Tag: M.W=200-250

Wang, Jin-Lin; Liu, Mei-Ling; Zou, Jian-Yu; Sun, Wen-Hui; Liu, Xue-Yuan published the artcile< Copper-Catalyzed Aminoarylation of Alkenes via Aminyl Radical Addition and Aryl Migration>, Safety of 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is amino amide preparation; alkene hydroxylamine copper catalyst aminoarylation.

A new strategy for aminoarylation of alkenes by copper-catalyzed Smiles rearrangement using O-benzoylhydroxylamines as the amine reagent was described.. This method affords various β-amino amide derivatives possessing a quaternary carbon center with wide functional group tolerance and high regioselectivity. The mechanistic studies indicate that the transformation can involve aminyl radical intermediates under acid-free condition.

Organic Letters published new progress about Amino amides Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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

Rojas, Juan J.; Croft, Rosemary A.; Sterling, Alistair J.; Briggs, Edward L.; Antermite, Daniele; Schmitt, Daniel C.; Blagojevic, Luka; Haycock, Peter; White, Andrew J. P.; Duarte, Fernanda; Choi, Chulho; Mousseau, James J.; Bull, James A. published the artcile< Amino-oxetanes as amide isosteres by an alternative defluorosulfonylative coupling of sulfonyl fluorides>, Safety of 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is sulfonyl fluoride amine defluorosulfonylative coupling; amino oxetane chemoselective preparation.

A class of reactions for sulfonyl fluorides to form amino-oxetanes by an alternative pathway to the established SuFEx (sulfonyl-fluoride exchange) click reactivity. A defluorosulfonylation forms planar oxetane carbocations simply on warming. This disconnection, comparable to a typical amidation, will allow the application of vast existing amine libraries. The reaction was tolerant to a wide range of polar functionalities and was suitable for array formats. Ten oxetane analogs of bioactive benzamides and marketed drugs were prepared Kinetic and computational studied support the formation of an oxetane carbocation as the rate-determining step, followed by a chemoselective nucleophile coupling step.

Nature Chemistry published new progress about Activation energy. 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

Johansen, Martin B.; Gedde, Oliver R.; Mayer, Thea S.; Skrydstrup, Troels published the artcile< Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO>, Recommanded Product: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is aromatic trifluoromethyl ketone preparation; aryl bromide trimethyltrifluoromethyl silane carbon monoxide monotrifluoromethylation palladium catalyst; fluorosulfate preparation trimethyltrifluoromethyl silane carbon monoxide monotrifluoromethylation palladium catalyst.

A sequential one-pot preparation of aromatic trifluoromethyl ketones RC(O)CF3 (R = 3,5-dimethoxyphenyl, quinolin-3-yl, 4-adamantylphenyl, etc.) starting from readily accessible aryl bromides/fluorosulfates RX (X = Br, OS(O)2F), the latter easily prepared from the corresponding phenols ROH were reported. The methodol. utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13C-isotopically labeled TFMK by switching to the use of 13COgen.

Organic Letters published new progress about Aromatic alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Favalli, Nicholas; Bassi, Gabriele; Bianchi, Davide; Scheuermann, Jorg; Neri, Dario published the artcile< Large screening of DNA-compatible reaction conditions for Suzuki and Sonogashira cross-coupling reactions and for reverse amide bond formation>, Category: benzisoxazole, the main research area is alkyne pinacol borane boronic acid DNA synthesis carboxylic acid; Suzuki Sonogashira cross coupling reverse amide formation DNA compatible; DNA-compatible reactions; DNA-encoded libraries; Reverse amide bond formation; Sonogashira cross-coupling; Suzuki cross-coupling.

Progress in DNA-encoded chem. library synthesis and screening crucially relies on the availability of DNA-compatible reactions, which proceed with high yields and excellent purity for a large number of possible building blocks. In the past, exptl. conditions have been presented for the execution of Suzuki and Sonogashira cross-coupling reactions on-DNA. In this article, our aim was to optimize Suzuki and Sonogashira reactions, comparing our results to previously published procedures. We have tested the performance of improved conditions using 606 building blocks (including boronic acids, pinacol boranes and terminal alkynes), achieving >70% conversion for 84% of the tested mols. Moreover, we describe efficient exptl. conditions for the on-DNA synthesis of amide bonds, starting from DNA derivatives carrying a carboxylic acid moiety and 300 primary, secondary and aromatic amines, as amide bonds are frequently found in DNA-encoded chem. libraries thanks to their excellent DNA compatibility.

Bioorganic & Medicinal Chemistry published new progress about Boronic acids 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, Category: benzisoxazole.

