87691-89-2

Usage

Uses

Used in Pharmaceutical Industry:
3-PIPERAZIN-1-YL-1,2-BENZISOXAZOLE is used as a reagent for the preparation of [(azaheterocyclyl)thiazolyl] heteroaryl ketones, which are vanin-1 inhibitors. Vanin-1, also known as pantothenate kinase, is an enzyme involved in the regulation of cellular metabolism and has been implicated in various diseases, including cancer and inflammatory disorders. Inhibiting vanin-1 activity with [(azaheterocyclyl)thiazolyl] heteroaryl ketones may offer therapeutic benefits in these conditions.
Used in Organic Synthesis:
3-PIPERAZIN-1-YL-1,2-BENZISOXAZOLE serves as a valuable intermediate in the synthesis of various heterocyclic compounds. Its unique structure allows for the formation of diverse chemical entities with potential applications in medicinal chemistry, materials science, and other fields. 3-PIPERAZIN-1-YL-1,2-BENZISOXAZOLE's reactivity and functional group compatibility make it a promising candidate for the development of new drugs and functional materials.

InChI:InChI=1/C11H13N3O/c1-2-4-10-9(3-1)11(13-15-10)14-7-5-12-6-8-14/h1-4,12H,5-8H2

Upstream product

• 110-85-0 piperazine 
• 16263-52-8 3-chlorobenzisoxazole 
• 21725-69-9 1,2-benz-4-isooxazolin-3-one 
• 89-73-6 salicylhydroxamic acid 
• 29568-74-9 2-chloro-N-hydroxybenzimidoyl chloride 
• 3717-28-0 2-chloro benzaldehyde oxime 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 865787-00-4 1-(4-benzo[d]isoxazol-3-yl-piperazin-1-yl)-2-(2-nitro-phenyl)-ethanone 
• 865787-03-7 1-(4-benzo[d]isoxazol-3-yl-piperazin-1-yl)-2-(4-methyl-2-nitro-phenyl)-ethanone 
• 676118-20-0 C₁₉H₂₀N₄O₃ 
• 1197356-68-5 (4-(benzo[d]isoxazol-3-yl)piperazin-1-yl)(4-methyl-3-(pyridin-2-ylethynyl)phenyl)methanone 
• 1197357-53-1 3-(4-{[3-(pyridin-2-ylethynyl)-4-(trifluoromethyl)phenyl]carbonyl}piperazin-1-yl)-1,2-benzisoxazole 

Relevant academic research and scientific papers

Seeking potent anti-tubercular agents: Design, synthesis, anti-tubercular activity and docking study of various ((triazoles/indole)-piperazin-1-yl/1,4-diazepan-1-yl)benzo[d]isoxazole derivatives

A series of thirty eight novel 3-(4-((substituted-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl/1,4-diazepan-1-yl)benzo[d]isoxazole and 1-(4-(benzo[d]isoxazol-3-yl)piperazin-1-yl/1,4-diazepan-1-yl)-2-(1H-indol-3-yl)substituted-1-one analogues were synthesised, characterised using various analytical techniques and evaluated for in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain and two 'wild' strains Spec. 210 and Spec. 192. The titled compounds exhibited minimum inhibitory concentration (MIC) ranging from 6.16 to >200 μM. Among the tested compounds, 7i, 7y and 7z exhibited moderate activity (MIC = 24.03-29.19 μM) and 7j exhibited very good anti-tubercular activity (MIC = 6.16 μM). Furthermore, 7i, 7j, 7y and 7z were found to be non-toxic against mouse macrophage cell lines when screened for toxicity. All the synthesised compounds were docked to pantothenate synthetase enzyme site to know deferent binding interactions with the receptor.

Design, synthesis and antimycobacterial activity of various 3-(4-(substitutedsulfonyl)piperazin-1-yl)benzo[ d[isoxazole derivatives

In this communication, we synthesized a series of twenty four novel 3-(4-(substitutedsulfonyl)piperazin-1-yl)benzo[d]isoxazole analogues, characterized using various spectroscopic techniques and evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis (MTB) H37Rv strain. The titled compounds exhibited Minimum inhibitory concentration (MIC) between 3.125 and >50 μg/mL. Among the tested compounds, 5c, 6a, 6j and 6p exhibited moderate activity (MIC Combining double low line 12.5 μg/mL), while 5a and 6i exhibited good activity (MIC Combining double low line 6.25 μg/mL) and 6b (MIC Combining double low line 3.125 μg/mL) exhibited very good anti-tubercular activity. In addition, the analogues 5a, 5c, 6a, 6b, 6i, 6j and 6p were subjected to toxicity studies against mouse macrophage (RAW 264.7) cell lines to analyse the selectivity profile of the newly synthesized compounds and selectivity index of the most active compound was found to be >130 indicating suitability of the compound for further drug development. Structure of 6b was further substantiated through single crystal XRD.

DRUG COMBINATIONS CONTAINING PDE4 INHIBITORS AND NSAIDS

The present invention relates to new drug combinations which contain in addition to one or more PDE4-inhibitors at least one NSAID (=non-steroidal anti-inflammatory drug) (2), processes for preparing them and their use in treating in particular respiratory complaints such as for example COPD, chronic sinusitis and asthma. The invention particularly relates to those drug combinations which, in addition to one or more, preferably one PDE4 inhibitor of general formula 1 wherein X is SO or SO2, but preferably SO, and wherein R3 denotes an optionally substituted, mono- or bicyclic, unsaturated, partly saturated or saturated heterocyclic group or an optionally substituted, mono- or bicyclic heteroaryl and wherein R1 and R2 have the meanings given in claim 1, contain at least one NSAID (2), the preparation thereof and the use thereof for the treatment of respiratory complaints.

OXINDOLE SUBSTITUTED PIPERAZINE DERIVATIVES

The invention relates to compounds of the formula (I), wherein Ar, A, R, R1, R2, R3, R4 and R5 are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

Synthesis and Biological Evaluation of 1-(1,2-Benzisothiazol-3-yl)- and (1,2-Benzisoxazol-3-yl)piperazine Derivatives as Potential Antipsychotic Agents

Members of the series of title compounds were tested for potential antipsychotic activity in relevant receptor binding assays and behavioral screens.Structure-activity relationships within the series are discussed.Compound 24 (BMY 13859-1), a (1,2-benzisothiazol-3-yl)piperazine derivative, was selected for further study because of its potent and selective profile in primary CNS tests.It was active in the Sidman avoidance paradigm and blocked amphetamine-induced stereotyped behavior in dogs for up to 7 h.The compound's lack of typical neuroleptic-like effects in therat catalepsy test and its failure to produce dopamine receptor supersensitivity following chronic administration indicate that it should not cause the movement disorders commonly associated with antipsychotic therapy.Although 24 has potent affinity for dopaminergic binding sites, its even greater affinity for serotonin receptors suggests that a serotonergic component may be relevant to its atypical profile.Compound 24 is currently undergoing clinical evaluation in schizophrenic patients.

Benzisothiazole and benzisoxazole piperazine derivatives

Disubstituted N,N-piperazinyl derivatives are disclosed wherein one substituent is benzisothiazol-3-yl or benzisoxazol-3-yl and the other is alkylene attached to heterocycles such as azaspiro[4.5]decanedione, dialkylglutarimide, thiazolidinedione and spirocyclopentylthiazolidinedione or butyrophenone-like groups. The compounds have psychotropic properties and 8-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspior[4.5]decane-7,9-dione is a typical embodiment having selective antipsychotic activity.