Category: Benzisoxazole

Synthesis, evaluation of analgesic and anti-inflammatory activities of substituted 1,2-benzoxazolone and 3-chloro-1,2-benzoxazole derivatives was written by Kiran, B. Ravi;Vijayakumar, G. R.;Bharath, H. S.;Sivakumar, R.;Sindhu, S.;Prakash, M. Shet. And the article was included in International Journal of Pharmaceutical Sciences and Research in 2015.Quality Control of 3-Chloro-6-methylbenzo[d]isoxazole The following contents are mentioned in the article:

Herein method for the synthesis of substituted 1,2-benzoxazolone I [R¹ = H, NO₂, Br; R² = H, Me, F; R³ = H, NO₂, F] and 3-chloro-1,2-benzoxazole derivatives II [R¹ = H, NO₂, Br; R² = H, Me, F; R³ = H, NO₂, F] was described. A new scheme was adapted for the construction of 1,2-benzoxazole ring from salicylic acid and its derivatives which leads to the formation of series of methyl-2-hydroxy-5-bromo benzoate, Me 2-hydroxybenzoates and N,2-dihydroxybenzamides substituted title compounds Synthesized compounds were characterized by IR, ¹H-NMR and Mass spectral anal. Spectral data confirmed the compounds formation. Final compounds I and II were screened for their in-vivo analgesic activity by acetic acid induced writhing method in rats and anti-inflammatory activity by carrageenan-induced paw edema model. Among the compounds screened compound I [R¹, R², R³ = H] and compound II [R¹, R² = H; R³ = NO₂] showed good analgesic activity of about 45% (writhing mean 8.9) and 54% (writhing mean 7.5) inhibition resp. at 5 mg/Kg po dosage. Compounds I [R¹ = NO₂; R², R³ = H] and II [R¹ = NO₂; R², R³ = H] (both having inhibition edema of 66.1%) showed significant anti-inflammatory activity. Other derivatives exhibited moderate to good analgesic and anti-inflammatory activities. This study involved multiple reactions and reactants, such as 3-Chloro-6-methylbenzo[d]isoxazole (cas: 16302-64-0Quality Control of 3-Chloro-6-methylbenzo[d]isoxazole).

3-Chloro-6-methylbenzo[d]isoxazole (cas: 16302-64-0) belongs to benzisoxazole derivatives. The benzisoxazole analogs represent one of the privileged structures in medicinal chemistry and there has been an increasing number of studies on benzisoxazole-containing compounds. Benzisoxazoles are found to display a variety of biological activities such as antiinflammatory, antioxidant, antidepressant, hypertensive, anticonvulsant, and anticoagulant properties.Quality Control of 3-Chloro-6-methylbenzo[d]isoxazole

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Benzimidazolones: A New Class of Selective Peroxisome Proliferator-Activated Receptor γ (PPARγ) Modulators was written by Wang, Chualin;McCann, Margaret E.;Doebber, Thomas W.;Wu, Margaret;Chang, Ching H.;McNamara, Lesley;McKeever, Brian;Mosley, Ralph T.;Berger, Joel P.;Meinke, Peter T.. And the article was included in Journal of Medicinal Chemistry in 2011.Formula: C8H6ClNO The following contents are mentioned in the article:

A series of benzimidazolone carboxylic acids and oxazolidinediones were designed and synthesized in search of selective PPARγ modulators (SPPARγMs) as potential therapeutic agents for the treatment of type II diabetes mellitus (T2DM) with improved safety profiles relative to rosiglitazone and pioglitazone, the currently marketed PPARγ full agonist drugs. Structure-activity relationships of these potent and highly selective SPPARγMs were studied with a focus on their unique profiles as partial agonists or modulators. A variety of methods, such as X-ray crystallog. anal., PPARγ transactivation coactivator profiling, gene expression profiling, and mutagenesis studies, were employed to reveal the differential interactions of these new analogs with PPARγ receptor in comparison to full agonists. In rodent models of T2DM, benzimidazolone analogs such as (5R)-5-(3-{[3-(5-methoxybenzisoxazol-3-yl)benzimidazol-1-yl]methyl}phenyl)-5-methyloxazolidinedione I demonstrated efficacy equivalent to that of rosiglitazone. Side effects, such as fluid retention and heart weight gain associated with PPARγ full agonists, were diminished with I in comparison to rosiglitazone based on studies in two independent animal models. This study involved multiple reactions and reactants, such as 3-Chloro-6-methylbenzo[d]isoxazole (cas: 16302-64-0Formula: C8H6ClNO).

