October 2022 | Page 3 of 7 | Heterocyclic Building Blocks-Benzisoxazole

Kopf, Sara’s team published research in European Journal of Organic Chemistry in 2022-05-19 | 84163-77-9

European Journal of Organic Chemistry published new progress about Deuteration, regioselective. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Computed Properties of 84163-77-9.

Kopf, Sara; Liu, Jiali; Franke, Robert; Jiao, Haijun; Neumann, Helfried; Beller, Matthias published the artcile< Base-Mediated Remote Deuteration of N-Heteroarenes - Broad Scope and Mechanism>, Computed Properties of 84163-77-9, the main research area is heteroarene deuterated dimethyl sulfoxide regioselective deuteration; deuterated heteroarene preparation.

Using KOtBu as base and DMSO-d6 as deuterium source, a general and applicable method was presented for the selective deuteration of a set of nitrogen-containing heterocycles (pyridines, azines and bioactive mols.). Exptl. and DFT mechanistic studies indicated that this reaction proceeded via deprotonation of the substrates by the dimsyl anion. The relative thermodn. stability of the heterocycle anions determines the distribution and degree of deuteration.

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

Shah, Urjita H’s team published research in ACS Chemical Neuroscience in 2019-05-15 | 84163-77-9

ACS Chemical Neuroscience published new progress about 5-HT2A antagonists. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

Shah, Urjita H.; Gaitonde, Supriya A.; Moreno, Jose L.; Glennon, Richard A.; Dukat, Malgorzata; Gonzalez-Maeso, Javier published the artcile< Revised Pharmacophore Model for 5-HT2A Receptor Antagonists Derived from the Atypical Antipsychotic Agent Risperidone>, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is antipsychotics schizophrenia HT2A receptor antagonist risperidone pharmacophore model; Antipsychotics; pharmacophore; risperidone; schizophrenia; serotonin 5-HT2A receptor.

Pharmacophore models for 5-HT2A receptor antagonists consist of two aromatic/hydrophobic regions at a given distance from a basic amine. We have previously shown that both aromatic/hydrophobic moieties are unnecessary for binding or antagonist action. Here, we deconstructed the 5-HT2A receptor antagonist/serotonin-dopamine antipsychotic agent risperidone into smaller structural segments that were tested for 5-HT2A receptor affinity and function. We show, again, that the entire risperidone structure is unnecessary for retention of affinity or antagonist action. Replacement of the 6-fluoro-3-(4-piperidinyl)-1,2-benz[d]isoxazole moiety by isosteric tryptamines resulted in retention of affinity and antagonist action. Addnl., 3-(4-piperidinyl)-1,2-benz[d]isoxazole (10), which represents less than half the structural features of risperidone, retains both affinity and antagonist actions. 5-HT2A receptor homol. modeling/docking studies suggest that 10 binds in a manner similar to risperidone and that there is a large cavity to accept various N4-substituted analogs of 10 such as risperidone and related agents. Alterations of this “”extended”” moiety improve receptor binding and functional potency. We propose a new risperidone-based pharmacophore for 5-HT2A receptor antagonist action.

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

Byrappa, Sathish’s team published research in Anti-Cancer Agents in Medicinal Chemistry in 2019-04-30 | 84163-77-9

Anti-Cancer Agents in Medicinal Chemistry published new progress about Angiogenesis. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Reference of 84163-77-9.

Byrappa, Sathish; Rachaiah, Kavitha; Kotian, Sumana Y.; Balaraju, Yashaswini; Prabhuswamimath, Samudyata C.; Rai, Kuriya M. L.; Salimath, Bharathi P. published the artcile< Synthesis and Screening of Pro-apoptotic and Angio-inhibitory Activity of Novel Benzisoxazole Derivatives both In Vitro and In Vivo>, Reference of 84163-77-9, the main research area is phenyl dihydroisoxazolyl methylpiperidinyl fluorobenzoisoxazole preparation; antitumor antiangiogenic activity retinal neovascularization apoptosis; Benzisoxazole; anti-angiogenesis; anti-cancer; antiproliferative; apoptosis; breast cancer; cytotoxicity; piperidine..

