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A Novel Synthesis of 3-Amino-1,2-benzisoxazoles – an Entry into the Isoxazolo<3,4,5-ef><1,4>benzoxazepine Ring System

A novel synthesis of 3-amino-1,2-benzisoxazole (3) from 2-<(isopropylideneamino)oxy>benzonitrile (2) is described.This methodology was used to synthesize 3-amino-4-hydroxy-1,2-benzisoxazole (10), which served as an intermediate for a number of isoxazolo<3,4,5-ef><1,4>benzoxazepines.

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Reference£º
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Simple exploration of Benzo[d]isoxazol-3-amine

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Preparation of 2-hydroxybenzamidines from 3-aminobenzisoxazoles

2-Hydroxybenzamidines have been prepared from 3-aminobenzisoxazoles by reductive cleavage of the nitrogen-oxygen bond using catalytic hydrogenation, Zn/AcOH or NiCl2/NaBH4. This ring-opening reaction can be accomplished chemoselectively in the presence of a variety of hydrogenation-sensitive functional groups including an aryl bromide, benzyl carbamate, and olefin.

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Reference£º
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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Photochemistry of matrix-isolated 3-chloro-1,2-benzisoxazole: Generation and characterization of 2-cyanophenoxyl radical and other reactive intermediates

Photochemistry of 3-chloro-1,2-benzisoxazole 1 in N2 and Ar matrices at 10 K leads to N-chloro-ketenimine 3 and 2-cyanophenyl-hypochlorite 4. The reaction kinetics and the observed photoisomerization of 3 to 4 indicate that ketenimine 3, possibly formed via an elusive vinylnitrene VN, is an intermediate in the formation of hypochlorite 4. A new pathway involving the formation of 2-cyanophenoxyl radical 5, which was captured only in Ar matrix, was also observed. Radical 5 is possibly formed via photodetachment of Cl atom from 1 (or VN) and might explain the formation of 3-chloro-6-oxocyclohexa-1,4-dienecarbonitrile 2 in N2 and Ar matrices. All the species were characterized by IR spectroscopy and theoretical calculations. The computed geometric and electronic structure of radical 5 is discussed. Overall, the results provided further insight into the mechanism of the photochemistry of 1,2-benzisoxazoles and allowed characterization of new interesting reactive intermediates.

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Reference£º
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Properties and Exciting Facts About Benzo[d]isoxazol-3-amine

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Synthesis, SAR study, and biological evaluation of a series of piperazine ureas as fatty acid amide hydrolase (FAAH) inhibitors

A series of piperazine ureas was designed, synthesized, and evaluated for their potential as novel orally available fatty acid amide hydrolase (FAAH) inhibitors that are therapeutically effective against pain. We carried out an optimization study of the lead compound 3 to improve its DMPK profile as well as in vitro potency. We identified the thiazole compound 60j with potent inhibitory activity, high brain permeability, and good bioavailability. Compound 60j showed a potent and dose-dependent anti-nociceptive effect in the acetic acid-induced writhing test in mice.

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Reference£º
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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AMIDE COMPOUND

There is provided a FAAH inhibitor and a prophylactic or therapeutic agent for cerebrovascular disorders or sleep disorders comprising it. The prophylactic or therapeutic agent comprises a compound of the formula (I0): wherein Z is oxygen or sulfur; R1 is aryl which may be substituted, or a heterocyclic group which may be substituted; R1a is a hydrogen atom, a hydrocarbon group which may be substituted, hydroxyl, etc.; R2 is piperidin-1,4-diyl which may be substituted, or piperazin-1,4-diyl which may be substituted; R3 is a group formed by eliminating two hydrogen atoms from a 5-membered aromatic heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, which may be further substituted, -CO-, etc.; and R4 is a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; or a salt thereof.

