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Thieno[3,2-b]benzofuran – Synthesis and reactions

Thieno[3,2-b]benzofuran was synthesized starling from benzo[b]furan-3(2h)-one or benzo[b]furan-2-carbaldehyde. Electrophilic substitution reactions such as bromination, formylation, acelylation or nitration, take place in position 2. An election donating group in position 2 directs further electrophilic substitution into positions 3 and 6, whereas compounds with an electron acceptor in position 2 are substituted exclusively in position 6. Metallalation with butyllithium took place in position 2. the 1H and 13 C NMR signals of the title compound were fully assigned.

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Benzofuran – Wikipedia,
Benzofuran | C8H1083O – PubChem

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Antitumor agents. 284. new desmosdumotin B analogues with bicyclic B-ring as cytotoxic and antitubulin agents

We previously reported that the biological acti-vity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI50 values of 0.8-2.1 muM. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) overexpressing multidrug resistant cell line. We have now prepared and evaluated 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI50 values of 0.06-0.16 muM, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC50 value of 2.0 muM and colchicine binding by 78% as well as cellular microtubule polymerization and spindle formation.

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Benzofuran – Wikipedia,
Benzofuran | C8H969O – PubChem

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N-heterocyclic carbene catalysed asymmetric cross-benzoin reactions of heteroaromatic aldehydes with trifluoromethyl ketones

A new triazolium salt derived N-heterocyclic carbene catalyses an asymmetric cross-benzoin-type reaction of heteroaromatic aldehydes and various trifluoromethyl ketones in good to excellent yields (69-96%) and moderate to good enantioselectivities (ee = 39-85%). Up to 99% ee can be achieved by recrystallisation.

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Benzofuran – Wikipedia,
Benzofuran | C8H809O – PubChem

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Preparation of 2-arylindole-4-carboxylic amide derivatives

A practical, highly efficient protocol has been developed for the synthesis of functionalized 2-arylindole-4-carboxylic amide derivatives. Commercially available methyl 2-methyl-3-nitrobenzoate gave substituted nitrostyrene benzoic acids by reaction with aromatic aldehydes in the presence of DBU in DMSO. Conversion of these products to the desired amides was followed by Pd-catalyzed reductive cyclization employing carbon monoxide as the terminal reductant to provide the 2-arylindole-4-carboxylic amide derivatives in excellent overall yield for the simple three-step sequence.

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Benzofuran – Wikipedia,
Benzofuran | C8H897O – PubChem

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In Vitro Antitumor Activity of Newly Synthesized Pyridazin-3(2H)-One Derivatives via Apoptosis Induction

Systemic toxicity associated with drug resistance continues to be the major obstacle to curative therapy of cancer. Tumor cell resistance to chemotherapeutic drugs often results in coordinate resistance to other structurally and functionally unrelated drugs and the subsequent development of cross resistance phenotype. Therefore, it seems necessary to identify new molecules as anticancer agents. In this process, we synthesized a series of new pyridazin-3(2H)-one derivatives and evaluated their antitumor potential. These cyclic molecules were synthesized and designed as a combination of benzofuran with pyridazinones. All final compounds have been characterized by spectral and elemental analyses to confirm successful synthesis reactions. To evaluate their anticancer activity, all derivatives were assessed against the human breast adenocarcinoma cell line (MCF-7) and the murine mastocytoma cell line (P815) using the methyl tetrazolium Test (MTT assay). The cytotoxic activity was found to be dose-dependent and the IC50 values of the synthesized compounds ranged from 14.5 to 40 muM against MCF-7 and from 35 to 82.5 muM against P815. At the same time, no cytotoxic activity was observed against normal cells. In order to investigate the molecular mechanism of the most cytotoxic product (6f), apoptosis induction was measured against MCF-7 cells. Using the annexin-V FITC staining technique, we showed that the cytotoxic effect of this product is associated with apoptosis induction.

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Benzofuran – Wikipedia,
Benzofuran | C8H752O – PubChem

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Palladium catalyzed direct 3-arylation of benzofurans using low catalyst loadings

The palladium-catalyzed direct 3-arylation of benzofurans provides a cost-effective and environmentally attractive route for the preparation of 3-arylbenzofuran derivatives. The reactions were carried out using a wide variety of electronically and sterically diverse aryl or heteroaryl bromides with low catalyst loadings. In the presence of only 0.1-0.5 mol% catalyst, products in moderate to good yields were obtained. The aryl bromide reactants were able to tolerate a wide range of functionalities, such as acetyl, propionyl, formyl, ester, nitrile, trifluoromethyl, or fluoro groups. Higher yields were obtained using electron-deficient aryl bromides as reactants compared to using electron-rich aryl bromides. Functionalized benzofuran derivatives, bearing formyl or hydroxymethyl on C2, were also successfully employed.

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Benzofuran – Wikipedia,
Benzofuran | C8H860O – PubChem

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A practical iodine-catalyzed oxidative conversion of aldehydes to nitriles

A simple and efficient method for the direct synthesis of nitriles from aldehydes using ammonium acetate as the nitrogen source has been developed. The reactions were performed with iodine as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant under mild conditions. A variety of aromatic, heteroaromatic, aliphatic and allylic aldehydes could be converted into their corresponding nitriles in good to excellent yields.

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Benzofuran – Wikipedia,
Benzofuran | C8H813O – PubChem

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Gold catalysis: Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond

It takes al-kynes: The formation of furyl-substituted heterocycles from furanynes with donor groups on the furan-alkyne tether and mechanistic control experiments indicate the involvement of open-chained carbenium ions in the overall insertion of an alkyne into a C-C bond, rather than the usual spirocyclic intermediates (see scheme). Copyright

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Benzofuran – Wikipedia,
Benzofuran | C8H842O – PubChem

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Low-Pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes

An efficient and practical protocol for the enantioselective cobalt-catalyzed hydrovinylation of vinylarenes with ethylene at low (1.2 bar) pressure has been developed. As precatalysts, stable [L2CoCl2] complexes are employed that are activated in situ with Et2AlCl. A modular chiral TADDOL-derived phosphine-phosphite ligand was identified that allows the conversion of a broad spectrum of substrates, including heterocyclic vinylarenes and vinylferrocene, to smoothly afford the branched products with up to 99 % ee and virtually complete regioselectivity. Even polar functional groups, such as OH, NH2, CN, and CO2R, are tolerated.

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Benzofuran – Wikipedia,
Benzofuran | C8H962O – PubChem

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Na+-glucose cotransporter inhibitors as antidiabetic agents. II. Synthesis and structure-activity relationships of 4′-dehydroxyphlorizin derivatives

A novel series of 4′-dehydroxyphlorizin derivatives was synthesized and the effects of these compounds on urinary glucose excretion were evaluated in rats. There was a strict structural requirement for activity. Introduction of a small substituent or a fiat ring at the 3- and/or the 4-position on the A ring was permissible, but any change at the bridge part between the A and B rings or in the sugar moiety resulted in complete loss of activity. The 6′- OH group on the B ring was also necessary, and even small structural modifications of the 6′-OH group reduced the activity considerably. Among the compounds synthesized, the 5-benzofuryl derivative 25 was the most potent and was selected as a new lead for further structure-activity relationship investigations.

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Benzofuran – Wikipedia,
Benzofuran | C8H854O – PubChem