22876-19-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Chlorobenzooxazole-2-thiol is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique chemical structure allows it to be a crucial component in the synthesis of complex molecules with potential therapeutic applications.
Used in Synthesis of 5-chloro-2-(4-methyl-1-piperazinyl)benzoxazole:
5-Chlorobenzooxazole-2-thiol is used as a key building block in the synthesis of 5-chloro-2-(4-methyl-1-piperazinyl)benzoxazole, a compound with potential applications in the development of new drugs and pharmaceuticals.
Used in Synthesis of 5-chloro-2-morpholin-4-yl-1,3-benzoxazole:
Additionally, 5-Chlorobenzooxazole-2-thiol is utilized in the synthesis of 5-chloro-2-morpholin-4-yl-1,3-benzoxazole, another compound that may have significance in the pharmaceutical industry due to its potential therapeutic properties.

InChI:InChI=1/C7H4ClNOS/c8-4-1-2-6-5(3-4)9-7(11)10-6/h1-3H,(H,9,11)

Upstream product

• 463-71-8 thiophosgene 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 75-15-0 carbon disulfide 
• 140-89-6 potassium ethyl xanthogenate 
• 103-72-0 phenyl isothiocyanate 
• 108-43-0 3-monochlorophenol 
• 17200-29-2 5-chloro-benzoxazole 
• 137-26-8 Thiram 
• 89-64-5 p-chloro-o-nitrophenol 
• 21524-25-4 2-hydroxy-5-chloroazobenzene 
• 106-48-9 4-chloro-phenol 
• 95-25-0 5-chloro-2-benzoxazolinone 

Downstream Products

• 79558-94-4 5-chloro-N-phenyl-1,3-benzoxazole-2-amine 
• 3621-81-6 2,5-dichloro-1,3-benzoxazole 
• 538-74-9 dibenzyl sulfide 
• 31080-68-9 5-chloro-2-methoxybenzoxazole 
• 87054-08-8 C₉H₁₀ClNO₃ 
• 87054-14-6 2-bibenzyloxy-5-chlorobenzoxazole 
• 78720-45-3 1-(5-Chloro-2-hydroxy-phenyl)-3-propyl-thiourea 
• 87054-07-7 2-isopropylthio-5-chlorobenzoxazole 
• 96292-91-0 5-chloro-3-isochroman-1-ylbenzoxazoline-2-thione 
• 87054-09-9 C₁₁H₁₄ClNO₃ 
• 87054-13-5 2-(tert-butylthio)-5-chlorobenzoxazole 
• 78720-47-5 1-(5-Chloro-2-hydroxy-phenyl)-3-cyclohexyl-thiourea 
• 87054-12-4 2-(benzylthio)-5-chlorobenzo[d]oxazole 
• 78720-44-2 1-(5-Chloro-2-hydroxy-phenyl)-3-ethyl-thiourea 

Relevant academic research and scientific papers

Antimalarial benzoheterocyclic 4-aminoquinolines: Structure-activity relationship, in vivo evaluation, mechanistic and bioactivation studies

A novel class of benzoheterocyclic analogues of amodiaquine designed to avoid toxic reactive metabolite formation was synthesized and evaluated for antiplasmodial activity against K1 (multidrug resistant) and NF54 (sensitive) strains of the malaria parasite Plasmodium falciparum. Structure-activity relationship studies led to the identification of highly promising analogues, the most potent of which had IC50s in the nanomolar range against both strains. The compounds further demonstrated good in vitro microsomal metabolic stability while those subjected to in vivo pharmacokinetic studies had desirable pharmacokinetic profiles. In vivo antimalarial efficacy in Plasmodium berghei infected mice was evaluated for four compounds, all of which showed good activity following oral administration. In particular, compound 19 completely cured treated mice at a low multiple dose of 4 × 10 mg/kg. Mechanistic and bioactivation studies suggest hemozoin formation inhibition and a low likelihood of forming quinone-imine reactive metabolites, respectively.

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.

Green synthesis of therapeutically active 1,3,4-oxadiazoles as antioxidants, selective COX-2 inhibitors and their in silico studies

A modest, competent and green synthetic procedure for novel coumarinyl-1,3,4-oxadiazolyl-2-mercaptobenzoxazoles 8i-t has been reported. Analysis of the docked (PDB ID: 5IKR; A-Chain) poses of the compounds illustrated that they adopt identical conformations to the extremely selective COX-2 inhibitor. The biological outcomes as well as computational study suggested that the compounds originated to have elevated resemblance towards COX-2 enzyme than COX-1. The compounds 8i, 8l, 8q, 8r, 8s and 8t emerged as most potent and selective COX-2 inhibitors in contrast with Mefenamic acid. The selectivity index of 8l, 8n and 8r was respectively found to be 33.95, 20.25 and 24.98 which manifested their high selectivity against COX-2. Interestingly, the compounds which were active as COX-2 inhibitors were also active as antioxidant agents.

Microwave facilitated one-pot three component synthesis of coumarin-benzoxazole clubbed 1,2,3-triazoles: Antimicrobial evaluation, molecular docking and in silico ADME studies

4-((4-((Benzo[d]oxazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2H-chromen-2-ones 7k–z were synthesized by conventional as well as microwave irradiation method in order to obtain antimicrobial agents. The present green synthetic protocol explores facile work up procedure with excellent yields (82–92%) and purity. Docking studies exhibited strong binding interactions with enzyme N-myristoyl transferase (PDB ID: 4CAW) with excellent C-score values. Compounds 7k–z were screened for their in vitro antimicrobial activities. The compounds 7w and 7 y exhibited excellent antimicrobial results for all the tested microorganisms at MICs ranging from 3.12 to 6.25 μg/ml in comparison with the marketed drugs.

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.

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.

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.

Preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as mercapto source

The invention belongs to the synthesis field of medicine chemical intermediate, and provides a preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as a mercapto source. According to the preparation method, under inert gas protection, in dimethyl sulphoxide solvent, substituted benzoxazole(thiazole) and 1,3-dimercaptopropane are subjected to 120 to 140 DEG Cheating stirring in the presence of an alkali, after 12 to 24h of reaction, an obtained reaction solution is cooled to room temperature, and is subjected to acidifying post-treatment so as to obtaina product. The reaction conditions are simple; function group compatibility is excellent; yield is relatively high; the obtained 2-mercaptobenzoxazole(thiazole) compounds are important organic synthesis intermediates; application range in the field of chemical raw material, pesticide, and medicine is wide; and practical value and social and economic benefit are excellent.

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.

A [2 - [(5 - chloro - benzo oxazole - 2 - yl) (3 - oxo-butyl) amino] ethyl] carbamic acid tert-butyl preparation method (by machine translation)

The invention discloses a [2 - [(5 - chloro - benzo oxazole - 2 - yl) (3 - oxo-butyl) amino] ethyl] carbamic acid tert-butyl preparation method, in order to ethylenediamine, vinyl, 2 - amino - 4 - chlorophenol and the like as raw materials, after five-step reaction to obtain the target product [2 - [(5 - chloro - benzo oxazole - 2 - yl) (3 - oxo-butyl) amino] ethyl] tert-butyl carbamate. The invention has simple operation, environment friendly, comprehensive yield is 52% more, than the existing 35.6% yield, with a remarkable enhancement, greatly reduces the production cost of the existing drugs, is suitable for industrial scale production. (by machine translation)