Novel derivatives of Benzisoxazoles I [R1 = H, MeO, BnO; R2 = H, F, MeO, Cl, BnO; R3 = H, MeO] were synthesized and screened for their biol. potential. Chem. synthesis, Mass spectrometry (HRMS), cell proliferation and cytotoxicity assay, wound healing assay, flow cytometry and nuclear staining were reported. Angio-inhibitory activity assessed by corneal micropocket assay and in-vivo peritoneal angiogenesis assay. Compounds I were synthesized and screened for their biol. potency by both in-vitro and in-vivo exptl. models. Among the series, compound I [R1 = BnO, R2 = MeO, R3 = H] was found to be most promising, with an average IC50 value of 50.36 ± 1.7 μM in MTT assay and showed 81.3% cell death. The compound I [R1 = BnO, R2 = MeO, R3 = H] also showed 60-70% inhibition on a recombinant Metastasis-Associated protein (MTA1) induced proliferation and cell migration in MDAMB-231 cells, which is known to play a major role in angiogenesis. The anti-tumor studies inferred the regression of tumor activity. This was due to inhibition of neovascularization and evoking apoptosis process as assessed by corneal vascularization, peritoneal angiogenesis and apoptotic hallmarks in compound I [R1 = BnO, R2 = MeO, R3 = H] treated cells. These findings not only showed the biol. efficacy of compound I [R1 = BnO, R2 = MeO, R3 = H] but it was also an effective beginning to explore the mechanism of metastasis and cancer therapy strategy targeting MTA1. The observed biol. activity made compound I [R1 = BnO, R2 = MeO, R3 = H] an attractive drug candidate.

Anti-Cancer Agents in Medicinal Chemistry published new progress about Angiogenesis. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Reference of 84163-77-9.

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

Slawik, T.’s team published research in Acta Chromatographica in 2009 | CAS: 65685-50-9

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.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. Reference of 5-Bromobenzo[d]isoxazol-3(2H)-one The unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.

Slawik, T.; Skibinski, R.; Paw, B.; Dzialo, G. published an article in Acta Chromatographica. The title of the article was 《Reversed-phase TLC study of the lipophilicity of some 3-hydroxy-1,2-Benzisoxazoles substituted in the benzene ring》.Reference of 5-Bromobenzo[d]isoxazol-3(2H)-one The author mentioned the following in the article:

The relative lipophilicity, RM0, and specific hydrophobic surface area of eleven 3-hydroxy-1,2-benzoisoxazoles substituted in the benzene ring (two isomeric fluoro, three isomeric chloro, three isomeric bromo and dibromo derivatives, and a nitro derivative) have been studied by reversed-phase thin layer chromatog. (RP-TLC) on silica gel RP-C18 plates with methanol-water mixtures as mobile phases. Linear correlation between the volume fraction of methanol and RM values a limited range was established with high correlation coefficients (r > 0.99). Lipophilicity RM0 was compared with computed partition coefficients IAlogP, AlogPs, clogP, milogP, logPKOWIN and xlogP. The best correlation (r > 0.9) was found between RM0 and logPKOWIN anx xlogP values. Principal-components anal. (PCA) was also used to compare RM0 values with computed partition coefficients. The chromatog. behavior of 3-hydroxy-1,2-benzisoxazoles was compared with that of their bioisosteric analogs 1,2-benzisothiazolonoles. Exptl. RM0 values for both groups of compounds were in accordance with the equation RM0 = aRM0 + b (r > 0.9). In the experimental materials used by the author, we found 5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9Reference of 5-Bromobenzo[d]isoxazol-3(2H)-one)

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

Smalley, R. K.’s team published research in Science of Synthesis in 2002 | CAS: 65685-50-9

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.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 unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.HPLC of Formula: 65685-50-9

In 2002,Science of Synthesis included an article by Smalley, R. K.. HPLC of Formula: 65685-50-9. The article was titled 《Product class 10: 1,2-benzisoxazoles and related compounds》. The information in the text is summarized as follows:

A review presents various methods of ring-closure reaction and substituent modification for the synthesis of 1,2-benzisoxazoles and related compounds In the experiment, the researchers used 5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9HPLC of Formula: 65685-50-9)

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.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 unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.HPLC of Formula: 65685-50-9

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

Bien, Irena’s team published research in Acta Poloniae Pharmaceutica in 1981 | CAS: 65685-50-9

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.Application of 65685-50-9The 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 unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.

The author of 《2-Alkylaminomethylbenzisoxazolin-3-ones》 were Bien, Irena; Domagalina, Eugenia. And the article was published in Acta Poloniae Pharmaceutica in 1981. Application of 65685-50-9 The author mentioned the following in the article:

3-Hydroxybenzisoxazole and its halo substituted derivatives were converted in the Mannich reaction into 16 new I (R = H, Cl, Br, R1 = H; R = H, R1 = 6-Cl, 6-R; R = Br, R1 = 7-Br; R2 = 4-morpholinyl, 1-piperidinyl, 4-methyl-1-piperazinyl). A similar reaction with piperazine gave 6 II; analogous compounds were obtained from 2,5-dimethylpiperazine. The yields varied from 41-90% for I almost quant. for II. In tests against Trichomonas vaginalis, I (R = Cl, R1 = H, R2 = 4-morpholinyl) revealed activity higher than that of metronidazole and tinidazole; it was also active against Rhabdilis strongyloides. In the experiment, the researchers used 5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9Application of 65685-50-9)

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

Wrubel, Juergen’s team published research in Zeitschrift fuer Chemie in 1980 | CAS: 65685-50-9

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.SDS of cas: 65685-50-9The 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 unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.

