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SYNTHESIS OF 1,2-BENZISOXAZOLE 2-OXIDES

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

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Role of Water in the Multifaceted Catalytic Antibody 4B2 for Allylic Isomerization and Kemp Elimination Reactions

Specificity toward a single reaction is a well-known characteristic of catalytic antibodies. However, contrary to convention, catalytic antibody 4B2 possesses the ability to efficiently catalyze two unrelated reactions: a Kemp elimination and an allylic isomerization of a beta,gamma-unsaturated ketone. To elucidate how this multifaceted antibody operates, mixed quantum and molecular mechanics calculations coupled to Monte Carlo simulations were carried out. The antibody was determined to derive its adaptability for the mechanistically different reactions through the rearrangement of water molecules in the active site into advantageous geometric orientations for enhanced electrostatic stabilization. In the case of the Kemp elimination, a general base, Glu L34, carried out the proton abstraction from the isoxazole ring of 5-nitro-benzisoxazole while water molecules delivered specific stabilization at the transition state. The role of water was found to be more pronounced in the allylic isomerization because the solvent actively participated in the stepwise mechanism. A rate-limiting abstraction of the a-proton from the beta,gamma-unsaturated ketone via Glu L34 led to the formation of a neutral dienol intermediate, which was rapidly reprotonated at the gamma-position via a solvent hydronium ion. Preferential channeling of H3O+ in the active site ensured a stereoselective proton exchange from the alpha- to the gamma-position, in good agreement with deuterium exchange NMR and HPLC experiments. Ideas for improved water-mediated catalytic antibody designs are presented. In a technical advancement, improvements to a recent polynomial fitting and integration technique utilizing free energy perturbation theory delivered greater accuracy and speed gains.

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

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Decarboxylation of 6-nitrobenzisoxazole-3-carboxylate in mixed micelles of zwitterionic and positively charged surfactants

The rate of decarboxylation of 6-nitrobenzisoxazole-3-carboxylate, NBOC, was determined in micelles of N-hexadecyl-N,N,N-trimethylammonium bromide or chloride ( CTAB or CTAC), N-hexadecyl-N,N-dimethyl-3-ammonium-1-propanesulfonate (HPS), N-dodecyl-N,N-dimethyl-3-ammonium-1-propanesulfonate (DPS), N-dodecyl-N, N,N-trimethylammonium bromide (DTAB), hexadecylphosphocholine (HPC), and their mixtures. Quantitative analysis of the effect on micelles on the velocity of NBOC decarboxylation allowed the estimation of the rate constants in the micellar pseudophase, k(m), for the pure surfactants and their mixtures. The extent of micellar catalysis for NBOC decarboxylation, expressed as the ratio k(m)/k(w), where k(w) is the rate constant in water, varied from 240 for HPS to 62 for HPC. With HPS or DPS, k(m) decreased linearly with CTAB(C) mole fraction, suggesting ideal mixing. With HPC, k(m) increased to a maximum at a CTAB(C) mole fraction of ca. 0.5 and then decreased at higher CTAB(C). Addition of CTAB(C) to HPC, where the negative charge of the surfactant is close to the hydrophobic core, produces tight ion pairs at the interface and, consequently, decreases interfacial water contents. Interfacial dehydration at the surface in equimolar HPC/CTAB(C) mixtures, and interfacial solubilization site of the substrate, can explain the observed catalytic synergy, since the rate of NBOC decarboxylation increases markedly with the decrease in hydrogen bonding to the carboxylate group.

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

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature. 90-27-7, Name is 2-Phenylbutanoic acid, SMILES is CCC(C1=CC=CC=C1)C(O)=O, in an article , author is SATO, H, once mentioned of 90-27-7, Product Details of 90-27-7.

STUDIES ON URICOSURIC DIURETICS .3. SUBSTITUTED 1,3-DIOXOLO[4,5-F]-1,2-BENZISOXAZOLE-6-CARBOXYLIC ACIDS AND 1,3-DIOXOLO[4,5-G]-1,2-BENZISOXAZOLE-7-CARBOXYLIC ACIDS

A series of substituted 1,3-dioxolo[4,5-f]-1,2-benzisoxazole-6-carboxylic acids 13 and 1,3-dioxolo[4,5-g]-1,2-benzisoxazole-7-carboxylic acids 14 were synthesized and evaluated for diuretic and uricosuric activities in rats. Most of the benzisoxazole derivatives 13 and 14 showed potent diuretic activities. Moderate uricosuric activities were also found in 14a, 14b, and 14f.

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

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Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics, SDS of cas: 90-27-7, 90-27-7, Name is 2-Phenylbutanoic acid, SMILES is CCC(C1=CC=CC=C1)C(O)=O, belongs to Benzisoxazole compound. In a document, author is WANG, GJ, introduce the new discover.

