Extracurricular laboratory:new discovery of Benzofuran-2-carboxylic acid

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N-(4-(4-(2,3-dichloro- or 2-methoxyphenyl)piperazin-1-yl)butyl) heterobiarylcarboxamides with functionalized linking chains as high affinity and enantioselective D3 receptor antagonists

In the present report, the D3 receptor pharmacophore is modified in the 2,3-diCl- and 2-OCH3-phenyl-piperazine class of compounds with the goal to improve D3 receptor affinity and selectivity. This extension of structure-activity relationships (SAR) has resulted in the identification of the first enantioselective D3 antagonists (R- and S-22) to be reported, wherein enantioselectivity is more pronounced at D3 than at D2, and that a binding region on the second extracellular loop (E2) may play a role in both enantioselectivity and D3 receptor selectivity. Moreover, we have discovered some of the most D3-selective compounds reported to date that show high affinity (Ki) 1 nM) for D3 and ?400-fold selectivity over the D2 receptor subtype. Several of these analogues showed exquisite selectivity for D3 receptors over >60 other receptors, further underscoring their value as in vivo research tools. These lead compounds also have appropriate physical characteristics for in vivo exploration and therefore will be useful in determining how intrinsic activity at D3 receptors tested in vitro is related to behaviors in animal models of addiction and other neuropsychiatric disorders.

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Benzofuran – Wikipedia,
Benzofuran | C8H1913O – PubChem

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Palladium-Catalyzed Tandem Dehydrogenative [4 + 2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations

A palladium-catalyzed tandem dehydrogenative [4 + 2] annulation of terminal olefins with N-sulfonyl amides via C(sp2)-H activation, allylic C(sp3)-H activation, and homoallylic C(sp3)-H elimination processes has been developed. Promoted by the DMSO ligand, various benzamides, heterocyclic arylamides, alkenyl carboxamides, and commercial olefins are found to be efficient substrates to construct important heterocyclic compounds bearing a vinyl substituent with high E stereoselectivity. Using air as the terminal oxidant also provides a great advantage regarding environmental friendliness.

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Benzofuran – Wikipedia,
Benzofuran | C8H1978O – PubChem

Discovery of Benzofuran-2-carboxylic acid

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2-(Arylmethyl)-3-substituted quinuclidines as selective alpha7 nicotinic receptor ligands

A series of 2-(arylmethyl)-3-substituted quinuclidines was developed as alpha7 neuronal nicotinic acetylcholine receptor (nAChR) agonists based on a putative pharmacophore model. The series is highly selective for the alpha7 over other nAChRs (e.g., the alpha4beta2 of the CNS, and the muscle and ganglionic subtypes) and is functionally tunable at alpha7. One member of the series, (+)-N-(1-azabicyclo[2.2.2]oct-3-yl)benzo[b]furan-2-carboxamide (+)-8l), has potent agonistic activity for the alpha7 nAChR (EC50 = 33 nM, Imax = 1.0), at concentrations below those that result in desensitization.

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Benzofuran – Wikipedia,
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Some scientific research about Benzofuran-2-carboxylic acid

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Bisphenol a binds to Ras proteins and competes with guanine nucleotide exchange: Implications for GTPase-selective antagonists

We show for the first time that bisphenol A (10) has the capacity to interact directly with K-Ras and that Rheb weakly binds to bisphenol A (10) and 4,4?-biphenol derivatives. We have characterized these interactions at atomic resolution suggesting that these compounds sterically interfere with the Sos-mediated nucleotide exchange in H- and K-Ras. We show that 4,4?-biphenol (5) selectively inhibits Rheb signaling and induces cell death suggesting that this compound might be a novel candidate for treatment of tuberous sclerosis-mediated tumor growth. Our results propose a new mode of action for bisphenol A (10) that advocates a reduced exposure to this compound in our environment. Our data may lay the foundation for the future design of GTPase-selective antagonists with higher affinity to benefit of the treatment of cancer because K-Ras inhibition is regarded to be a promising strategy with a potential therapeutic window for targeting Sos in Ras-driven tumors.

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Benzofuran – Wikipedia,
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Brief introduction of Benzofuran-2-carboxylic acid

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Investigations of SCIO-469-like compounds for the inhibition of p38 MAP kinase

The p38 MAP kinase is implicated in the release of the pro-inflammatory cytokines TNFalpha and IL-1b. Inhibition of cytokine release may be a useful treatment for inflammatory conditions such as rheumatoid arthritis and Crohn’s disease. A new lead structure for p38 MAP kinase inhibition was identified. Herein, we report the SAR of this new class of p38 inhibitors.

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Top Picks: new discover of Benzofuran-2-carboxylic acid

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A Metal-Free Approach to Carboxylic Acids by Oxidation of Alkyl, Aryl, or Heteroaryl Alkyl Ketones or Arylalkynes

The metal-free oxidation of dialkyl, alkyl aryl, or alkyl heteroaryl ketones or arylalkynes to the corresponding carboxylic acids is achieved using an oxidative mixture of Oxone and trifluoroacetic acid. This green method is a simple and mild protocol to obtain carboxylic derivatives in excellent yields.

