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A new one-pot palladium-catalyzed process between N-tosylhydrazones, N-(dihalophenyl)-imidates, and amines was designed. This reaction involves Barluenga cross-coupling and N-arylation followed by cyclization to produce functionalized benzimidazoles. During this transformation, one C=C bond and two C=N bonds were created by a single palladium-catalyzed reaction. Depending on the starting materials, a library of 5-(1-arylvinyl)-1H-benzimidazoles was synthesized. Among several arylvinylbenzimidazole derivatives evaluated, one compound exhibits excellent antiproliferative activity in the nanomolar concentration range against human colon carcinoma cell lines (HCT-116) and human lung adenocarcinoma epithelial cell lines (A549).

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

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Studies on the discovery of tyrosinase enzyme inhibitors and exploration for better cytotoxic agents remain an important line in drug discovery and development. A series of synthetic chalcones and pyrazoline derivatives was evaluated for their inhibitory effects on the diphenolase activity of mushroom tyrosinase. The effects of these compounds on proliferation and microtubule assembly were also evaluated in seven different cancer cell lines. The results revealed that some of the synthetic compounds showed significant inhibitory activity, with four compounds being more potent tyrosinase inhibitors than the reference standard inhibitor kojic acid. Several compounds were toxic to cancer cell lines. Compound 1a was found to possess the highest anticancer activity towards all cell lines with an IC50 in the range of 0.9-2.2 muM. Seven of the compounds showed considerable tubulin polymerization activity at a concentration of 25 muM. Molecular modeling studies of these synthetic compounds were performed to investigate their interactions with the tyrosinase enzyme. The structure-activity relationship (SAR) study using in-silico analysis matched well with the in vitro tumour cell inhibitory activity.

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

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Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. In a patent, 2879-20-1, name is 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone, introducing its new discovery. SDS of cas: 2879-20-1

6-Cyclopropyl- and 6-(1-methylcyclopropyl)-1,4-benzodioxanes have been synthesized as the first cyclopropyl-1,4-benzodioxanes.It was shown that nitration of these compounds occurs with retention of the three carbon ring.In contrast to simple ethers of cyclopropylphenols, nitration leads only to 7-nitro-6-cyclopropyl- and 7-nitro-6-(1-methylcyclopropyl)-1,4-benzodioxanes, respectively.Nitration of 7-nitro-6-cyclopropyl-1,4-benzodioxane occurs regioselectively to give exclusively the 7,8-dinitro product.The structure of the nitration products was confirmed by their rearrangement to the corresponding nitrosopropionyl-1,4-benzodioxanes.

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

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A molecular iodine-mediated formal [2+1+1+1] cycloaddition for the efficient synthesis of pyrrolo[2,1-a]isoquinolines from acetophenones, 1,2,3,4-tetrahydroisoquinoline (THIQ) and DMSO has been developed. Mechanistic studies revealed that DMSO served as the methylene source, and this novel protocol involves intermolecular cycloaddition of two in situ generated intermediates that enable efficient formation of one C-N bond and three C-C bonds via multiple sequential C-H functionalizations.

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

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When the N,N-dialkylacetamide side chain of the highly ET(A)-selective endothelin antagonist ABT-627 (1; [2R,3R,4S]-2-(4-methoxyphenyl)-4-(1,3- benzodioxol-5-yl)-1-[[(N,N-dibutylamino)carbonyl]methyl]pyrrolidine-3- carboxylic acid; A-147627) is replaced by N,S-dialkylsulfonami-doethyl, the resultant analogs retain ET(A) affinity, but exhibit substantial ET(B) affinity as well. Structure-activity studies reveal that modifications in the length of the two alkyl groups, and in the substitution on the anisyl ring, are important in optimizing this ‘balanced’ antagonist profile. In particular the combination of an N-n-propyl group, an S-alkyl chain between four and six carbons in length, and a fluorine atom ortho to the aromatic OCH3 provides compounds with sub-nanomolar affinities for both receptor subtypes, and with ET(A)/ET(B) ratios close to 1. A number of these compounds also exhibit oral bioavailabilities (in rats) in the 30-50% range and have substantial plasma half-lives. The balanced receptor-binding profile of these potent and orally bioavailable compounds complements the ET(A) selectivity observed with 1.

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

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Employing simple and readily available aromatic ketones and anilines as starting materials resulted in the construction of 2-acylbenzothiazoles via a novel self-sequence reaction network, which assembles six reactions in one pot. The reaction network not only supplied a novel method for constructing complex molecules but also provided a typical example for logical self-organization synthesis.

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

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A facile method has been suggested for constructing pyrrolo[4,3,2-de]quinolinones by addition of acetophenones to 4-nitroisatin followed by reduction of the nitro group and spontaneous cyclisation.

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

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Catalytic reductions of carbonyl-containing compounds are highly important for the safe, sustainable, and economical production of alcohols. Herein, we report on the efficient transfer hydrogenation of ketones catalyzed by a highly potent Mn(I)?NHC complex. Mn?NHC 1 is practical at metal concentrations as low as 75 ppm, thus approaching loadings more conventionally reserved for noble metal based systems. With these low Mn concentrations, catalyst deactivation is found to be highly temperature dependent and becomes especially prominent at increased reaction temperature. Ultimately, understanding of deactivation pathways could help close the activity/stability-gap with Ru and Ir catalysts towards the practical implementation of sustainable earth-abundant Mn-complexes.

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

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An experimental protocol to achieve the Meerwein-Ponndorf-Verley (MPV) reduction of ketones under mildly basic conditions is reported. The transformation is tolerant of a range of ketone substrates, including O- and S-containing heterocycles, is scalable, and shows potential to be used as a platform to access enantioenriched products. These studies provide a general method for achieving the reduction of ketones under mildly basic conditions and offer an alternative protocol to more well-known Al-based MPV reduction conditions.

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

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Related Products of 2879-20-1, Chemical Research Letters, May 2021. The appropriate choice of redox mediator can avoid electrode passivation and overpotential, which strongly inhibit the efficient activation of substrates in electrolysis. 2879-20-1, Name is 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone,introducing its new discovery.

The novel reaction system comprising air/NH4NO3(cat.)/I2/H2SO4(cat.)is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative alpha-iodination of aryl, heteroaryl, alkyl, and cycloalkyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved.

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