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Reference£º
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In a patent, 36216-80-5, molecular formula is C7H6N2O, introducing its new discovery. COA of Formula: C7H6N2O

7-AZASPIRO[3.5]NONANE-7-CARBOXAMIDE COMPOUNDS

Provided herein are 7-azaspiro[3.5]nonane-7-carboxamide compounds and the pharmaceutically acceptable salts of such compounds useful in treating diseases or conditions associated with fatty acid amide hydrolase (FAAH) activity, conditions including including acute pain, chronic pain, neuropathic pain, nociceptive pain, inflammatory pain, cancer and cancer pain, fibromyalgia, rheumatoid arthritis, inflammatory bowel disease, lupus, diabetes, allergic asthma, vascular inflammation, urinary incontinence, overactive bladder, emesis, cognitive disorders, anxiety, depression, sleeping disorders, eating disorders, movement disorders, glaucoma, psoriasis, multiple sclerosis, cerebrovascular disorders, brain injury, gastrointestinal disorders, hypertension, or cardiovascular disease

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Reference£º
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Extracurricular laboratory:new discovery of Benzo[d]isoxazol-3-amine

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?In-loop? [11C]CO2 fixation: Prototype and proof of concept

Carbon-11-labeled carbon dioxide is the most common feedstock for the synthesis of positron emission tomography radiotracers and can be directly used for 11C-carbonylation. Herein, we report the development of an apparatus that takes advantage of ?in-loop? technologies to facilitate robust and reproducible syntheses of 11C-carbonyl-based radiotracers by [11C]CO2-fixation. Our ?in-loop? [11C]CO2-fixation method is simple, efficient, and proceeds smoothly at ambient pressure and temperature. We selected model 11C-carbonyl-labeled carbamates as well as symmetrical and unsymmetrical ureas based on their widespread use in radiotracer design and our clinical research interests for proof of concept. Utility of this method is demonstrated by the synthesis of a reversible radiopharmaceutical for monoamine oxidase B, [11C]SL25.1188, and 2 novel fatty acid amide hydrolase inhibitors. These radiotracers were isolated and formulated (>3.5?GBq; 100?mCi) with radiochemical purities (>99%) and molar radioactivity (?80?GBq/mumol; ?2162?mCi/mumol).

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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Novel one-pot cyclization of ortho substituted benzonitriles to 3-amino-1,2-benzisoxazoles

A novel one-pot synthesis of 3-amino-1,2-benzisoxazoles (iii), from ortho substituted benzonitriles (i), is described. The synthesis likely involves a SNAr reaction of an activated ortho halo or nitro group by a hydroxamate anion, followed by an intra-molecular ring closure. 3-Amino-1,2-benzisoxazoles (iii) can be generated quickly in comparable or superior yields via this one-pot procedure when compared to other methods. Reaction parameters and conditions are presented.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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3-Amino-benzo[d]isoxazoles as novel multitargeted inhibitors of receptor tyrosine kinases

A series of benzoisoxazoles and benzoisothiazoles have been synthesized and evaluated as inhibitors of receptor tyrosine kinases (RTKs). Structure-activity relationship studies led to the identification of 3-amino benzo[d]isoxazoles, incorporating a N,N?-diphenyl urea moiety at the 4-position that potently inhibited both the vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor families of RTKs. Within this series, orally bioavailable compounds possessing promising pharmacokinetic profiles were identified, and a number of compounds demonstrated in vivo efficacy in models of VEGF-stimulated vascular permeability and tumor growth. In particular, compound 50 exhibited an ED50 of 2.0 mg/kg in the VEGF-stimulated uterine edema model and 81% inhibition in the human fibrosarcoma (HT1080) tumor growth model when given orally at a dose of 10 mg/kg/day.

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Reference£º
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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QUINUCLIDINE DERIVATIVES AS MUSCARINIC M3 RECEPTOR ANTAGONISTS

The invention provides named compounds of formula (I), wherein R4 is a N-substituted quinuclidine (I) pharmaceutical compositions containing them and a process for preparing the pharmaceutical compositions. Their use in therapy for? the treatment of conditions mediated by M3 muscarinic receptors, such as chronic obstructive pulmonary disease is also disclosed.

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Reference£º
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics