Month: October 2022

Yao, Zhi-Li; Wang, Lei; Shao, Nan-Qi; Guo, Yin-Long; Wang, Dong-Hui published the artcile< Copper-Catalyzed ortho-Selective Dearomative C-N Coupling of Simple Phenols with O-Benzoylhydroxylamines>, Formula: C12H13FN2O, the main research area is aminocyclohexadienone regioselective preparation; copper catalyst regioselective dearomative coupling phenol benzoylhydroxylamine; mechanism lack radical inhibition dearomative coupling phenol benzoylhydroxylamine.

In the presence of Cu(OTf)2 and LiOt-Bu in THF, 2,6-disubstituted phenols such as 2,6-dimethylphenol underwent regioselective dearomative coupling reactions with secondary O-benzoylhydroxylamines such as 4-(benzoyloxy)morpholine to yield aminocyclohexadienones such as I. Lack of inhibition with radical trapping agents, lack of rearrangement with a cyclopropylated phenol, and mass spectrometric detection of intermediates in the reaction support a mechanism involving either a single-electron transfer process involving attack of an N-centered radical onto the phenol or a two-electron pathway involving addition of phenol to an electrophilic Cu(III)-amino complex via an inner-sphere process.

ACS Catalysis published new progress about Amines, keto Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (aminocyclohexadienones). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Formula: C12H13FN2O.

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

Zhou, Xueying; Xu, Yaling; Wang, Caihong; Wu, Ge published the artcile< Cu-catalyzed vinylamination of S-alkylisothiouronium salts with maleimides and alkylamines>, HPLC of Formula: 84163-77-9, the main research area is aminoalkylthiolated maleimide preparation; alkylisothiouronium salt maleimide alkylamine vinylamination copper catalyst.

A copper-catalyzed vinylamination of S-alkylisothiouronium salts with maleimide and organic amines with the assistance of FeCl3, enabling the preparation of structurally diverse aminoalkylthiolated maleimides and applying them to late-stage modification of pharmaceuticals is reported. Importantly, this strategy makes it possible to introduce the SCD3 functional group into the maleimide skeleton by using the prepared S-trideuteromethyl isothiouronium iodide. Preliminary mechanistic investigation shows that FeCl3 is essential to the current multi-component reaction by triggering S-alkylisothiouronium salts.

Applied Organometallic Chemistry published new progress about Amination. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, HPLC of Formula: 84163-77-9.

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

Huang, Ling; Gao, Lanchang; Zhang, Xiaohua; Yin, Lei; Hu, Jintao; Song, Ting; Chen, Yin published the artcile< Synthesis and pharmacological evaluation of piperidine (piperazine)-amide substituted derivatives as multi-target antipsychotics>, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is piperidine piperazine amide derivative antipsychotic; Amide; Antipsychotic; Multi-target; Piperazine; Piperidine.

We report the optimization of a series of novel amide-piperidine (piperazine) derivatives using the multiple ligand approach with dopamine and serotonin receptors. Of the derivatives, compound 11 (I) exhibited high affinity for the D2, 5-HT1A, and 5-HT2A receptors, but low affinity for the 5-HT2C and histamine H1 receptors and human ether-a-go-go-related gene (hERG) channels. In vivo, compound 11 reduced apomorphine-induced climbing, MK-801-induced hyperactivity and DOI-induced head twitching without observable catalepsy, even at the highest dose tested. In addition, it exhibited suppression in a CAR test. Furthermore, in a novel object recognition task, it displayed pro-cognition properties. Therefore, compound 11 is a promising candidate multi-target antipsychotic.

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT1A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 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

Pedersen, Simon S.; Donslund, Aske S.; Mikkelsen, Jesper H.; Bakholm, Oskar S.; Papp, Florian; Jensen, Kim B.; Gustafsson, Magnus B. F.; Skrydstrup, Troels published the artcile< A Nickel(II)-Mediated Thiocarbonylation Strategy for Carbon Isotope Labeling of Aliphatic Carboxamides>, Computed Properties of 84163-77-9, the main research area is aliphatic carboxamide preparation; alkyl zinc halide methyldiphenylsilanecarboxylic acid amine thiocarbonylation nickel catalyst; aliphatic carboxamides; aminocarbonylation; isotope labeling; nickel; thioesters.

