Category: Benzisoxazole

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

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

Li, Meng; Wang, Dong-Hui published the artcile< Copper-Catalyzed 3-Positional Amination of 2-Azulenols with O-Benzoylhydroxylamines>, Application of C12H13FN2O, the main research area is azulenol benzoylhydroxylamine copper catalyst regioselective amination; aminoazulenol preparation.

A copper-catalyzed ortho-selective amination of 2-azulenols with O-benzoylhydroxylamines (RR’N-OBz) to synthesize ortho-aminoazulenols was reported. A wide range of functional groups on amines were compatible, furnishing the corresponding amino-azulene derivatives in moderate to good yields. The further synthetic elaboration using 3-amino-2-azulenols as starting materials was demonstrated.

Organic Letters published new progress about Amination catalysts (regioselective). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Application of C12H13FN2O.

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

Zhang, Ze-Xin; Willis, Michael C. published the artcile< Sulfondiimidamides as new functional groups for synthetic and medicinal chemistry>, Category: benzisoxazole, the main research area is sulfondiimidamide preparation.

Due to their three-dimensional structure, chem. and metabolic stability, polarity, and hydrogen-bonding ability, sulfonamides RS(=NC(CH3)2CH2(CH3)3)(=NNs)R1 (R1 = Et, 4-fluorophenyl, cyclopropyl, pyridin-3-yl, etc. ;NH2, 2-methylpropan-2-aminyl, morpholin-4-yl) occupy a privileged position among the functional groups used to design bioactive mols. The mono aza variants, sulfonimidamides, a functional group known since the 1930s, possess an extra nitrogen atom, which delivers an addnl. point of diversity and introduces chirality at sulfur. The sulfondiimidamides are viable mols. and by using an unsym. sulfurdiimide as a linchpin, in combination with organometallic reagents RMgX (X = Br, Cl) and amines R1NH, their three-component assembly is showed. Variation of the substrates, and the controlled manipulation of nitrogen functionality, allows a broad range of substituents to be introduced at all three nitrogen atoms and at carbon.

Chem published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Category: benzisoxazole.

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

Sivala, Munichandra Reddy; Chintha, Venkataramaiah; Potla, Krishna Murthy; Chinnam, Sampath; Chamarthi, Naga Raju published the artcile< In silico docking studies and synthesis of new phosphoramidate derivatives of 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole as potential antimicrobial agents>, SDS of cas: 84163-77-9, the main research area is phosphoramidate docking studies antimicrobial agents; Phosphoramidates; anti-bacterial activity; anti-fungal activity; benzisoxazole; molecular docking.

A new class of phosphoramidate derivatives of 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole were synthesized in good to excellent yields (78-96%) by an in situ, three-step process. All the synthesized mols. were evaluated for anti-bacterial and anti-fungal activities using in vitro and in silico methods. The results revealed that the compounds , , , , and exhibited the most promising anti-bacterial activity against S. aureus, B. subtilis, K. pneumoniae, S. typhi and P. mirabilis and anti-fungal activity against A. niger and A. flavus when compared with the standard drugs Norfloxacin and Nystatin at concentrations of 25, 50, 75 and 100μg/mL. The rest of the title compounds have shown moderate activity against all the bacterial and fungal strains. Mol. docking studies revealed that the synthesized compounds have exhibited significant binding modes with high dock scores ranging from -7.2 to -9.5 against 3V2B protein when compared with the standard drugs Norfloxacin (-5.8) and Nystatin (-6.6) resp. Hence, it is suggested that the synthesized phosphoramidate derivatives of 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole will stand as the promising antimicrobial drug candidates in future.

Journal of Receptors and Signal Transduction published new progress about Antimicrobial agents. 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

Ling, Fei; Liu, Tao; Xu, Chao; He, Jiaying; Zhang, Wangqin; Ling, Changwu; Liu, Lei; Zhong, Weihui published the artcile< Divergent electrolysis for the controllable coupling of thiols with 1,2-dichloroethane: a mild approach to sulfide and sulfoxide>, Related Products of 84163-77-9, the main research area is chloroethyl sulfide green preparation; thiol dichloroethane electrochem sulfidation; sulfoxide chloroethyl green preparation; dichloroethane thiol electrochem sulfoxidation.

A safe, practical and eco-friendly electrochem. methodol. was reported for the controllable dechloro-coupling of 1,2-dichloroethane (DCE) with thiols, providing value-added β-chloroethyl-sulfides ArSCH2CH2Cl [Ar = Ph, 4-MeC6H4, 2-naphthyl, etc.] and β-chloroethyl-sulfoxides Ar1S(O)CH2CH2Cl [Ar1 = Ph, 2-BrC6H4, 2,4-di-MeC6H3, etc.], which served as versatile building blocks in the efficient late-stage conversion to bioactive mols. The mildness and practicality of this protocol was further demonstrated by the total synthesis of anti-gout drug sulfinpyrazone in a 32% total yield over three steps.

Green Chemistry published new progress about Electrochemical reaction. 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

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>, Recommanded Product: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, 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, Recommanded Product: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

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>, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, 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, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

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>, Quality Control 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, Quality Control 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>, Synthetic Route 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 Societypublished 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, Synthetic Route of 84163-77-9.

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