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

Zhu, Chen; Li, Xinwei; Zhao, Bangyi; Peng, Weiqing; Li, Wei; Fu, Wei published the artcile< Discovery of aryl-piperidine derivatives as potential antipsychotic agents using molecular hybridization strategy>, Product Details of C12H13FN2O, the main research area is hybridization aryl piperidine derivative preparation antipsychotic; 5-HT(2A) receptor antagonist; Antipsychotic; D(2) receptor antagonist; Molecular hybridization; Multi-target strategy.

Schizophrenia is a chronic, disabling mental disorder that affects about one percent of world’s population. Drugs acting on multiple targets have been demonstrated to provide superior efficacy in schizophrenia than agents acting on single target. In this study, based on FW01, a selective potent 5-HT1A receptor agonist discovered via dynamic pharmacophore-based virtual screening, mol. hybridization strategy was employed to optimize its in vitro activity over D2 and 5-HT2A receptors. The optimized compound 9f was found to show dual potent D2 and 5-HT2A receptors antagonistic activity. In addition, compound 9f showed good in vivo metabolic stability with t1/2 of 2 h in ICR mice and good capability to penetrate the blood-brain barrier with Kp value of 4.03. These results demonstrated that the dual D2 and 5-HT1A receptor antagonist 9f could serve as a promising lead compound to discover potent antipsychotic agents.

European Journal of Medicinal Chemistry published new progress about 5-HT2A antagonists. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Product Details of C12H13FN2O.

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

Greed, Stephanie; Briggs, Edward L.; Idiris, Fahima I. M.; White, Andrew J. P.; Luecking, Ulrich; Bull, James A. published the artcile< Synthesis of Highly Enantioenriched Sulfonimidoyl Fluorides and Sulfonimidamides by Stereospecific Sulfur-Fluorine Exchange (SuFEx) Reaction>, Related Products of 84163-77-9, the main research area is enantioenriched sulfonimidoyl fluoride sulfonimidamide preparation stereospecific SuFEx; SuFEx reactions; chirality; sulfonimidamides; sulfur; synthetic methods.

Sulfonimidamides present exciting opportunities as chiral isosteres of sulfonamides, with potential for addnl. directional interactions. Here the authors present the first modular enantioselective synthesis of sulfonimidamides, including the first stereoselective synthesis of enantioenriched sulfonimidoyl fluorides, and studies on their reactivity. A new route to sulfonimidoyl fluorides is presented from solid bench-stable, N-Boc-sulfinamide salt building blocks. Enantioenriched arylsulfonimidoyl fluorides are shown to be readily racemized by fluoride ions. Conditions are developed, which trap fluoride and enable the stereospecific reaction of sulfonimidoyl fluorides with primary and secondary amines (100% es) generating sulfonimidamides with up to 99% ee. Aryl and alkyl sulfonimidoyl fluoride reagents are suitable for mild late stage functionalization reactions, exemplified by coupling with a selection of complex amines in marketed drugs.

Chemistry – A European Journal published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation) (sulfonimidamides). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Related Products of 84163-77-9.

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

Porcs-Makkay, Marta; Gyujto, Imre; Lukacs, Gyula; Komaromi, Anna; Toth, Gabor; Garadi, Zsofia; Simig, Gyula; Volk, Balazs published the artcile< Synthesis, Alkylation and Reduction of 4-Aryl-2H-1,2,3-benzothiadiazine 1,1-dioxides>, Related Products of 84163-77-9, the main research area is aryl benzothiadiazine dioxide preparation alkylation hydrogenation allosteric modulator activity; aromatic chlorosulfonyl ketal heterocyclization.

The compound ortho-(2-Aryl-1,3-dioxolan-2-yl)benzenesulfonyl chlorides I (R = Ph, 3-ClC6H4, 3-ClC6H4, etc.; X = H, Cl, OMe; Y = H, Cl) obtained from benzophenone ketals II by directed ortho-lithiation chem. were cyclized either with hydrazine monohydrate or with acetohydrazide to furnish variously substituted 4-aryl-2H-1,2,3-benzothiadiazine 1,1-dioxides III. Alkylation of benzothiadiazine dioxides with alkyl iodides R1I (R1 = Me, Et, n-butyl) under basic conditions was elaborated, revealing significant differences compared to the reactivity of 4-unsubstituted ones IV. Hydrogenation of the C=N double bond in the presence of platinum(IV) oxide is also described. Detailed NMR studies and DFT calculations supported the structure elucidation of the compds IV (X = Cl; Y = Cl; R = Ph; R1 = Me) and 7,8-dichloro-3-methyl-1-oxo-4-phenyl-2H-1,2,3-benzothiadiazin-3-ium-1-olate.

