Discovery of 2,3-Dihydrobenzo[b][1,4]dioxin-6-amine

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Anaplastic lymphoma kinase (ALK) is a receptor tyrosine kinase responsible for development of various tumor types. In this study, we synthesized a series of novel 2,4-diarylaminopyrimidine derivatives possessing a unique N-(3-pyridinylmethyl)urea moiety as ALK inhibitors. The most promising analog 5m bearing a 3-methoxy-4-morpholinophenyl substituent significantly inhibited proliferation of ALK positive H3122 and Karpas-299 cells with IC50 values about 10 nM, which were comparable with positive control LDK378. Compound 5m suppressed phosphorylation of ALK and its downstream proteins, and showed low cytotoxicity on normal human primary fibroblast cells (BJ cells). The binding mode of 5m was proposed by docking simulation, which explains the important role of N-(3-pyridinylmethyl)urea moiety. Furthermore, compound 5m exhibited favorable liver microsomal stability and significant efficacy in H3122 xenograft mice model. Interestingly, compound 5m also showed broader anti-proliferative activity on other human tumor cell lines, which was different from other ALK inhibitors.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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We have synthesized quinolinones with potential antiparasitic and anti-HIV activities by an original two-step method involving microwave irradiation and have evaluated their activities against Plasmodium falciparum, Leishmania donovani, Trichomonas vaginalis, and HIV. None of the tested compounds had been previously described using this method of synthesis. One of the compounds had interesting antiparasitic and anti-HIV activity, which could be improved by substitution with different radicals.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. Recommanded Product: 2,3-Dihydrobenzo[b][1,4]dioxin-6-amine, 22013-33-8, name is 2,3-Dihydrobenzo[b][1,4]dioxin-6-amine. In an article,Which mentioned a new discovery about 22013-33-8

The present research work involved the reaction of 2,3-dihydro-1,4-benzodioxin-6-amine (1) and benzenesulfonyl chloride (2) under dynamic pH control at 10 using aqueous Na2CO3. This reaction yielded 2,3-dihydro-1,4-benzodioxin-6-yl)benzenesulfonamide (3), which was further substituted at N-position with various alkyl/aryl halides (4a ? 4m) in N,N-dimethylformamide and catalytic amount of lithium hydride to obtain N-substituted (2,3-dihydro-1,4-benzodioxin-6-yl)benzenesulfonamides (5a ? 5m). The projected structures of the synthesized derivatives were confirmed using various spectral techniques (IR, 1H NMR and EIMS). The synthesized derivatives were screened for antibacterial potential and inhibitory activity against lipoxygenase enzyme.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

Final Thoughts on Chemistry for C9H8O4

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Two series of novel 2,3-dihydrobenzo[b][1,4]dioxin-containing 4,5-dihydro-1H-pyrazole derivatives C1-C15 and D1-D15 have been synthesized and evaluated for their B-Raf inhibitory and anti-proliferation activities. Compound C14 ((3-(4-bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3- dihydrobenzo[b][1,4]dioxin-6-yl)methanone) showed the most potent biological activity against B-RafV600E (IC50 = 0.11 muM) and WM266.4 human melanoma cell line (GI50 = 0.58 muM), being comparable with the positive control Erlotinib and more potent than our previous best compound, while D10 ((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(5-(3- fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone) performed the best in the D series (IC50 = 1.70 muM; GI50 = 1.45 muM). The docking simulation was performed to analyze the probable binding models and poses and the QSAR model was built for reasonable design of B-Raf inhibitors in future. The introduction of 2,3-dihydrobenzo[b][1,4]dioxin structure reinforced the combination of our compounds and the receptor, resulting in progress of bioactivity.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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We’ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 22013-33-8, and how the biochemistry of the body works.Computed Properties of C8H9NO2

