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Different 7-amino-3-methyl-5-(3′-aryl prop-2′-enoyl)-1,2-benzisoxazoles were synthesized by the interaction of appropriate 5-acetyl-7-amino-3-methyl-1,2-benzisoxazole with different aromatic aldehydes using piperidine. Tetra-O-acetyl-alpha-D-glucopyranosyl bromide was prepared by the reaction of powdered glucose pentaacetate and bromine in the presence of chloroform. Condensation of tetra-O-acetyl-alpha-D-glucopyranosyl bromide with 7-amino-3-methyl-5-(3′-aryl prop-2′-enoyl)-1,2-benzisoxazoles furnished 7-amino-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3-methyl-5-(3′-aryl prop-2′-enoyl)-1,2-benzisoxazoles which on deprotection gave 7-amino-(beta-D-glucopyranosyl)-3-methyl-5-(3′-aryl prop-2′-enoyl)-1,2-benzisoxazoles. Polarographic studies revealed the presence of reducible groups with distinguished E-1/2 values. All compounds were screened for antimicrobial activities, and some compounds showed potent antibacterial and antifungal activities. [GRAPHICS]

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

8-Sep-2021 News You Should Know Something about C4H6O3

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A series of 2-hydroxyaryl ketoximes were converted to the corresponding 1,2-benzisoxazole 2-oxides by treatment with iodobenzene diacetate (in acetic acid or methanol) or N-chlorosuccinimide in water. Both methods gave moderate to excellent yields for a variety of substituted oximes under mild conditions within short reaction times. The latter method has the advantages of an aqueous solvent and lack of halogenated organic by-products.

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

2 Sep 2021 News What Kind of Chemistry Facts Are We Going to Learn About C4H6O3

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The use of molecularly imprinted polymers in synthetic organic chemistry is reviewed. These materials are prepared in the presence of a template for which they carry a functional and stereochemical memory and can be likened to artificial antibodies or enzymes. Their unique properties have been exploited by the use of imprinted polymers as stereo- and regio-selective solid supports in condensation reactions and hydride reduction, as protecting groups in the acylation of polyols and as catalysts to enhance the rates of reactions as diverse a Diels-Alder reaction, an Aldol condensation, beta-elimination, the benzisoxazole isomerization, transesterification and ester hydrolyses.

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

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Plant regeneration from explant and protoplast derived callus has been achieved in Medicago littoralis cv. Harbinger 1886, an annual legume resistant to the fungus Pseudopeziza medicaginis. Callus was induced from different tissue explants and the fastest growth rate was observed for hypocotyls in B5 medium with 2 mg l(-1) 2,4-dichlorophenoxyacetic acid and 0.5 mg l(-1) N-6-benzyladenine. Protoplasts were isolated from cotyledons and leaves of sterile plants and from callus; the first two kinds of protoplasts showed a plating efficiency of 5.6% and 5%, respectively, when embedded in agarose. Plant regeneration occurred on media containing N-6-Delta(2)isopentenyl-adenine combined with indole-3-acetic acid or 1,2-benzisoxazole-3-acetic acid, and on media with N-6-benzyladenine plus alpha-naphtaleneacetic acid; a cytokinin/auxin ratio higher than 1 induced embryos while a ratio around 1 stimulated shoot formation. Embryo development and rooting of shoots were performed in RL medium without growth regulators.

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

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Objectives: Zonisamide (1,2-benzisoxazole-3-methanesulfonamide) is a novel antiseizure medication approved for use in the United States as adjunct therapy in the treatment of partial seizures in adults with epilepsy. It has also been used to treat other conditions including intractable pain. The aim of this study was to determine the usefulness of zonisamide in patients whose seizures were not controlled after having been treated with at least three other currently available anticonvulsant medications or in patients whose pain control was suboptimal despite the use of commonly used drug regimens. Methods: This was a retrospective study documenting the efficacy of zonisamide in 48 consecutive patients who presented at an outpatient neurology clinic at a Veterans Administration hospital. The patients were diagnosed with refractory partial seizures (n = 21) or a variety of intractable neuropathic pain syndromes (n = 27). Results: Sixteen out of 21 seizure patients (76%) experienced a 50% or greater reduction in seizure frequency when zonisamide (1100-200 mg daily) was added to their existing anticonvulsant medication regimen. Of 27 patients with neuropathic pain, 17 (59%) responded to zonisamide, reporting subjective reduction in pain by at least 50%. The most common adverse events were gastrointestinal upset, somnolence, and one case of skin rash. Conclusions: In this study, zonisamide appeared to be an effective adjunct therapy in the treatment of partial seizures in adults who continued to experience frequent episodes while taking other anticonvulsant medications, and in adults whose neuropathic pain was not well controlled with analgesics. These promising results must be tempered by the fact that this investigation included a small patient population in an uncontrolled study design. Further research into the efficacy and tolerability of zonisamide in these areas is warranted.

