Category: 84163-77-9

Gu, Zheng-Song; Wang, Wen-Tao; Qian, Hao; Zhou, Ai-Nan; Sun, Hong-Bin; Zhang, Qing-Wei; Li, Jian-Qi published the artcile< Synthesis and antidepressant effect of novel aralkyl piperazine and piperidine derivatives targeting SSRI/5-HT1A/5-HT7>, Recommanded Product: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is aralkyl piperazine piperidine antidepressant SSRI 5HT1A 5HT7 target; 5-HT(1A) receptor; 5-HT(7) receptor; Antidepressant; Serotonin reuptake inhibition.

A series of novel aralkyl piperazine and piperidine derivatives were synthesized, and evaluated for their serotonin reuptake inhibitory and 5-HT1A/5-HT7 receptors affinities activity. Antidepressant activities in vivo of the selective compound were screened using the forced swimming test (FST) and tail suspension test (TST). The results indicated that compound 19a (I) exhibited high affinities for the 5-HT1A/5-HT7 receptors (5-HT1A, Ki = 12 nM; 5-HT7, Ki = 3.2 nM) coupled with potent serotonin reuptake inhibition (IC50 = 14 nM) and showed a marked antidepressant-like effect in the FST and TST models.

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT reuptake inhibitors. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Recommanded Product: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

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

Gao, Lanchang; Hao, Chao; Chen, Jiali; Ma, Ru; Zheng, Lu; Wu, Qingkun; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen; Chen, Yin; Jin, Jian published the artcile< Discovery of a new class of multi-target heterocycle piperidine derivatives as potential antipsychotics with pro-cognitive effect>, Electric Literature of 84163-77-9, the main research area is benzoisoxazolyl piperidine synthesis antipsychotic procognitive; Atypical antipsychotics; Cognition; Dopamine; Multi-target; Serotonin.

A series of benzoisoxazolylpiperidine derivatives were synthesized by using the multi-target strategies and their potent affinities for dopamine (DA), serotonin (5-HT) and human histamine H3 receptors have been evaluated. Of these compounds, the promising candidate 4w (I) displayed high affinities for D2, D3, 5-HT1A, 5-HT2A and H3, a moderate affinity for 5-HT6, negligible effects on the human ether-a-go-go-related gene (hERG) channel, low affinities for off-target receptors (5-HT2C, adrenergic α1 and H1). In addition, the animal behavioral study revealed that, compared to risperidone, compound 4w significantly inhibited apomorphine-induced climbing and MK-801-induced movement behaviors with a high threshold for catalepsy and low liabilities for weight gain and hyperprolactinemia. Results from the conditioned avoidance response test and novel object recognition task demonstrated that 4w had pro-cognitive effects. Thus, the antipsychotic drug-like activities of 4w indicate that it may be a potential polypharmacol. antipsychotic candidate drug.

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT1A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (receptor affinity). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Electric Literature of 84163-77-9.

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

Lu, Bin; Xu, Minghao; Qi, Xiaotian; Jiang, Min; Xiao, Wen-Jing; Chen, Jia-Rong published the artcile< Switchable Radical Carbonylation by Philicity Regulation>, Application In Synthesis of 84163-77-9, the main research area is amide preparation; ketoamide preparation; aryl amine cyclicbutane oxime ester carbon monoxide carbonylation photocatalyst.

A new strategy that exploits photoredox catalysis to regulate the philicity of amine coupling partners to drive switchable radical carbonylation reactions was described. In double carbonylation, amines e.g., aniline were first transformed into nitrogen radical cations by single-electron transfer-oxidation and coupled with CO to form carbamoyl radicals, which further underwent radical cross-coupling with the incipient cyanoalkyl acyl radicals to afford the double carbonylation products. Upon the addition of stoichiometric 4-dimethylaminopyridine (DMAP), DMAP competitively traps the initially formed cyanoalkyl acyl radical to form the relatively stabilized cyanoalkyl acyl-DMAP salts that engaged in the subsequent substitution with the nucleophilic amines to produce the single carbonylation products. The reaction proceeded smoothly with excellent selectivity in the presence of various amine nucleophiles at room temperature, generating valuable amides e.g., 4-cyano-N-phenylbutanamide and α-ketoamides e.g., 5-cyano-2-oxo-N-phenylpentanamide in a versatile and controlled fashion. Combined exptl. and computational studies provided mechanistic insights into the possible pathways.

Journal of the American Chemical Society published new progress about Amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Application In Synthesis of 84163-77-9.

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

Kumar, Roopender; Floden, Nils J.; Whitehurst, William G.; Gaunt, Matthew J. published the artcile< A general carbonyl alkylative amination for tertiary amine synthesis>, Safety of 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is tertiary amine preparation carbonyl alkylative amination.