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The aim of the present research work was to investigate the enzyme inhibitory potential of some new sulfonamides having benzodioxane and acetamide moieties. The synthesis was started by the reaction of N-2,3-dihydrobenzo[1,4]-dioxin-6-amine (1) with 4-methylbenzenesulfonyl chloride (2) in the presence of 10% aqueous Na2CO3 to yield N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-methylbenzenesulfonamide (3), which was then reacted with 2-bromo-N-(un/substituted-phenyl)acetamides (6a-l) in DMF and lithium hydride as a base to afford various 2-{2,3-dihydro-1,4-benzodioxin-6-yl[(4-methylphenyl)sulfonyl] amino}-N-(un/substituted-phenyl)acetamides (7a-l). All the synthesized compounds were characterized by their IR and 1H-NMR spectral data along with CHN analysis data. The enzyme inhibitory activities of these compounds were tested against a-glucosidase and acetylcholinesterase (AChE). Most of the compounds exhibited substantial inhibitory activity against yeast a-glucosidase and weak against AChE. The in silico molecular docking results were also consistent with in vitro enzyme inhibition data.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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The 5-alkyl-2-dimethylamino-1,3-dithiolium-4-thiolate mesoion could be umpoled with sulfuryl chloride to yield a dicationic electrophile 3 that reacted with various electron-rich aromatic substrates to yield arylthio-substituted 1,3-dithiolium salts 13-25. Two of these compounds have been transformed to the corresponding symmetrical tetrathiafulvalenes 43 and 44, and their cyclovoltammetric behaviour recorded. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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A general method for the regioselective solvent free Friedel-Crafts acylation of 2-substituted-1,4-benzodioxin derivatives in excellent yields employing the AlCl3-DMA reagent with acyl halides or anhydrides as acylating agents is described. The acylation of 2-substituted-1,4-benzodioxin derivatives provides the 6-acyl compound as the major product. However, the saturated analogs affords the 7-acyl regioisomer as the main compound.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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hemistry is a science major with cience and engineering. The main research directions are chemical synthesis, preparation and modification of special coatings, and research on the structure and performance of functional materials , Computed Properties of C8H9NO2. Introducing a new discovery about 22013-33-8, Name is 2,3-Dihydrobenzo[b][1,4]dioxin-6-amine

A simple and straightforward method for facile access to coumarin-fused dihydroquinolines (4) has been developed using the microwave-assisted multicomponent reactions of 4-hydroxycoumarin, aldehydes and aromatic amines in water catalyzed by bismuth triflate. Under solvent-free and conventional heating conditions, the same combination provided the corresponding coumarin-fused quinolines (5). An alternative and rapid method for the conversion of (4) to (5) with very good yields was also developed using N-bromosuccinamide. Single-crystal X-ray crystallographic analysis of one of the products (4q) showed that the products are regioselective and that the reactions proceed via 1,2-addition followed by 6pi-electrocyclization instead of a Skraup-Doebner-von Miller type reaction. Substituted quinoline carboxylic acid derivatives (7) were synthesized selectively from (4) by ring opening of the coumarin moiety followed by aromatization using NaOH/DMSO under reflux conditions. Considering the presence of the polycyclic conjugated structure of the synthesized compounds 4 and 5 with the coumarin moiety, preliminary photophysical studies were carried out and promising quantum yields were observed along with a maximum quantum yield (of = 0.65) for 4j.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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The first KI-catalyzed direct acyloxylation of indolin-3-ones with carboxylic acids has been developed using 30% aq. H2O2 as a green oxidant at room temperature. Through this strategy, various C2-acyloxy indolin-3-ones were obtained in up to 96% yield. Moreover, the C2-acyloxy indolin-3-ones can serve as versatile intermediates for the synthesis of nucleophilic 2-monoarylated indolin-3-ones and 3-ylidene indoles.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Pyrrolo[1,2-a]quinoxalines were synthesized through a three-component reaction of 2-alkoxy-2,3-dihydrofuran, o-phenylenediamine and ketone. This reaction was performed in nitromethane by using boron trifluoride etherate as catalyst. Mechanism of this reaction involves the following two steps: (i) a condensation reaction of the dihydrofuran with o-phenylenediamine, which produced a N-(2-aminophenyl)pyrrole derivative that can act as a 1,5-bisnucleophile, and (ii) an intramolecular Mannich-type reaction of the bisnucleophile and ketone to produce the pyrrolo[1,2-a]quinoxaline derivative.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem