canonical nucleobase. These probes signal hybridization by showing strong increases of fluorescence. TO in FIT-probes responds to adjacent base mismatches by attenuation of fluorescence intensities at conditions where both matched and mismatched target DNA are bound. The interesting features of TO labeled FIT-probes posed the question whether the forced intercalation concept can be extended to other cyanine dyes of the thiazole orange family. Herein, we present the synthesis of three asymmetrical cyanine dyes and their incorporation into PNA-conjugates by means of both divergent and linear solid-phase synthesis. Melting analysis revealed that the DNA affinity of PNA probes remained high irrespective of the replacement of a nucleobase by the cyanines YO (oxazole yellow), MO or JO. Of the three new tested dye-PNA-conjugates, the YO-containing PNA has properties useful for homogeneous SNP detection. YO-PNA is demonstrated to signal the presence of fully complementary DNA by up to 20-fold enhancement of fluorescence. In addition, YO emission discriminates against single base mismatches by attenuation of fluorescence. Oxazole yellow (YO) as a base surrogate in PNA may prove useful in the multiplex detection of single base mutations at non-stringent conditions.

Tunable Amine-Reactive Electrophiles for Selective Profiling of Lysine

Proteome profiling by activated esters identified >9000 ligandable lysines but they are limited as covalent inhibitors due to poor hydrolytic stability. Here we report our efforts to design and discover a new series of tunable amine-reactive electrophiles (TAREs) for selective and robust labeling of lysine. The major challenges in developing selective probes for lysine are the high nucleophilicity of cysteines and poor hydrolytic stability. Our work circumvents these challenges by a unique design of the TAREs that form stable adducts with lysine and on reaction with cysteine generate another reactive electrophiles for lysine. We highlight that TAREs exhibit substantially high hydrolytic stability as compared to the activated esters and are non-cytotoxic thus have the potential to act as covalent ligands. We applied these alternative TAREs for the intracellular labeling of proteins in different cell lines, and for the selective identification of lysines in the human proteome on a global scale.

HMOX1 inducers

The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.

Microwave-Enhanced On-Water Amination of 2-Mercaptobenzoxazoles to Prepare 2-Aminobenzoxazoles

In this work, we developed a catalyst-free amination of 2-mercaptobenzoxazoles on water under microwave irradiation. The product, 2-aminobenzoxazoles, was successfully produced via direct amination with various amines in moderate to high yields. The formal synthesis of Suvorexant, a medication for the treatment of insomnia, was accomplished using a developed amination process. The reaction was completed in an hour at 100-150 °C in a microwave reactor without the use of external catalyst or additive. Key benefits of this process include an on-water reaction, short reaction time, being scalable and catalyst-free, and use of 2-mercaptobenzoxazoles as an inexpensive starting material having low environmental impact in its preparation.

5HT1F RECEPTOR AGONISTS AND MITOCHONDRIAL BIOGENESIS

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, promote mitochondrial biogenesis and are useful for the treatment of, for example, acute kidney injury and chronic kidney disease.

An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor

A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented. Water is used as the source of oxygen to enable the oxidation process. The oxidation reaction utilizes the same reagents in all scenarios and the selectivity is solely governed by the applied potential. The procedure exhibits a broad scope and good functional group compatibility providing access to various sulfoxides (15 examples), sulfones (15 examples) and disulfides (6 examples). The use of continuous flow allows the optimal reaction parameters (e.g. residence time, applied voltage) to be rapidly assessed, to avoid mass- and heat-transfer limitations and to scale the electrochemistry.

A novel synthesis of 2-alkylthiobenzothiazoles and 2-alkylthiobenzoxazoles

3H-Benzothiazole-2-thione and 3H-benzoxazole-2-thione were selectively S-alkylated by use of O-alkylisoureas as the alkylating reagents. The reactions could be performed under mild reaction conditions in short reaction times, and high yields were obtained using O-primary-alkylisoureas, whereas low yields were obtained with sec-and tert-alkylisoureas.

Pd- and Ni-catalyzed cross-coupling reactions of functionalized organozinc reagents with unsaturated thioethers

A variety of unsaturated thioethers have been subjected to cross-coupling reactions with functionalized zinc reagents in the presence of a transition-metal catalyst. Three different catalytic systems based on Pd(OAc)2 or [Ni(acac)2] and the ligands S-Phos or DPE-Phos gave the best results. N-Heterocyclic thioethers based on a pyridine, pyrimidine, pyrazine, pyridazine, triazine, benzothiazole, benzoxazole, pyrrole, or quinazoline ring, as well as thiomethylacetylenes, serve as electrophiles in this cross-coupling reaction. Aryl-, heteroaryl-, benzylic, and alkylzinc halides with sensitive functionalities, such as ester, nitrile, or ketone groups react at ambient temperature with unsaturated thioethers using a Ni catalyst. The corresponding Pd-catalyzed reactions require slightly higher temperatures. Large-scale cross-coupling experiments (10-20 mmol) with N-heterocycles are also reported.