Category: 17403-47-3

Gu, Ling-Hui et al. published their research in Tetrahedron in 2014 | CAS: 17403-47-3

5-Nitro-2,3-dihydrobenzofuran (cas: 17403-47-3) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.Application In Synthesis of 5-Nitro-2,3-dihydrobenzofuran

A mild and efficient amidation of cyclic ethers catalyzed by rhodium caprylate was written by Gu, Ling-Hui;Zhang, Dan-Dan;Qi, Qing-Rong;Yin, Ping;He, Ling. And the article was included in Tetrahedron in 2014.Application In Synthesis of 5-Nitro-2,3-dihydrobenzofuran This article mentions the following:

A small quantity of Rh2(O2CC7H15)4 catalyzed the α-amidation of cyclic ethers under mild conditions, in the presence of electron-withdrawing p-chlorobenzenesulfonamide/PhI(OAc)2 as the nitrene source, in CH2Cl2. The corresponding N-substituted amino cyclic ethers were successfully obtained in good yields, e.g., I, and compatibility with other oxidant sensitive structures in one-pot reaction. In the experiment, the researchers used many compounds, for example, 5-Nitro-2,3-dihydrobenzofuran (cas: 17403-47-3Application In Synthesis of 5-Nitro-2,3-dihydrobenzofuran).

5-Nitro-2,3-dihydrobenzofuran (cas: 17403-47-3) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.Application In Synthesis of 5-Nitro-2,3-dihydrobenzofuran

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

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In heterogeneous catalysis, the catalyst is in a different phase from the reactants. Computed Properties of C8H7NO3, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 17403-47-3, name is 5-Nitro-2,3-dihydrobenzofuran. In an article，Which mentioned a new discovery about 17403-47-3

Because they are a potential source of valuable structural information, experimental and theoretical results are reported for the bond-order, conformational, and substituent dependencies of the long range H – H coupling constants over four bonds (orthobenzylic coupling, Job) between protons on an sp3-hybridized alpha-carbon atom and the ortho protons of aromatic systems.A large number of methyl aromatic systems were synthesized and their coupling constants were accurately measured.The best correlations in this series of compounds were with the square of the mobile ?-bond order and with the mutual atom-atom polarizability ?rhorho’.In addition, several series of compounds with defined geometries and a range of dihedral angles were synthesized and the 1H NMR parameters were measured.The best agreement of the data is with a semiempirical equation, which relates the orthobenzylic coupling constant to ?rhorho’ and to dihedral angles according to the equation Job(phi, ?rhorho’) = 6.90 ?rhorho’ sin2phi – 0.32 cos2phi Hz.Substituent effects on Job are not usually important; exceptions are found in the 1-substituted acenaphthene derivatives, in which Job becomes more positive with increasing electronegativity, and in ring-substituted toluenes, having both a nitro and an oxygen group which exert significant bond-fixing effects.

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Reference：
Benzofuran – Wikipedia,
Benzofuran | C8H2443O – PubChem

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In order to discover a novel type of analgesic, we investigated dual activity ligands with TRPV1 antagonism and mu-opioid receptor affinity with the goal of eliciting synergistic analgesia while avoiding the side effects associated with single targeting. Based on a combination approach, a series of 4-benzyl-4-(dimethylamino)piperidinyl analogues were designed, synthesized and evaluated for their receptor activities. Among them, compound 49 exhibited the most promising dual-acting activity toward TRPV1 and the mu-opioid receptor in vitro. In vivo, 49 displayed potent, dose-dependent antinociceptive activity in both the 1st and 2nd phases in the formalin assay. Consistent with its postulated mechanism, we confirmed that in vivo, as in vitro, compound 49 both antagonized TRPV1 and functioned as a mu-opioid agonist. This result indicates that dual-acting TRPV1 antagonist/mu-opioid ligands can be made and represent a new and promising class of analgesic.