3-Chloro-6-methylbenzo[d]isoxazole (cas: 16302-64-0) belongs to benzisoxazole derivatives. The benzisoxazole analogs represent one of the privileged structures in medicinal chemistry and there has been an increasing number of studies on benzisoxazole-containing compounds. The 1,2-benzisoxazole ring containing drugs zonisamide and risperidone have been used as anticonvulsants.Formula: C8H6ClNO

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Microwave-promoted synthesis of 3-amino-substituted 1,2-benzisoxazole derivatives was written by Smith, Jessica A.;Le, Giang;Jones, Eric D.;Deadman, John. And the article was included in Future Medicinal Chemistry in 2010.Electric Literature of C8H6ClNO The following contents are mentioned in the article:

1,2-Benzisoxazole derivatives have been the focus of numerous studies due to their biol. and chem. interest. The title compounds [i.e., 1,2-benzisoxazole-3-amine derivatives] were obtained by a microwave-promoted nucleophilic aromatic substitution of 3-chloro-6-methyl-1,2-benzisoxazole and 3-chloro-7-methyl-1,2-benzisoxazole with amines (54-90% yield). The above-mentioned targets included 3-(4-morpholinyl)-1,2-benzisoxazole, N-alkyl-1,2-benzisoxazol-3-amine, etc., and the product structures were confirmed by ESI, IR, NMR. The 3-chloro-1,2-benzisoxazole derivatives were also prepared by heating with microwave irradiation in quant. yields in 2 h, from the corresponding 3-hydroxy-1,2-benzisoxazole derivatives . This efficient microwave-assisted pathway could be applied to a variety of substrates in the further development of substituted 1,2-benzisoxazole derivatives This study involved multiple reactions and reactants, such as 3-Chloro-6-methylbenzo[d]isoxazole (cas: 16302-64-0Electric Literature of C8H6ClNO).

3-Chloro-6-methylbenzo[d]isoxazole (cas: 16302-64-0) belongs to benzisoxazole derivatives. Benzisoxazoles are currently the most important building blocks in drug discovery, with a high number of positive hits encountered in biological screens of this heterocycle and its derivatives. These include antidepressants, anti-inflammatory agents, antimalarial drugs, antipsychotics, antiviral agents, steroids, and anesthetics.Electric Literature of C8H6ClNO

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

3-Chloro-1,2-benzisoxazoles was written by Boeshagen, Horst. And the article was included in Chemische Berichte in 1967.Recommanded Product: 3-Chloro-6-methylbenzo[d]isoxazole The following contents are mentioned in the article:

3-Hydroxy-1,2-benzisoxazole (I) treated with POCl3 gave 3-chloro-1,2-benzisoxazole. The Cl atom was moderately reactive, showing some nucleophilic exchange reactions. This study involved multiple reactions and reactants, such as 3-Chloro-6-methylbenzo[d]isoxazole (cas: 16302-64-0Recommanded Product: 3-Chloro-6-methylbenzo[d]isoxazole).

3-Chloro-6-methylbenzo[d]isoxazole (cas: 16302-64-0) belongs to benzisoxazole derivatives. Benzisoxazoles are currently the most important building blocks in drug discovery, with a high number of positive hits encountered in biological screens of this heterocycle and its derivatives. The unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on. Recommanded Product: 3-Chloro-6-methylbenzo[d]isoxazole

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

On November 22, 2001, Yamada, Akira; Spears, Glen; Hayashida, Hisashi; Tomishima, Masaki; Ito, Kiyotaka; Imanishi, Masashi published a patent.Reference of 3-Chloro-6-fluorobenzo[d]isoxazole The title of the patent was Preparation of N-imidazolylphenyl-5,6-dihydrobenzo[h]quinazolin-4-amines and other N-containing heterocyclic amines as 5-hydroxytryptamine antagonists for treatment of CNS disorders. And the patent contained the following:

Title compounds AMQNHZ [I; wherein A = H, (un)substituted, unsaturated, N-containing heterocyclic group, or C(NH)NHR; R = (un)substituted aryl or heterocyclic group; M = (CH2)n, (CH2)nO(CH2)m, or (CH2)nNH(CH2)m; n and m = independently 0-2; Q = (un)substituted cycloalkylene group, arylene, or divalent heterocyclic group; Z = (un)substituted, unsaturated, mono-, di-, tri-, or tetra-cyclic, N-containing heterocyclic group which may contain addnl. N, O, and S atoms as the ring member(s), e.g. indeno[1,2,3-de]phthalazinyl or 5,6-dihydrobenzo[h]quinazolinyl; and the prodrugs or pharmaceutically acceptable salts thereof] were prepared For example, a mixture of 4-chloro-5,6-dihydrobenzo[h]quinazoline, 3-(1,2-dimethyl-1H-imidazol-5-yl)aniline, and 1,3-dimethyl-2-imidazolidinone was heated for an hour at 200°C, cooled, treated with 1N aqueous NaOH and water, and worked up to give II. I are 5-hydroxytryptamine (5-HT) antagonists useful for the prevention and/or treatment of central nervous system (CNS) disorders, such as anxiety, depression, obsessive compulsive disorders, migraine, anorexia, Alzheimer’s disease, sleep disorders, bulimia, panic attacks, withdrawal from drug abuse, schizophrenia, and disorders associated with spinal trauma and/or head injury (no data). The experimental process involved the reaction of 3-Chloro-6-fluorobenzo[d]isoxazole(cas: 374554-89-9).Reference of 3-Chloro-6-fluorobenzo[d]isoxazole

The Article related to imidazolylphenyl benzoquinazolinamine preparation hydroxytryptamine antagonist, benzoquinazolinamine imidazolylphenyl preparation central nervous system disorder treatment and other aspects.Reference of 3-Chloro-6-fluorobenzo[d]isoxazole

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

On June 28, 2012, Boss, Christoph; Brotschi, Christine; Heidmann, Bibia; Sifferlen, Thierry; Williams, Jodi T. published a patent.Computed Properties of 374554-89-9 The title of the patent was 3,8-Diazabicyclo[4.2.0]octane derivatives as orexin receptor antagonists and their preparation and use for the treatment of diseases. And the patent contained the following:

The invention relates to 3,8-Diazabicyclo[4.2.0]octane derivatives of formula cis-I, which are orexin receptor antagonists and which are useful in the treatment of diseases. Compounds of formula cis-I wherein Ar1is substituted Ph and substituted 5- to 6-membered heteroaryl; Ar2 is substituted 5- to 6-membered heteroaryl and substituted 8- to 10-membered bicyclic heteroaryl; and pharmaceutically acceptable salts thereof, are claimed. Example compound cis-II was prepared by multistep procedure (procedure given). All the invention compounds were evaluated for their orexin receptor antagonistic activity. From the assay, it was determined that compound cis-II exhibited IC50 values of 1 nM and 5 nM towards OX1 and OX2, resp. The experimental process involved the reaction of 3-Chloro-6-fluorobenzo[d]isoxazole(cas: 374554-89-9).Computed Properties of 374554-89-9

The Article related to diazabicyclooctane preparation orexin receptor antagonist treatment disease, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Computed Properties of 374554-89-9

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

On August 13, 2020, Genung, Nathan; Guckian, Kevin M.; Vessels, Jeffrey; Zhang, Lei; Gianatassio, Ryan; Lin, Edward Yin Shiang; Xin, Zhili published a patent.Quality Control of 3-Chloro-6-fluorobenzo[d]isoxazole The title of the patent was Preparation of heteroaryloxypyrrolidinylmethylthiazolylacetamide derivatives and analogs for use as O-GlcNAcase inhibitors. And the patent contained the following:

Title compounds I [R1 = halo, alkyl, haloalkyl, or alkoxy; R3 = H or alkyl; R4 = H, alkyl, haloalkyl, or cycloalkyl; or R3 and R4 are taken together with their intervening atoms to form an (un)substituted heterocyclyl; R5 = (un)substituted bicyclic aryl, bicyclic heteroaryl, bicyclic cycloaliphatic, or bicyclic heterocyclyl; each Y independently = CH, C(halo), N, etc. wherein at least one is N; Z = C(O), CH2C(O), (CH2)2, etc.; n = 0 to 8; p = 0 or 1; with provisions], and their pharmaceutically acceptable salts, are prepared and disclosed as O-glycoprotein-2-acetamido-2-deoxy-3-D-glucopyranosidase (O-GlcNAcase) inhibitors. Thus, e.g., II was prepared by a multistep procedure (preparation given). I were evaluated in OGA enzyme inhibition biochem. assays, e.g., II demonstrated an IC50 value of <1.0 nM. The experimental process involved the reaction of 3-Chloro-6-fluorobenzo[d]isoxazole(cas: 374554-89-9).Quality Control of 3-Chloro-6-fluorobenzo[d]isoxazole

The Article related to thiazolylacetamide heteroaryloxypyrrolidinylmethyl preparation oglcnacase oga inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Thiazoles, Isothiazoles and other aspects.Quality Control of 3-Chloro-6-fluorobenzo[d]isoxazole

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics