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Aurones and auronols are naturally occurring 2-benzylidenebenzof-uranone- 3(2H)-one derivatives. Aurones have a limited occurrence in fruits, vegetables, and bright yellow color to flowers such as cosmos and coreopsis. Aurones possess a wide range of biological activities, such as antitumor, antifungal, phytoalexin, and so on. Some aurone derivatives have been studied as antitumor drug molecules, but 2-benzylidene-5-bromobenzofuranone-3(2H)-one series have not been reported yet. In this paper, we’d like to report the design, synthesis, and biological evaluation of the novel aurone derivatives. All the newly synthesized compounds were characterized by 1H NMR and their antitumor activities were evaluated by using MTT method in HT-29, K562, and HepG2 cell lines. 5-bromo-2-(4-nitrobenzylidene) benzofuran-3(2H)-one demonstrated good antitumor activity against K562 cells with an IC50 of 0.37 lM. Springer-Verlag Berlin Heidelberg 2014.

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Benzofuran – Wikipedia,
Benzofuran | C8H3616O – PubChem

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Death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet beta-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried out a high throughput screening and identified compound 4 as a moderate DRAK2 inhibitor with an IC50value of 3.15 muM. Subsequent SAR studies of hit compound 4 led to the development of novel benzofuran-3(2H)-one series of DRAK2 inhibitors with improved potency and favorable selectivity profiles against 26 selected kinases. Importantly, most potent compounds 40 (IC50 = 0.33 muM) and 41 (IC50 = 0.25 muM) were found to protect islet beta-cells from apoptosis in dose-dependent manners. These data support the notion that small molecule inhibitors of DRAK2 represents a promising strategy for the treatment of diabetes.

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Aurones are a small subclass of the flavonoid family known primarily for their unusual structure and the golden yellow color they impart to the flowers of snapdragons and cosmos. Most studies of aurones focus on their range of biological activities, but relatively little has been reported with respect to their optical properties, unlike their aza and thio analogs. What little is known has focused entirely on the influence of the benzylidene portion. In this study, the influence of substitution in the benzofuranone ring on the UV-vis spectrum is explored, as well as an initial screening of their toxicity and a qualitative preliminary study of their potential to act as fabric dyes.

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Benzofuran – Wikipedia,
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H3PW12O40 · xH2O efficiently catalyzes the one-pot pseudo three-component reaction of benzofuran- 3(2H)-ones and various alcohols to afford the corresponding bibenzofuran derivatives with various alkoxy groups in 3-position.

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The 5HT1 receptor agonist GR1510048 (2b), labelled with carbon-14 at C-3 of the benzofuran ring, was prepared in 19% overall yield in five steps from 5-bromo-2-methoxybenzoic [14C]acid (3b).

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We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of alpha,beta-unsaturated benzofuran-3(2H)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).

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Compounds in a structurally novel series of substituted 10H-benzo[4,5]furo[3,2-b]indole-1-carboxylic acids and related 5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acids were prepared and shown to possess potent, bladder-selective smooth muscle relaxant properties and thus are potentially useful for the treatment of urge urinary incontinence. Electrophysiological studies using rat detrusor myocytes have demonstrated that prototype compound 7 produces a significant increase in hyperpolarizing current, which is iberiotoxin (IbTx)-reversed, thus consistent with activation of the large-conductance Ca2+-activated potassium channel (BKCa).

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Compounds such as those represented by Formulas 1-6 can be used in topical liquids, creams, or other dosage forms such as solids, for reducing intraocular pressure, treating glaucoma, growing hair, or other medical uses.

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A class of substituted azetidine, pyrrolidine and piperidine derivatives of Formula I are selective agonists of 5-HT 1 -like receptors, being potent agonists of the human 5-HT 1Dalpha receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT 1Dalpha receptor subtype relative to the 5-HT 1Dbeta subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT 1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT 1D receptor agonists. STR1

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Benzofuran – Wikipedia,
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Described herein is an asymmetric allylic aromatization (AAAr) strategy that employs readily accessible equivalents of benzylic nucleophiles in iridium-catalyzed allylic substitution reactions with the concomitant formation of aromatic rings by aromatization. The optimized reaction conditions involving a catalyst derived from a commercially available iridium precursor and the Carreira ligand are compatible with equivalents of benzylic nucleophiles derived from 4- or 5-methyloxazoles, 5-methylthiazoles, 4- or 5-methylfurans, 2- or 3-methylbenzofurans, 3-methylbenzothiophene, 3-methylindole, 1-methylnaphthalene, and methylbenzene. This strategy provides straightforward accesses to valuable heterocyclic aromatic compounds, bearing a homobenzylic stereogenic center, in an enantiopure form and would be difficult to access otherwise. The versatility of the reaction was showcased by the further elaboration of the products into useful building blocks and a drug analogue.

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Benzofuran – Wikipedia,
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