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Benzofuran – Wikipedia,
Benzofuran | C8H1726O – PubChem

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One-pot curtius rearrangement processes from carboxylic acids

An efficient and practical synthesis of amine derivatives from carboxylic acids is described using new one-pot Curtius rearrangement processes. The preparation of carbamate-protected amines and anilines, as well as ureas was achieved in good to excellent yields on a multigram scale. Georg Thieme Verlag Stuttgart.

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Benzofuran – Wikipedia,
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A new application about Benzofuran-2-carboxylic acid

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The Generation and Synthetic Utility of Dianions derived from Benzofurancarboxylic Acids

The dianionic species, lithium 2-lithiobenzofuran-3-carboxylate (5) and lithium 3-lithiobenzofuran-2-carboxylate (11b) can be readily generated from the parent acids by reaction with lithium diisopropylamide in tetrahydrofuran at low temperatures.While compound (5) is a useful synthetic intermediate, which reacts efficiently with a number of electrophiles, (11b) instead undergoes rapid opening of the furan ring to give (2-hydroxyphenyl)propynoic acid (10a).By contrast, 5- and 7-methoxybenzofuran-2-carboxylic acids (13a) and (13c) give rise to the dianions (14a) and (14c) which are sufficiently stable at <= -90 deg C to be trapped by aldehydes.The dianion (14b) derived from 6-methoxybenzofuran-2-carboxylic acid (13b), however, suffers rapid ring opening before it can be trapped, even at very low temperatures.A plausible explanation of these observations is given.Metallation of 3-methylbenzofuran-2-carboxylic acid (18) affords the dianion (20), which cannot undergo ring opening and which is a valuable intermediate for the synthesis of a range of 3-substituted benzofuran-2-carboxylic acids. Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Reference of 496-41-3. In my other articles, you can also check out more blogs about 496-41-3

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Archives for Chemistry Experiments of Benzofuran-2-carboxylic acid

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Modifying the N-terminus of polyamides: PyImPyIm has improved sequence specificity over f-ImPyIm

Seven N-terminus modified derivatives of a previously published minor-groove binding polyamide (f-ImPyIm, 1) were synthesized and the biochemical and biophysical chemistry evaluated. These compounds were synthesized with the aim of attaining a higher level of sequence selectivity over f-ImPyIm (1), a previously published strong minor-groove binder. Two compounds possessing a furan or a benzofuran moiety at the N-terminus showed a footprint of 0.5 muM at the cognate ACGCGT site (determined by DNase I footprinting); however, the specificity of these compounds was not improved. In contrast, PyImPyIm (4) produced a footprint of 0.5 muM but showed a superior specificity using the same technique. When evaluated by thermal melting experiments and circular dichroism using ACGCGT and the non-cognate AAATTT sequence, all compounds were shown to bind in the minor-groove of DNA and stabilize the cognate sequence much better than the non-cognate (except for the non-amido-compound that did not bind either sequence, as expected). PyImPyIm (4) was interesting as the DeltaTm for this compound was only 4 C but the footprint was very selective. No binding was observed for this compound with a third DNA (non-cognate, ACCGGT). ITC studies on compound 4 showed exothermic binding with ACGCGT and no heat change was observed for titrating the compound to the other two DNA sequences. The heat capacity (DeltaCp) of the PIPI/ACGCGT complex calculated from the hydrophobic interactions and SASA calculations was comparable to the experimental value obtained from ITC (-146 cal mol-1 K-1). SPR results provided confirmation of the sequence specificity of PyImPyIm (4), with a Keq value determined to be 7.1 ¡Á 106 M-1 for the cognate sequence and no observable binding to AAATTT and ACCGGT. Molecular dynamic simulations affirmed that PyImPyIm (4) binds as a dimer in an overlapped conformation, and it fits snugly in the minor-groove of the ACGCGT oligonucleotide. PyImPyIm (4) is an especially interesting molecule, because although the binding affinity is slightly reduced, the specificity with respect to f-ImPyIm (1) is significantly improved.

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Benzofuran – Wikipedia,
Benzofuran | C8H1749O – PubChem

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Solvent-free synthesis of 2-amino-5-aryloxymenthyl-1,3,4-thiadiazoles and their coumarin or benzofuran bis-heterocyclic derivatives

2-amino-5-aryloxymethyl-1,3,4-thiadiazoles were synthesized rapidly by a microwave-accelerated solvent-free procedure in high yield via the condensation of thiosemicarbazide with aryloxyacetic acids using poly(ethylene glycol)-supported dichlorophosphate as a dehydration reagent. The solvent-free N-acylation of 2-amino-5-aryloxymethyl-1,3,4-thiadiazoles with coumarin-3-carboxylic acid chloride or benzofuran-2-carboxylic acid chloride efficiently afforded corresponding bis-heterocyclic derivatives, 2-(coumarin-3-carboxamido)-5-aryloxymethyl-1,3,4-thiadiazoles, and 2-(benzofuran-2-carboxamido)-5-aryloxymethyl-1,3,4-thiadiazoles. The strategy has advantages of no organic solvent pollution, an elevated reaction rate, an improved yield, and a simple work-up procedure. Copyright Taylor & Francis LLC.

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Benzofuran – Wikipedia,
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