22876-22-8

Usage

Uses

Used in Photoinitiation Applications:
2-Mercapto-5-methylbenzoxazole is used as a photoinitiator in the polymerization process, facilitating the curing of materials under ultraviolet light. Its ability to absorb light and generate reactive species makes it an effective catalyst for the polymerization of various monomers.
Used in Stabilization Applications:
In the presence of ultraviolet light, 2-Mercapto-5-methylbenzoxazole serves as a stabilizer, protecting materials from degradation and extending their service life. Its stabilizing properties are particularly valuable in applications where materials are exposed to sunlight or other sources of UV radiation.
Used in Pharmaceutical and Agrochemical Synthesis:
2-Mercapto-5-methylbenzoxazole is utilized as an intermediate in the synthesis of various pharmaceutical and agrochemical products. Its unique chemical structure allows for the development of new compounds with potential therapeutic or pesticidal properties.
Used in Corrosion Inhibition:
MMB has demonstrated potential as a corrosion inhibitor, protecting metal surfaces from oxidation and other forms of corrosion. Its use in this application can extend the life of metal components and reduce maintenance costs in various industries.
Used in Detection of Metal Ions:
2-Mercapto-5-methylbenzoxazole also functions as a fluorescent probe for detecting metal ions. Its ability to emit light upon interaction with certain metal ions makes it a valuable tool in analytical chemistry and environmental monitoring.
Used in Chemical Research:
In the field of chemical research, 2-Mercapto-5-methylbenzoxazole is employed for studying the properties and reactions of benzoxazole derivatives. Its unique structure and reactivity provide insights into the behavior of related compounds and contribute to the development of new materials and applications.

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

Upstream product

• 22876-15-9 5-methylbenzo[d]oxazol-2(3H)-one 
• 140-89-6 potassium ethyl xanthogenate 
• 95-84-1 3-amino-4-hydroxytoluene 
• 75-15-0 carbon disulfide 
• 119-33-5 4-methyl-2-nitrophenol 
• 103-72-0 phenyl isothiocyanate 
• 137-26-8 Thiram 
• 128-04-1 sodium dimethyldithiocarbamate 
• 10531-78-9 5-methyl-1,3-benzoxazole 
• 79558-91-1 N-(2-hydroxy-5-methylphenyl)-N'-phenylthiourea 
• 79558-90-0 N¹-methyl-N²-(2-hydroxy-5-methylphenyl)thiourea 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 3770-60-3 2-chloro-5-methyl-1,3-benzoxazole 
• 445260-71-9 2-[(5-methylbenzo[d]oxazol-2-yl)thio]-N-(9H-fluoren-9-yl)acetamide 
• 1237542-35-6 2-(5-methyl-benzoxazol-2-yl)-sulfanyl-N-[4-(1-methyl-4,5-diphenyl-1H-imidazol-2-yl)phenyl]acetamide 
• 1581289-56-6 C₂₀H₁₇N₃O₂S₂ 
• 1158999-40-6 5-methyl-2-(phenylthio)benzo[d]oxazole 
• 439608-30-7 5-methyl-2-methylsulfanyl-benzooxazole 

Relevant academic research and scientific papers

Synthesis of benzoxazole associated benzothiazine-4-ones and their in vitro and in silico antimicrobial, antioxidant activities

In present study, a series of 3-[(5-methyl-1,3-benzoxazol-2-yl)amino]-2-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones (6a-n) were synthesized and elucidated by elemental, FT-IR, 1H & 13C NMR and LC-MS studies. The in vitro antibacter

A new series of benzoxazole-based SIRT1 modulators for targeted therapy of non-small-cell lung cancer

In an attempt to identify potential anticancer agents for non-small-cell lung cancer (NSCLC) targeting sirtuin 1 (SIRT1), the synthesis of a new series of benzoxazoles (3a – i) was carried out through a facile and versatile synthetic route. The compounds were evaluated for their cytotoxic effects on A549 human lung adenocarcinoma and NIH/3T3 mouse embryonic fibroblast cells using the MTT assay. 2-[(5-Nitro-1H-benzimidazol-2-yl)thio]-N-(2-methylbenzoxazol-5-yl)acetamide (3e) and 2-[(5-chloro-1H-benzimidazol-2-yl)thio]-N-(2-methylbenzoxazol-5-yl)acetamide (3g) were the most potent and selective anticancer agents in this series against the A549 cell line, with IC50 values of 46.66 ± 11.54 and 55.00 ± 5.00 μM, respectively. The flow cytometry-based apoptosis detection assay was performed to determine their effects on apoptosis in A549 cells. Both compounds induced apoptosis in a dose-dependent manner. The effects of compounds 3e and 3g on SIRT1 activity were determined. On the basis of in vitro studies, it was observed that compound 3g caused a significant decrease in SIRT1 levels in a dose-dependent manner, whereas compound 3e increased the SIRT1 levels. According to molecular docking studies, the substantial alteration in the type of action could be attributed to the difference between the interactions of compounds 3e and 3g with the same residues in the active site of SIRT1 (PDB code: 4IG9). On the basis of in silico ADME (absorption, distribution, metabolism, and excretion) studies, these compounds are predicted to possess favorable ADME profiles. According to the in vitro and in silico studies, compounds 3e and 3g, small-molecule SIRT1 modulators, were identified as potential orally bioavailable anticancer agents for the targeted therapy of NSCLC.