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Reference:
Benzisoxazole – Wikipedia,
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Further exploration of the scope of our solid-phase method for the synthesis of 3 -aminobenzisoxazoles (using the Kaiser oxime resin 1) is described. The effects of base, leaving group, and solvent on the nucleophilic aromatic substitution based resin-loading reaction are discussed. Representative aryloxime intermediates were subjected to a variety of acidic conditions commonly used in protecting group removal to establish the acid stability profile of this linker. Regioselectivity was evaluated with various di- and trifluorobenzonitriles, which gave single benzisoxazole products after loading and cyclorelease reactions. Substituent effects observed in the course of the acid stability and regioselectivity studies suggest that the nitrile plays a critical role in the oxime hydrolysis mechanism. Finally, to establish the compatibility of the aryloxime linker with a variety of useful on-resin synthetic transformations, functionalized substrates were loaded onto resin 1, and carbon-nitrogen, carbon-oxygen, and carbon-carbon bond-forming reactions were successfully executed.

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

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The spontaneous decarboxylation of 6-nitrobenzisoxazole-3-carboxylate ion is strongly catalysed by micelles of zwitterionic surfactants, viz., sulfobetaines [C(14)H(29)N(+)R(2)(CH2)(3)SO3-, R = Me, Pr and C16H33 N(+)Me(2)(CH2)(3)SO3-] and amine oxides (C(14)H(29)N(+)R(2)O(-), R = Me, Pr), with rates enhanced by factors of up to 1800. These micelles and those of the corresponding carboxybetaines are more effective catalysts than those of the corresponding cationic surfactants, In all cases a change from Me to Pr at the head group speeds reaction by factors of ca. 5-8 for the sulfobetaines and amine oxides and ca. 14 for the cationic surfactants. Cyclizations of the o-3-halopropyloxyphenoxide ions (halogen = Br, I), which are intramolecular S(N)2 reactions, are modestly micellar catalysed, but structural effects on the micellar catalysis by cationic and betaine surfactants are in the same sequence, as for decarboxylation.

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

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4-(2-Hydroxybenzoyl)-1-phenylpyrazole (1) has been used in the synthesis of benzofuran (2), coumarin (5) and benzisoxazole (9).

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

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The benzisoxazole and pyrimidine moieties are essentially planar and the dihedral angle between these planes is 5.6 (1)-degrees. The piperidine ring is in a slightly distorted chair conformation, while the tetrahydropyridine moiety shows a half-chair conformation. The crystal stucture is stabilized by a hydrogen bond between the H atom on position 4 of the benzisoxazole and the O atom of the pyrimidinone of a translated (x, y-1, z) molecule [C…O = 3.372 (7), H…O = 2.327 angstrom, C-H…O = 161.6-degrees].

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

Extracurricular laboratory: Discover of C4H6O3

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Zonisamide, a widely available antiepileptic drug, has been approved in Japan as adjunctive therapy with levodopa for the treatment of previously treated patients with Parkinson’s disease. It is an oral 1,2-benzisoxazole-3-methanesulfonamide and is associated with increased striatal dopamine levels in animal models. In two 12-week, randomized, double-blind, multi-centre trials in adult patients with inadequately controlled Parkinson’s disease and receiving levodopa, zonisamide 25 mg once daily (the recommended dosage) significantly improved motor function from baseline at final assessment, as assessed by the Unified Parkinson’s Disease Rating Scale (UPDRS) Part III total score (primary endpoint), compared with placebo. Zonisamide 25 mg once daily as adjunctive therapy with levodopa was generally well tolerated by patients with Parkinson’s disease. The overall incidence of adverse events was not significantly different between zonisamide 25mg once daily and placebo groups in the phase IIb/III trial.

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