SYNTHESIS AND CATALYTIC PROPERTIES OF CROSS-LINKED HYDROPHOBICALLY ASSOCIATING POLY(ALKYLMETHYLDIALLYLAMMONIUM BROMIDES)

Cross-linked, hydrophobically associating homo- and copolymers were synthesized by free-radical cyclo(co)polymerization of alkylmethyldiallylammonium bromide monomers with a small amount of N,N’-methylenebisacrylamide in aqueous solution using ammonium persulfate as the initiator. The cross-linked homo- and copolymers showed a increase of their reduced viscosity in water and intrinsic viscosity in 1.0 M sodium chloride solutions upon the controlled introduction of crosslinking N,N’-methylenebisacrylamide into their chemical structure. Depending on the hydrophobic group content of the cross-linked copolymers, a conformational transition was revealed by viscosity measurements which is accounted for by intramolecular micelle formation and intermolecular aggregation. The hydrophobic microdomains of the cross-linked polysoaps were characterized by hypsochromic shifts of the long-wavelength absorption band of methyl orange as a solvatochromic probe, noncovalently bound to the macromolecule. Catalysis of the unimolecular decarboxylation of 6-nitrobenzisoxazole-3-carboxylate by the cross-linked copolymers was investigated in aqueous solution at pH 11.3 and 30 degrees C. The cross-linked polysoaps exhibited higher catalytic activities for decarboxylation than the corresponding non-cross-linked copolymer analogues. A maximum in rate constant was found at about 0.2% (w/w) of cross-linking agent in the cross-linked copolymers.

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

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SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF BENZISOXAZOLE DERIVATIVES AND THEIR N-GLUCOSIDES

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

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Studies on the synthetic compatibility of aryloxime linkers in the solid-phase synthesis of 3-aminobenzisoxazoles

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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Cyclisation and decarboxylation in zwitterionic micelles: Effects of head group structure

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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Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. 90-27-7, Name is 2-Phenylbutanoic acid, molecular formula is C10H12O2, belongs to Benzisoxazole compound. In a document, author is Brodie, M. J., introduce the new discover, Quality Control of 2-Phenylbutanoic acid.

Zonisamide: its pharmacology, efficacy and safety in clinical trials

Zonisamide is a benzisoxazole derivative, chemically unrelated to other antiepileptic drugs, that appears to have multiple mechanisms of action, including inhibition of Na+ channels and reduction of T-type Ca2+ currents. It is currently licensed in Europe and the USA for adjunctive treatment of partial seizures in adults, and in Europe as monotherapy for treatment of partial seizures in adults with newly diagnosed epilepsy. Zonisamide displays predictable, dose-dependent pharmacokinetics and has a half-life of similar to 60 h, allowing once- or twice-daily administration. It has a low potential for interactions with other medications, including oral contraceptives. The clinical efficacy of adjunctive zonisamide therapy has been established in four pivotal, phase III, randomized, double-blind, placebo-controlled trials, which together included approximately 850 patients, aged 12-77 years, with refractory partial epilepsy. In all four trials, zonisamide 300-600 mg/day resulted in significant reductions in median total seizure rates vs placebo, and zonisamide was generally well tolerated; the most frequently reported adverse events being somnolence, dizziness and anorexia/weight loss. Subanalysis of the primary European trial indicated that zonisamide was effective when administered as first-line adjunctive treatment, and a long-term extension to the same trial demonstrated that the efficacy and safety/tolerability of adjunctive zonisamide was sustained for up to 36 months. Once-daily monotherapy with zonisamide (200-500 mg/day) has been shown to be non-inferior to, and as well tolerated as, twice-daily monotherapy with controlled-release carbamazepine (400-1200 mg/day) in adults with newly diagnosed partial epilepsy. Zonisamide has also been shown to have favourable long-term retention rates, an important indication of its overall effectiveness.

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

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CHARACTERIZATION OF HUMAN LIVER MICROSOMAL CYTOCHROME-P450 INVOLVED IN THE REDUCTIVE METABOLISM OF ZONISAMIDE

Zonisamide (1,2-benzisoxazole-3-methanesulfonamide) was metabolized to 2-sulfamoylacetylphenol (SMAP) in human liver microsomes under anaerobic conditions. The formation of SMAP was remarkably inhibited by cimetidine, n-octylamine, ketoconazole, and carbon monoxide, indicating that a cytochrome P450 is involved in the metabolism of zonisamide to SMAP in human liver microsomes. The SMAP-producing activity did not correlate with the spectrally determined amount of cytochrome P450. In contrast, the SMAP-producing activity from zonisamide correlated closely with the activity of testosterone 6beta-hydroxylase (r2 = 0.96) and correlated slightly but significantly with the activity of imipramine 2-hydroxylase (r2 = 0.28), but not with those of aniline hydroxylase (r2= 0.09) or benzphetamine N-demethylase (r2= 0.20). In addition, immunoquantitation of cytochrome P450 enzymes in 21 human liver microsomal samples revealed that SMAP formation correlated closely with the amount of P450 3A enzyme and correlated moderately well with that of P450 2D6 but not with that of P450 2C enzyme in human liver microsomes. P450 3A4 exhibited SMAP-producing activity in a reconstituted monooxygenase system. The metabolism of zonisamide to SMAP was almost completely inhibited by anti-P450 3A4 antibody but not by anti-P450 2C9 or anti-P450 2D6 antibodies, suggesting that the amount of P450 3A enzyme may be a major factor influencing the level of metabolism of zonisamide to SMAP in human liver microsomes.

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