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.

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, molecular docking, and anticancer activity of benzoxazole derivatives as VEGFR-2 inhibitors

Novel series of benzoxazoles 4a-f-16 were designed, synthesized, and evaluated for anticancer activity against HepG2, HCT-116, and MCF-7 cells. HCT-116 was the most sensitive cell line to the influence of the new derivatives. In particular, compound 5e was found to be the most potent against HepG2, HCT-116, and MCF-7 with IC50 = 4.13 ± 0.2, 6.93 ± 0.3, and 8.67 ± 0.5 μM, respectively. Compounds 5c, 5f, 6b, 5d, and 6c showed the highest anticancer activities against HepG2 cells with IC50 of 5.93 ± 0.2, 6.58 ± 0.4, 8.10 ± 0.7, 8.75 ± 0.7, and 9.95 ± 0.9 μM, respectively; HCT-116 cells with IC50 of 7.14 ± 0.4, 9.10 ± 0.8, 7.91 ± 0.6, 9.52 ± 0.5, and 12.48 ± 1.1 μM, respectively; and MCF-7 cells with IC50 of 8.93 ± 0.6, 10.11 ± 0.9, 12.31 ± 1.0, 9.95 ± 0.8, and 15.70 ± 1.4 μM, respectively, compared with sorafenib as a reference drug with IC50 of 9.18 ± 0.6, 5.47 ± 0.3, and 7.26 ± 0.3 μM, respectively. The most active compounds 5c-f and 6b,c were further evaluated for their vascular endothelial growth factor receptor-2 (VEGFR-2) inhibition. Compounds 5e and 5c potently inhibited VEGFR-2 at lower IC50 values of 0.07 ± 0.01 and 0.08 ± 0.01 μM, respectively, compared with sorafenib (IC50 = 0.1 ± 0.02 μM). Compound 5f potently inhibited VEGFR-2 at low IC50 value (0.10 ± 0.02 μM) equipotent to sorafenib. Our design was based on the essential pharmacophoric features of the VEGFR-2 inhibitor sorafenib. Molecular docking was performed for all compounds to assess their binding pattern and affinity toward the VEGFR-2 active site.

Benzoxazole/benzothiazole-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations

A novel series of benzoxazole/benzothiazole derivatives 4a–c–11a–e were designed, synthesized, and evaluated for anticancer activity against HepG2, HCT-116, and MCF-7 cells. HCT-116 was the most sensitive cell line to the influence of the new derivatives. In particular, compound 4c was found to be the most potent derivative against HepG2, HCT-116, and MCF-7 cells, with IC50 values = 9.45 ± 0.8, 5.76 ± 0.4, and 7.36 ± 0.5 μM, respectively. Compounds 4b, 9f, and 9c showed the highest anticancer activities against HepG2 cells with IC50 values of 9.97 ± 0.8, 9.99 ± 0.8, and 11.02 ± 1.0 μM, respectively, HCT-116 cells with IC50 values of 6.99 ± 0.5, 7.44 ± 0.4, and 8.15 ± 0.8 μM, respectively, and MCF-7 cells with IC50 values of 7.89 ± 0.7, 8.24 ± 0.7, and 9.32 ± 0.7 μM, respectively, in comparison with sorafenib as reference drug with IC50 values of 9.18 ± 0.6, 5.47 ± 0.3, and 7.26 ± 0.3 μM, respectively. The most active compounds 4a–c, 9b,c,e,f,h, and 11c,e were further evaluated for their VEGFR-2 inhibition. Compounds 4c and 4b potently inhibited VEGFR-2 at IC50 values of 0.12 ± 0.01 and 0.13 ± 0.02 μM, respectively, which are nearly equipotent to the sorafenib IC50 value (0.10 ± 0.02 μM). Furthermore, molecular docking studies were performed for all synthesized compounds to assess their binding pattern and affinity toward the VEGFR-2 active site.

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

A facile and effective C–H functionalization strategy for the synthesis of 2-mercaptobenzothiazoles and 2-mercaptobenzoxazoles is described. 1,3-Propanedithiol was employed to convert benzothiazoles and benzoxazoles to the corresponding heteroarylthiols in the presence of potassium hydroxide and DMSO. This novel protocol is featured by direct C–H mercaptalization of heteroarenes and a simple reaction system.

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

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.