Wrubel, Juergen published an article on January 31 ,1980. The article was titled 《2-Substituted 5-amino-1,2-benzisoxazoles》, and you may find the article in Zeitschrift fuer Chemie.SDS of cas: 65685-50-9 The information in the text is summarized as follows:

Nitration of benzisoxazoles I (R = OH, Cl; R1 = H) gave I (R = OH, Cl; R1 = NO2), and reaction with Br or SO2Cl2 gave I (R = OH, Cl; R1 = Br, Cl). Reduction of I (R = OH, R1 = NO2) with SnCl2 gave I (R = OH, R1 = NH2), which was diazotized and coupled with aromatic amines or phenols to give the azo dyes I (R = OH, R4 = 4-Me2NC6H4N:N, 2-hydroxy-1-naphthylazo). After reading the article, we found that the author used 5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9SDS of cas: 65685-50-9)

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

Kolasa, Krystyna’s team published research in Acta Poloniae Pharmaceutica in 1979 | CAS: 65685-50-9

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.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 unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.Recommanded Product: 65685-50-9

The author of 《Central effects of some new derivatives of benzoxazolin-2-one and 3-hydroxybenzisoxazole》 were Kolasa, Krystyna. And the article was published in Acta Poloniae Pharmaceutica in 1979. Recommanded Product: 65685-50-9 The author mentioned the following in the article:

The title compounds I (R = H or Br; R1 = H, Ac, or CO2Et), II (R = H or Br)and III (R = H or Br) tested in mice at their 1/5, 1/10, 1/20, and 1/40 LD50 dose showed a weak myorelaxant effect and weak inhibitory activity on the central nervous system. In the part of experimental materials, we found many familiar compounds, such as 5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9Recommanded Product: 65685-50-9)

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.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 unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.Recommanded Product: 65685-50-9

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

Ferraris, Dana’s team published research in Journal of Medicinal Chemistry in 2008 | CAS: 65685-50-9

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.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. Application of 65685-50-9 The unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.

Ferraris, Dana; Duvall, Bridget; Ko, Yao-Sen; Thomas, Ajit G.; Rojas, Camilo; Majer, Pavel; Hashimoto, Kenji; Tsukamoto, Takashi published an article in Journal of Medicinal Chemistry. The title of the article was 《Synthesis and Biological Evaluation of D-Amino Acid Oxidase Inhibitors》.Application of 65685-50-9 The author mentioned the following in the article:

D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a full agonist at the glycine site of the NMDA receptor. A series of benzo[d]isoxazol-3-ol derivatives were synthesized and evaluated as DAAO inhibitors. Among them, 6-chlorobenzo[d]isoxazol-3-ol (CBIO) potently inhibited DAAO with an IC50 in the submicromolar range. Oral administration of CBIO in conjunction with D-serine enhanced the plasma and brain levels of D-serine in rats compared to the oral administration of D-serine alone. In the experiment, the researchers used 5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9Application of 65685-50-9)

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.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. Application of 65685-50-9 The unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.

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

Domagalina, Eugenia’s team published research in Acta Poloniae Pharmaceutica in 1980 | CAS: 65685-50-9

5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9) belongs to benzisoxazole.Recommanded Product: 5-Bromobenzo[d]isoxazol-3(2H)-oneThe 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 unique benzisoxazole scaffold also exhibits an impressive potential as antimicrobial, anticancer, anti-inflammatory, anti-glycation agents and so on.

In 1980,Acta Poloniae Pharmaceutica included an article by Domagalina, Eugenia; Gaj, Barbara; Slawik, Tomasz. Recommanded Product: 5-Bromobenzo[d]isoxazol-3(2H)-one. The article was titled 《Arylsulfonyl and sulfanilyl derivatives of benzoxazoles and benzisoxazoles》. The information in the text is summarized as follows:

Benzoxazoles I (R = Cl, Br, R1 = H; R = H, R1 = Cl, Br, SO2NH2; R = Cl, Br, R1 = SO2NH2) and benzisoxazoles II (R = H, Cl, Br, SO2NH2) were prepared in 33-74% yields by treating 2-benzoxazolinones or 3-hydroxybenzisoxazoles, resp., with 4-AcNHC6H4SO2Cl in dioxane containing some Et3N. Similarly, 5-, 6-, and 7-amino-2-benzoxazolinone yielded III. I and III were deacetylated with HCl-EtOH; under similar conditions II yielded sulfanilic acid and the starting benzisoxazole derivative After reading the article, we found that the author used 5-Bromobenzo[d]isoxazol-3(2H)-one(cas: 65685-50-9Recommanded Product: 5-Bromobenzo[d]isoxazol-3(2H)-one)

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