ChemistrySelect published new progress about Alkylation. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Related Products of 84163-77-9.

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

Li, Feng; Wu, Ziyan; Wang, Jingjing; Zhang, Siyuan; Yu, Jiaxin; Yuan, Zhen; Liu, Jingya; Shen, Renzeng; Zhou, Yao; Liu, Lantao published the artcile< Metal-free synthesis of N-sulfonylformamidines via skeletal reconstruction of sulfonyl oximonitriles>, Computed Properties of 84163-77-9, the main research area is sulfonylformamidine preparation diastereoselective; secondary amine sulfonyl oximonitrile tandem reaction.

For the first time, an unprecedented domino reaction of sulfonyl oximonitriles C6H5CH2ON=C(CN)S(O)2Ar (Ar = Ph, 4-methylphenyl) with secondary amines such as morpholine, bis(propan-2-yl)amine, pyrrolidine, etc. to streamline the synthesis of N-sulfonylformamidines, e.g., I, in decent to high yields under mild reaction conditions was developed. In addition, scale-up experiments and late-stage functionalization of drugs were also performed. Preliminary studies indicate that the loss of a cyano-/benzyloxy-group and a sulfonyl migration process are involved in this reaction.

Organic Chemistry Frontiers published new progress about Benzenesulfonamides Role: SPN (Synthetic Preparation), PREP (Preparation). 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

Jin, Jian; Zhang, Kunxiao; Dou, Fei; Hao, Chao; Zhang, Yifang; Cao, Xudong; Gao, Lanchang; Xiong, Jiaying; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen; Chen, Yin published the artcile< Isoquinolinone derivatives as potent CNS multi-receptor D2/5-HT1A/5-HT2A/5-HT6/5-HT7 agents: Synthesis and pharmacological evaluation>, Application of C12H13FN2O, the main research area is benzoisoxazolyl piperidinyl isoquinolinone preparation multi receptor SAR; aryl piperazinyl isoquinolinone preparation multi receptor SAR; Atypical antipsychotics; Isoquinolinone; Multi-receptor; Piperidine.

IA series of novel Isoquinolinone derivatives were synthesized as potential multi-target antipsychotics. Among these, compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one showed high affinity for dopamine D2 and serotonin 5-HT1A, 5-HT2A, 5-HT6, and 5-HT7 receptors, showed low affinity for off-target receptors (5-HT2C, H1, and α1), and negligible effects on ether-a-gogo-related gene (hERG; i.e., reduced QT interval prolongation). An animal behavioral study revealed that compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one reversed APO-induced hyperlocomotion, MK-801-induced hyperactivity, and DOI-induced head twitch. Moreover, compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one exhibited a high threshold for acute toxicity, a lack of tendency to induce catalepsy, and did not cause prolactin secretion or weight gain when compared to risperidone. Furthermore, in the forced swim test, tail suspension test, and novel object recognition test, treatment with compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one resulted in improvements in depression and cognitive impairment. In addition, compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one was favorable pharmacokinetic profile in rats. Thus, the antipsychotic drug-like effects of compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one indicate that it was useful for developing a novel class of drugs for the treatment of schizophrenia.

European Journal of Medicinal Chemistry 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, Application of C12H13FN2O.

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

Zhou, Wu-Xi; Chen, Chen; Liu, Xiao-Qin; Li, Ying; Kong, Ling-Yi; Luo, Jian-Guang published the artcile< Synthesis and biological evaluation of novel withangulatin A derivatives as potential anticancer agents>, Product Details of C12H13FN2O, the main research area is withangulatin A derivative preparation anticancer structure activity; Anticancer; Apoptosis; Cell cycle; Reactive oxygen species; Withangulatin A derivatives.

Novel withangulatin A (WA) derivatives were synthesized and evaluated for antiproliferative activity against four human cancer cell lines (U2OS, MDA-MB-231, HepG2, and A549). Among these derivatives, I exhibited the most potent antiproliferative activity, with an IC50 value of 74.0 nM against the human breast cancer cell line MDA-MB-231 and potency that was 70-fold that of WA (IC50 = 5.22μM). Moreover, I caused G2-phase cell cycle arrest in a concentration-dependent manner and induced the apoptosis of MDA-MB-231 cells by increasing intracellular reactive oxygen species (ROS). Compound I showed a high selectivity index (SI = 267.03) for breast cancer MDA-MB-231 cells. These results suggest that I is a promising anticancer agent.

Bioorganic Chemistry published new progress about Anti-apoptotic agents. 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Product Details of C12H13FN2O.

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