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Benzofuran – Wikipedia,
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Novel substituted 2,3-dihydrobenzofuran-7-carboxamide (DHBF-7-carboxamide) and 2,3-dihydrobenzofuran-3(2H)-one-7-carboxamide (DHBF-3-one-7-carboxamide) derivatives were synthesized and evaluated as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). A structure-based design strategy resulted in lead compound 3 (DHBF-7-carboxamide; IC50 = 9.45 muM). To facilitate synthetically feasible derivatives, an alternative core was designed, DHBF-3-one-7-carboxamide (36, IC50 = 16.2 muM). The electrophilic 2-position of this scaffold was accessible for extended modifications. Substituted benzylidene derivatives at the 2-position were found to be the most potent, with 3?,4?-dihydroxybenzylidene 58 (IC50 = 0.531 muM) showing a 30-fold improvement in potency. Various heterocycles attached at the 4?-hydroxyl/4?-amino of the benzylidene moiety resulted in significant improvement in inhibition of PARP-1 activity (e.g., compounds 66-68, 70, 72, and 73; IC50 values from 0.718 to 0.079 muM). Compound 66 showed selective cytotoxicity in BRCA2-deficient DT40 cells. Crystal structures of three inhibitors (compounds (-)-13c, 59, and 65) bound to a multidomain PARP-1 structure were obtained, providing insights into further development of these inhibitors.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H2448O – PubChem

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We synthesized a series of novel 3-phenyl-4-benzylaminopiperidine derivatives that were identified as potent tachykinin NK1 receptor antagonists by structural modification of the 3-benzhydrylpiperidone derivative through high-throughput screening. N-{2-[(3R,4S)-4-({2-Methoxy-5-[5-(trifluoromethyl)- 1Htetrazol-1-yl]benzyl}amino)-3-phenyl-1-piperidinyl]-2-oxoethyl}acetamide ((+)-39) was found to be one of the most potent tachykinin NK1 receptor antagonists with high metabolic stability. Highly efficient asymmetric synthesis of (+)-39 was achieved via dynamic kinetic resolution.

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Reference：
Benzofuran – Wikipedia,
Benzofuran | C8H2450O – PubChem

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Tricyclic furo-quinazolinones

Anti-inflammatories and analgesics of the formula SPC1 Wherein X y is –OCH2 CH2 — or –CH2 CH2 O–, R is lower alkyl, allyl or cycloalkylalkyl and R’ is phenyl or phenyl monosubstituted by halo, alkyl, alkoxy or trifluoromethyl, Are prepared by oxidation of the corresponding dihydro intermediates.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H2441O – PubChem

Discovery of 5-Nitro-2,3-dihydrobenzofuran

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Nonsteroidal dissociated glucocorticoid agonists containing azaindoles as steroid A-ring mimetics

Syntheses and structure-activity relationships (SAR) of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain azaindole moieties as A-ring mimetics and display various degrees of in vitro dissociation between gene transrepression and transactivation. Collagen induced arthritis studies in mouse have demonstrated that in vitro dissociated compounds (R)-16 and (R)-37 have steroid-like anti-inflammatory properties with improved metabolic side effect profiles, such as a reduced increase in body fat and serum insulin levels, compared to steroids.

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Benzofuran – Wikipedia,
Benzofuran | C8H2449O – PubChem

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Chromium-Catalyzed Activation of Acyl C-O Bonds with Magnesium for Amidation of Esters with Nitroarenes

Here, we report a chromium-catalyzed activation of acyl C-O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.

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Benzofuran – Wikipedia,
Benzofuran | C8H2447O – PubChem

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GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF

Compounds of Formula (IA) and Formula (IB) wherein R1, R2, R3, R4, R5, and R6 are as defined herein for Formula (IA) or Formula (IB), or a tautomer, prodrug, solvate,or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

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Benzofuran – Wikipedia,
Benzofuran | C8H2440O – PubChem

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In vitro intrinsic clearance-based optimization of N3- phenylpyrazinones as corticotropin-releasing factor-1 (CRF1) receptor antagonists

A series of pyrazinone-based heterocycles was identified as potent and orally active corticotropinreleasing factor-1 (CRF1) receptor antagonists. Selected compounds proved efficacious in an anxiety model in rats; however, pharmacokinetic properties were not optimal. In this article, we describe an in vitro intrinsic clearance-based approach to the optimization of pyrazinone-based CRF1 receptor antagonists wherein sites of metabolism were identified by incubation with human liver microsomes. It was found that the rate of metabolism could be decreased by incorporation of appropriate substituents at the primary sites of metabolism. This led to the discovery of compound 12x, a highly potent (IC50 = 1.0 nM) and selective CRF1 receptor antagonist with good oral bioavailability (F = 52%) in rats and efficacy in the defensive withdrawal anxiety test in rats.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H2444O – PubChem