A series of pharmaceutically relevant small mols. and biopharmaceuticals bearing aliphatic carboxamides have been successfully labeled with carbon-13. Key to the success of this novel carbon isotope labeling technique is the observation that 13C-labeled Ni(II)-acyl complexes, formed from a 13CO insertion step with Ni(II)-alkyl intermediates, rapidly react in less than one minute with 2,2′-dipyridyl disulfide to quant. form the corresponding 2-pyridyl thioesters. Either the use of 13C-SilaCOgen or 13C-COgen allows for the stoichiometric addition of isotopically labeled carbon monoxide. Subsequent one-pot acylation of a series of structurally diverse amines provides the desired 13C-labeled carboxamides in good yields. A single electron transfer pathway is proposed between the Ni(II)-acyl complexes and the disulfide providing a reactive Ni(III)-acyl sulfide intermediate, which rapidly undergoes reductive elimination to the desired thioester. By further optimization of the reaction parameters, reaction times down to only 11 min were identified, opening up the possibility of exploring this chem. for carbon-11 isotope labeling. Finally, this isotope labeling strategy could be adapted to the synthesis of 13C-labeled liraglutide and insulin degludec, representing two antidiabetic drugs.

Chemistry – A European Journal published new progress about Acylation. 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

Krol, Marek; Slifirski, Grzegorz; Kleps, Jerzy; Ulenberg, Szymon; Belka, Mariusz; Baczek, Tomasz; Siwek, Agata; Stachowicz, Katarzyna; Szewczyk, Bernadeta; Nowak, Gabriel; Duszynska, Beata; Herold, Franciszek published the artcile< Synthesis of novel pyrido[1,2-c]pyrimidine derivatives with 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole moiety as potential SSRI and 5-HT1A receptor ligands>, Quality Control of 84163-77-9, the main research area is pyridopyrimidine piperidinyl benzisoxazole preparation hydroxytryptamine receptor serotonin transporter ligand; antidepressants; drug design; dual 5-HT1A/SERT activity; pyrido[1,2-c]pyrimidines.

Two series of novel 4-aryl-2H-pyrido[1,2-c]pyrimidines I (R = Ph, 2-MeC6H4, 4-MeOC6H4, 4-FC6H4, etc.) and 4-aryl-5,6,7,8-tetrahydropyrido[1,2-c]pyrimidines II (R as above) were synthesized. The chem. structures of the new compounds were confirmed by 1H and 13C NMR spectroscopy and ESI-HRMS spectrometry. The affinities of all compounds for the 5-HT1A receptor and serotonin transporter protein (SERT) were determined by in vitro radioligand binding assays. The test compounds demonstrated very high binding affinities for the 5-HT1A receptor of all derivatives in the both series and generally low binding affinities for the SERT protein, with the exception of compounds I (R = Ph) and II (R = 4-MeOC6H4). Extended affinity tests for the receptors D2, 5-HT2A, 5-HT6 and 5-HT7 were conducted with regard to selected compounds I (R = Ph, 2-ClC6H4) and II (R = 4-MeOC6H4, 4-FC6H4). All four compounds demonstrated very high affinities for the D2 and 5-HT2A receptors. Compounds I (R = Ph) and II (R = 4-MeOC6H4) also had high affinities for 5-HT7, while I (R = 2-ClC6H4) and II (4-FC6H4) held moderate affinities for this receptor. Compounds I (R = Ph) and II (R = 4-MeOC6H4) were also tested in vivo to identify their functional activity profiles with regard to the 5-HT1A receptor, with I (R = Ph) demonstrating the activity profile of a presynaptic agonist. Metabolic stability tests were also conducted for the compounds I (R = Ph, 2-ClC6H4).

International Journal of Molecular Sciences published new progress about 5-HT1A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 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

Gao, Lanchang; Yang, Zhengge; Xiong, Jiaying; Hao, Chao; Ma, Ru; Liu, Xin; Liu, Bi-Feng; Jin, Jian; Zhang, Guisen; Chen, Yin published the artcile< Design, synthesis and biological investigation of flavone derivatives as potential multi-receptor atypical antipsychotics>, SDS of cas: 84163-77-9, the main research area is flavone preparation antipsychotic dopamine serotonin receptor; atypical antipsychotics; dopamine; multi-target; serotonin.

The design of a series of novel flavone derivatives I (X = N, CH; Ar = 2-methoxyphenyl, 6-fluorobenzo[d]isoxazol-3-yl, pyrimidin-2-yl, etc.; n = 1, 2), II (m = 1, 2) and III (R1 = H, Cl; R2 = H, Me) was synthesized as potential broad-spectrum antipsychotics by using multi-receptor affinity strategy between dopamine receptors and serotonin receptors. Among them, I (X = CH, Ar = 6-fluorobenzo[d]isoxazol-3-yl, n = 2), (IV) exhibited a promising preclin. profile. Compound IV not only showed high affinity for dopamine D2, D3, and serotonin 5-HT1A, 5-HT2A receptors, but was also endowed with low to moderate activities on 5-HT2C, α1, and H1 receptors, indicating a low liability to induce side effects such as weight gain, orthostatic hypotension and QT prolongation. In vivo behavioral studies suggested that compound IV has favorable effects in alleviating the schizophrenia-like symptoms without causing catalepsy. Taken together, compound V has the potential to be further developed as a novel atypical antipsychotic.

Molecules published new progress about 5-HT1A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, SDS of cas: 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