28-Sep News Final Thoughts on Chemistry for C6H12O3

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Cytokinin-like activity of N ‘-substituted N-phenylureas

We have synthesized 14 N-phenylurea derivatives, differing in the heterocyclic portion linked in N’-position, and tested their cytokinin-like activity. Three different bioassays were used: the chlorophyll level determination test, the bioassay for the expression of hormone-induced chimeric Pg5-GUS gene and the tomato regeneration test, in which 1,2-benzisoxazole-3-acetic acid (BOAA) was utilized as auxin. The cytokinin-like activity showed by three of these compounds in the regeneration assay seems to be related to their different heterocyclic nature. Results obtained indicate that the N-phenyl-N’-1,3,4-thiadiazol-2-ylurea (compound 4), an isomer of N-phenyl-N’- 1,2,3-thiadiazol-5-ylurea (thidiazuron, TDZ), in the absence of auxin induces shoot regeneration in the 34,2% of the explants cultured; the N-plienyl-N’-(3-chloro-1,2-benzisothiazol-7-yl) urea (compound 10), structurally different from TDZ, in the absence of auxin induces shoot regeneration in the 25,9% of explants, significantly lower than that of TDZ (68,8%). N-phenyl-N’-benzothiazol-6-ylurea (compound 13), structurally different from TDZ, in the absence of auxin induces the 99,5% of shoot regeneration, significantly different from that of the other substances. The addition of auxin in the cotyledon regeneration assay reduces the differences. The compound 13 could be considered a new phenylurea derivative with a highly specific cytokinin-like activity.

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

26-Sep-21 News Decrypt The Mystery Of C6H12O3

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Reactivity of Lithium beta-Ketocarboxylates: The Role of Lithium Salts

Lithium beta-ketocarboxylates 1(COOLi), prepared by the reaction of lithium enolates 2(Li+) with carbon dioxide, readily undergo decarboxylative disproportionation in THF solution unless in the presence of lithium salts, in which case they are indefinitely stable at room temperature in inert atmosphere. The availability of stable THF solutions of lithium beta-ketocarboxylates 1(COOLi) in the absence of carbon dioxide allowed reactions to take place with nitrogen bases and alkyl halides 3 to give alpha-alkyl ketones 1(R) after acidic hydrolysis. The sequence thus represents the use of carbon dioxide as a removable directing group for the selective monoalkylation of lithium enolates 2(Li+). The roles of lithium salts in preventing the disproportionation of lithium beta-ketocarboxylates 1(COOLi) and in determining the course of the reaction with bases and alkyl halides 3 are discussed.

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

09/24/21 News What I Wish Everyone Knew About C6H12O3

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Chemical Research Letters, May 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. In an article, author is Deng, BL, once mentioned the application of 1191-25-9, Name is 6-Hydroxyhexanoic acid, molecular formula is C6H12O3, molecular weight is 132.1577, MDL number is MFCD00046560, category is benzisoxazole. Now introduce a scientific discovery about this category, Synthetic Route of 1191-25-9.

Synthesis and anti-HIV activity of new alkenyldiarylmethane (ADAM) non-nucleoside reverse transcriptase inhibitors (NNRTIs) incorporating benzoxazolone and benzisoxazole rings

The HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) constitute a large and structurally diverse set of compounds, several of which are currently used in the treatment of AIDS. A series of novel alkenyldiarylmethanes (ADAMs) were designed and synthesized as part of an ongoing investigation to replace the metabolically labile methyl ester moieties found in the ADAM pharmacophore with stable modifications that retain the potent anti-HIV activity of the parent compounds. Unsurprisingly, the rat plasma half-lives of the new ADAMs were not improved when compared to the parent compounds, but all of the synthesized ADAMs inhibited the cytopathic effect of HIV-1 in cell culture. The most potent compound identified was (E)-5-[1-(3,7-dimethyl-2oxo-2,3-dihydro-benzoxazol-5-yl)-5-methoxycarbonyl-pent-1-enyl]-2-methoxy-3-methylbenzoic acid methyl ester (7), which inhibited the cytopathic effects of both HIV-1(RF) and HIV-1(IIIB) strains in cell cultures with EC50 values of 30 and 90 nM, respectively, and inhibited HIV-1 reverse transcriptase with an IC50 of 20 nM. (c) 2005 Elsevier Ltd. All rights reserved.

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

9/16/21 News Discover the magic of the C6H12O3

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Chemical Research Letters, May 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. In an article, author is Chicha, Hakima, once mentioned the application of 1191-25-9, Name is 6-Hydroxyhexanoic acid, molecular formula is C6H12O3, molecular weight is 132.1577, MDL number is MFCD00046560, category is benzisoxazole. Now introduce a scientific discovery about this category, Name: 6-Hydroxyhexanoic acid.

Reduction of 3-nitrophthalic anhydride by SnCl2 in different alcohols: a simple synthesis of alkyl 1,3-dihydro-3-oxo-2,1-benzisoxazole-4-carboxylates

A new, mild and efficient process is developed for the synthesis of alkyl 1,3-dihydro-3-oxo-2,1-benzisoxazole-4-carboxylates through the reduction of 3-nitrophthalic anhydride by SnCl2 in different alcohols. The synthesis of benzisoxazoles bearing a sulfonamide functionality is also reported. The structure of sulfonamide 8d is confirmed by X-ray diffraction analysis. (c) 2013 Elsevier Ltd. All rights reserved.

