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3-Azido-5-(azidomethyl)benzene derivatives are useful compounds for preparing diverse bistriazole compounds and photoaffinity probes for target identification of bioactive compounds. To more easily synthesize a diverse range of diazido compounds, a facile method for synthesizing diazido compounds bearing a transformable functional group, such as iodo, bromo, methoxycarbonyl, or cyano group, was developed. This method is based on formal C-H azidation of 1,3-disubstituted benzenes via regioselective borylation followed by deborylative azidation, with subsequent transformations, such as that of a one-carbon unit on the benzene ring to an azidomethyl group. The functional groups of the diazido compounds were efficiently transformed to various connecting groups, including carboxy, (succinimidyloxy)carbonyl, hydroxymethyl, formyl, bromomethyl, tosylthiomethyl, ethynyl, diazoacetyl, bromoacetyl, boryl, hydroxy, aminocarbonyl, amino, and isothiocyanato groups, leaving the azido groups untouched. Several diazido building blocks were used to prepare diazido compounds by forming amide, thiourea, and sulfide bonds via conjugation at the connecting groups. These results show that the method described here would facilitate diazido probe syntheses and bistriazole library construction.

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

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A small library of structurally diverse alpha-aminophosphonates has been synthesized by reacting alkyl/aryl aldehydes, alkyl/aryl amines and alkyl/aryl phosphites in one-pot catalyzed by Amberlite-IR 120 resin (acidic). All the synthesized a-aminophosphonates were assayed for their in vitro cytotoxic activities against a panel of five human cancer cell lines including A-549, NCI-H23 (Lung), Colo 320DM (Colon), MG-63 (Bone marrow) and Jurkat (Blood T lymphocytes). Compound 4n having (R)-1-phenylethanamine was found to be the most active amongst all the synthesized a-aminophosphonates against all the five cancer cell lines, most prominent being against Jurkat cell line with an IC 50 value of 4 muM. Surprisingly, compound 4o having (S)-1-phenylethanamine was found to be devoid of any cytotoxicity. Our finding suggests that these chemical entities could further serve as interesting template for the design of potential anticancer agents.

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

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A novel series of potent and selective non-peptide neuropeptide Y (NPY) Y1 receptor antagonists, having benzazepine nuclei, have been designed, synthesized, and evaluated for activity. Chemical modification of the R1 and R3 substituents in structure 1 (Chart 1) yields several compounds that show high affinity for the Y1 receptor (K(i) values of less than 10 nM). SAR studies revealed that introduction of an isopropylurea group at R1 and a 3- (benzo-condensed-urea) group, 3-(fluorophenylurea) group, or a 3-(N-(4- hydroxyphenyl)guanidine) group at R3 in structure 1 afforded potent and subtype-selective NPY Y1 receptor antagonists. 3-(3-(Benzothiazol-6- yl)ureido)-1-N-(3-(N’-(3-isopropylureido))benzyl)-2,3,4,5-tetrahydro-1H-1- benzazepin-2-one (21), which was one of the most potent derivatives, competitively inhibited specific [125I]peptide YY (PYY) binding to Y1 receptors in human neuroblastoma SK-N-MC cells (K(i) = 5.1 nM). 21 not only inhibited the Y1 receptor-mediated increase in cytosolic free Ca2+ concentration in SK-N-MC cells but also antagonized the Y1 receptor-mediated inhibitory effect of peptide YY on gastrin-induced histamine release in rat enterochromaffin-like cells. 21 showed no significant affinity in 17 receptor binding assays including Y2, Y4, and Y5 receptors.

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

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Imines react with seven-membered cyclic anhydrides (prepared from the corresponding dicarboxylic acids by a recently discovered in-situ cyclodehydration protocol) by the Castagnoli?Cushman reaction pathway to give privileged seven-membered arene-fused nitrogen-heterocyclic compounds with reagent-controlled diversity of the skeleton and peripheral groups.

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

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Sphingosine kinases (SphK1, SphK2) are main regulators of sphingosine-1-phosphate (S1P), which is a pleiotropic lipid mediator involved in numerous physiological and pathophysiological functions. SphKs are targets for novel anti-cancer and anti-inflammatory agents that can promote cell apoptosis and modulate autoimmune diseases. Herein, we describe the design, synthesis and evaluation of an aminothiazole class of SphK inhibitors. Potent inhibitors have been discovered through a series of modifications using the known SKI-II scaffold to define structure-activity relationships. We identified N-(4-methylthiazol-2-yl)-(2,4?-bithiazol)-2?-amine (24, ST-1803; IC50values: 7.3 muM (SphK1), 6.5 muM (SphK2)) as a promising candidate for further in vivo investigations and structural development.

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

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An efficient synthesis of 2-aryl 4-substituted quinolines from stable and readily available o-cinnamylanilines, prepared from anilines and cinnamylalcohols, has been developed. The reaction occurred via a regioselective 6-endo-trig intramolecular oxidative cyclization using KOtBu as a mediator and DMSO as an oxidant at rt. The reaction showed a broad substrate scope with good to excellent yields.

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

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As part of a program aimed at discovering orally active 2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptor antagonists, we screened our compound library and identified 2-[allyl(4-methylphenyl)amino]-4H-pyrido[3,2-e][1,3]thiazin-4-one (7) as a lead compound that inhibited kainate-induced neurotoxicity mediated by AMPA receptors in rat hippocampal cultures. Structure-activity relationship studies of a series of 2-amino-4H-pyrido[3,2-e][1,3]thiazin-4-one derivatives revealed that substituents on the phenyl ring attached to the 2-amino group and the 4H-pyrido[3,2-e][1,3]thiazin-4-one ring system play an important role in inhibitory activity against kainate-induced neurotoxicity. Several analogs bearing a phenyl group with a 4-substituent or five- or six-membered ring fused at the 3,4-positions exhibited potent inhibitory activity against kainate-induced neurotoxicity. Further, some of these compounds exhibited significant suppression of maximal electroshock seizure in mice following oral administration. Of these compounds, 2-[(4-chlorophenyl)(methyl)amino]-4H-pyrido[3,2-e][1,3]thiazin-4-one (16i) (YM928) demonstrated the most potent inhibitory effect with an ED50 value of 7.4 mg/kg.

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

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Four new organic photosensitizers (SH-11?14) that introduced methoxy groups as an additional donor were synthesized, and used in dye-sensitized solar cells. The dyes were designed in order to investigate the effects on the dye photophysical properties and the cell photovoltaic performance, by the number, position, and shape of methoxy groups introduced at the para-/ortho- and para-/meta- and para-(open or closed ring shape) positions on the triphenylamine donor. The introduction of methoxy groups led to bathochromic shift of the absorption spectrum, and enhancement of the molar extinction coefficient of the dyes. Their introduction decreased the amount of dye adsorbed on TiO2surface, due to the increased steric hindrance. As their number increased, an open-circuit voltage value decreased. All things considered, the dye (SH-14) with closed ring shape shows the best conversion efficiency of 6.01% under AM 1.5G conditions (N719 dye’s 7.59% under the same conditions).

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

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Reactions catalyzed interfaces commonly occur at high coverage and in condensed media, causing turnover rates to depend on composition, collectively referred to as solvent effects. In a patent,Which mentioned a new discovery about Application In Synthesis of 2,3-Dihydrobenzo[b][1,4]dioxin-6-amine, Application In Synthesis of 2,3-Dihydrobenzo[b][1,4]dioxin-6-amine

The reaction of arylglyoxals, 4-hydroxycoumarin, and aromatic amines such as 7-amino-2-methylchromone, 6/7-aminoflavone, 7-amino-4-methylcoumarin, 1-amino-9-fluorenone, 1-aminoanthraquinone and aniline derivatives in acetic acid medium under microwave conditions provides the corresponding regioselective fused pyrroles having hydroxycoumarin and aryl substituents. Alternatively, we have developed another method using in situ arylglyoxals from acetophenone derivatives by I2/DMSO promoted C-H oxidation followed by one-pot three component cyclization reactions to provide similar fused pyrroles. Using both the methods a series of novel pyrroles fused with pharmacologically important chromone, flavone, coumarin, fluorenone, and anthraquinone moieties were synthesized under metal-free reaction conditions in good to very good yields within a short reaction time. The structures of the synthesized fused pyrroles have been unambiguously confirmed by spectroscopic techniques, mass analysis and single crystal XRD.

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

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Synthetic Route of 22013-33-8, Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption.In a document type is Patent, and a compound is mentioned, 22013-33-8, Name is 2,3-Dihydrobenzo[b][1,4]dioxin-6-amine, introducing its new discovery.

The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.

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