The ubiquity of tertiary alkylamines in pharmaceutical and agrochem. agents, natural products and small-mol. biol. probes has stimulated efforts towards their streamlined synthesis. Arguably the most robust method for the synthesis of tertiary alkylamines is carbonyl reductive amination, which comprises two elementary steps: the condensation of a secondary alkylamine with an aliphatic aldehyde to form an all-alkyl-iminium ion, which is subsequently reduced by a hydride reagent. Direct strategies were sought for a ‘higher order’ variant of this reaction via the coupling of an alkyl fragment with an alkyl-iminium ion that was generated in situ. However, despite extensive efforts, the successful realization of a ‘carbonyl alkylative amination’ has not yet been achieved. Here the authors present a practical and general synthesis of tertiary alkylamines through the addition of alkyl radicals to all-alkyl-iminium ions. The process is facilitated by visible light and a silane reducing agent, which trigger a distinct radical initiation step to establish a chain process. This operationally straightforward, metal-free and modular transformation forms tertiary amines, without structural constraint, via the coupling of aldehydes and secondary amines with alkyl halides. The structural and functional diversity of these readily available precursors provides a versatile and flexible strategy for the streamlined synthesis of complex tertiary amines.

Nature (London, United Kingdom) published new progress about Aliphatic aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Safety of 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

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

Marganakop, Sheetal B.; Kamble, Ravindra R.; Sannaikar, Madivalagouda S.; Bayannavar, Praveen K.; Kumar, S. Madan; Inamdar, Sanjeev R.; Shirahatti, Arunkumar M.; Desai, Saleem M.; Joshi, Shrinivas D. published the artcile< SCXRD, DFT and molecular docking based structural analyses towards novel 3-piperazin-1-yl-benzo[d]isothiazole and 3-piperidin-4-yl-benzo[d]isoxazoles appended to quinoline as pharmacological agents>, Safety of 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is quinoline piperazinyl benzoisothiazole benzoisoxazole preparation antibacterial antifungal DFT; bromomethyl chloroquinoline benzothiazole benzoxazole nucleophilic substitution reaction.

Novel quinoline containing 3-piperazin-1-yl-benzo[d]isothiazoles and 3-piperidin-4-yl-benzo[d]isoxazole were synthesized. Hirshfeld surface, electrostatic potential maps were obtained resp. from SCXRD and DFT studies. These compounds were analyzed for in vitro antimicrobial activity and correlated with energy difference (ΔE) between HOMO and LUMO energy levels obtained from DFT and correlated with ΔE of standard drug to explain the activity. Further the antimicrobial activity was corroborated by docking against various target enzymes. The present work provided some hints for developing novel antimicrobial quinoline derivatives

Journal of Molecular Structure published new progress about Antibacterial agents. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Safety of 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

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

Paul, Anirudra; Seidel, Daniel published the artcile< α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines>, COA of Formula: C12H13FN2O, the main research area is cyclic secondary amine alpha functionalization Lewis acid organometallic imine.

Cyclic imines, generated in situ from their corresponding N-lithiated amines and a ketone hydride acceptor, undergo reactions with a range of organometallic nucleophiles to generate α-functionalized amines in a single operation. Activation of the transient imines by Lewis acids that are compatible with the presence of lithium alkoxides is crucial to accommodate a broad range of nucleophiles including lithium acetylides, Grignard reagents, and aryllithiums with attenuated reactivities.

Journal of the American Chemical Society published new progress about Alkali metal alkoxides, lithium alkoxides Role: RGT (Reagent), RACT (Reactant or Reagent). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, COA of Formula: C12H13FN2O.

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

Sarva, Santhisudha; Gundluru, Mohan; Kolathur, Vasudha; Cirandur, Suresh Reddy published the artcile< Green synthesis and antimicrobial activities of diphenyl substituted aryl phosphoramidates>, Quality Control of 84163-77-9, the main research area is diphenyl aryl phosphoramidate green preparatn antimicrobial activity.

A green, facile and an efficient protocol has been used for the synthesis of new series of di-Ph substituted aryl phosphoramidates by the reaction of di-Ph phosphoryl chloride and various primary/secondary amines using THF as solvent. 1,4-dimethylpiperazine (DMP) was entrenched as a suitable base for catalyzing the formation of a P-N linkage. 1H-NMR, 13C-NMR, 31P-NMR and mass spectral studies were used to characterize all the title compounds The newly synthesized phosphoramidates were screened for their antimicrobial activity. Most of the compounds depicted good to moderate antimicrobial activity when compared to the standard

Organic Communications published new progress about Antibacterial agents. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Quality Control of 84163-77-9.

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

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.

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.

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

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.

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.

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

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