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

13 Sep 2021 News Downstream Synthetic Route Of C6H12O3

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Reaction of 1-nitro-4-(1,2,3-triazolyl/tetrazolyl)benzenes with arylacetonitriles in an alcoholic medium in the presence of excess alkali gives novel 2,1-benzisoxazoles. These findings indicate a high reactivity of nitroarenes activated by the azole ring due to their electron-deficient character. Moreover, it was found that annulation of the isoxazole ring occurred regioselectively in disubstituted nitroarenes. In the case of 1-(4-nitrophenyl)-1H-tetrazole, the tetrazole ring cleaved faster than the sigma(H)-adduct was formed.

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Benzisoxazole – Wikipedia,
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10-Sep-2021 News More research is needed about C6H12O3

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Under electron ionization conditions, the ortho-substituted Schiff bases N-benzylidene-o-toluidine (1a), N-(o-methylbenzylidene)aniline (1b), N-salicylideneaniline (1c) and N-(o-methoxybenzylidene)aniline (1d) give fragment ions which have been shown by collision-activated mass-analysed ion kinetic energy spectra to have the structure of the protonated molecular ions of indole (2), benzofuran (3), and 1,2-benzisoxazole (4). The molecular ion of N-(o-methylbenzylidene)-o-toluidine (1f) gives as fragment ions not only the protonated molecular ion (2) of indole and the tropylium ion but also the molecular ion of anthracene. Attempts to find supporting evidence for a mechanism for this rearrangement by deuterium labelling of a methyl group in (1b), such as (1g), have been unsuccessful.

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

7 Sep 2021 News Chemistry Milestones Of C6H12O3

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A simple and efficient method for the synthesis of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride is achieved. This reaction involves hydroxylamine sulfate/KOH mediated, in situ generated oxime formation and its subsequent internal cyclisation followed by alkaline hydrolysis of N-protected ketone in one step. Synthesis of 1,2-benzisoxazole analogues is described and they are found to be potent acetylcholinesterase inhibitors.

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Reference:
Benzisoxazole – Wikipedia,
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3 Sep 2021 News Why Are Children Getting Addicted To C6H12O3

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In this study, we compared the anticonvulsive effects of zonisamide (ZNS) with those of phenytoin (PHT), carbamazepine (CBZ) and phenobarbital (PB) in amygdaloid (AM)-kindled rats. Electrodes were implanted into the left AM of adult male Wistar rats. The animals were kindled at the afterdischarge (AD) threshold. After the completion of kindling, the generalized seizure triggering threshold was determined. The drugs were administered intraperitoneally in animals that showed stable generalized convulsions at near-threshold stimulation. Immediately after each drug trial, venous blood was sampled and the serum drug concentration was measured using EMIT or HPLC. All the drugs suppressed secondary generalization at lower doses, and further regressed the seizure stage and reduced the AD duration at higher doses. Higher doses of all drugs except ZNS, however, produced motor ataxia or lethargy. Thus, ZNS seemed to have a wider therapeutic range than other conventional antiepileptic drugs. An additional experiment on the effects of ZNS against supra-threshold stimulation suggested that a major action of ZNS in the kindling model is to attenuate the seizure spread rather than to elevate the AD threshold at the focus.

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

Extended knowledge of C6H12O3

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Although possible usefulness of non-selective monoamine oxidase (MAO) inhibitors for Parkinson’s disease therapy has been suggested in the literature, MAO inhibitors whose inhibition is reversible and have dual action to both MAO-A and -B subtypes is not available yet. Subtype selectivity and reversibility of a series of novel MAO inhibitors, 3-(2-aminoethoxy)-1,2-benzisoxazole derivatives, were studied. Several dual MAO inhibitors, which inhibit both MAO-A and -B, were obtained. When administered to mice, their effects were generally reversible. Among the derivatives, RS-1636 and RS-1653 had much longer duration of brain MAO-B inhibition than that of MAO-A. In vitro, the inhibited MAO-A activity by these compounds was partially recovered by buffer change at 4degreesC, while little MAO-B activity was recovered. Although it is not fully elucidated yet, the reversibility of these inhibitors is probably determined primarily by this dissociation profile. This unique differential reversibility indicates that optimization of the balance of actions can be achieved by differentiating reversibility to each target molecule.

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

Why Are Children Getting Addicted To C6H12O3

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Chemical Research Letters, May 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. In an article, author is Searcey, M, once mentioned the application of 1191-25-9, Name is 6-Hydroxyhexanoic acid, molecular formula is C6H12O3, molecular weight is 132.1577, MDL number is MFCD00046560, category is benzisoxazole. Now introduce a scientific discovery about this category, Application In Synthesis of 6-Hydroxyhexanoic acid.

-2-Hydroxybenzaldoximes are reduced under mild conditions of ammonium formate/Pd-C in methanol to give secondary amines. Benzisoxazoles react under the same mild conditions to give the same products. A possible mechanism is suggested, involving the intermediacy of the benzisoxazole in the oxime conversion. (C) 2003 Elsevier Ltd. All rights reserved.

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