InBr3-promoted divergent approach to polysubstituted indoles and quinolines from 2-ethynylanilines: switch from an intramolecular cyclization to an intermolecular dimerization by a type of terminal substituent group.

PubWeight™: 1.06‹?› | Rank: Top 10%

🔗 View Article (PMID 18442294)

Published in J Org Chem on April 29, 2008

Authors

Norio Sakai1, Kimiyoshi Annaka, Akiko Fujita, Asuka Sato, Takeo Konakahara

Author Affiliations

1: Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, Noda, Chiba, Japan. sakachem@rs.noda.tus.ac.jp

Articles by these authors

Biological activity of the Helicobacter pylori virulence factor CagA is determined by variation in the tyrosine phosphorylation sites. Proc Natl Acad Sci U S A (2002) 3.50

Actin polymerization-driven molecular movement of mDia1 in living cells. Science (2004) 2.80

Actin turnover-dependent fast dissociation of capping protein in the dendritic nucleation actin network: evidence of frequent filament severing. J Cell Biol (2006) 1.70

The roles of fission yeast ase1 in mitotic cell division, meiotic nuclear oscillation, and cytokinesis checkpoint signaling. Mol Biol Cell (2005) 1.66

The gamma-tubulin complex protein Alp4 provides a link between the metaphase checkpoint and cytokinesis in fission yeast. Genes Cells (2002) 1.02

Augmented autocrine bone morphogenic protein (BMP) 7 signaling increases the metastatic potential of mouse breast cancer cells. Clin Exp Metastasis (2012) 1.02

Chemokine CCL2/MCP-1 negatively regulates metastasis in a highly bone marrow-metastatic mouse breast cancer model. Clin Exp Metastasis (2009) 0.99

RECK forms cowbell-shaped dimers and inhibits matrix metalloproteinase-catalyzed cleavage of fibronectin. J Biol Chem (2008) 0.96

Inhibitors of fibril formation and cytotoxicity of beta-amyloid peptide composed of KLVFF recognition element and flexible hydrophilic disrupting element. Biochem Biophys Res Commun (2002) 0.92

A novel transgenic mouse model of the human multiple myeloma chromosomal translocation t(14;16)(q32;q23). Cancer Res (2011) 0.92

Functional dissection of the gamma-tubulin complex by suppressor analysis of gtb1 and alp4 mutations in Schizosaccharomyces pombe. Genetics (2004) 0.88

Interaction-based evaluation of the propensity for amyloid formation with cross-beta structure. Biochem Biophys Res Commun (2006) 0.88

Overexpression of RORγt under control of the CD2 promoter induces polyclonal plasmacytosis and autoantibody production in transgenic mice. Eur J Immunol (2012) 0.85

3-benzylamino-β-carboline derivatives induce apoptosis through G2/M arrest in human carcinoma cells HeLa S-3. Eur J Med Chem (2010) 0.83

Higher-order molecular packing in amyloid-like fibrils constructed with linear arrangements of hydrophobic and hydrogen-bonding side-chains. J Mol Biol (2005) 0.82

An efficient one-pot synthesis of unsymmetrical ethers: a directly reductive deoxygenation of esters using an InBr3/Et3SiH catalytic system. J Org Chem (2007) 0.82

MafA-deficient and beta cell-specific MafK-overexpressing hybrid transgenic mice develop human-like severe diabetic nephropathy. Biochem Biophys Res Commun (2009) 0.81

[A comparison of susceptibility of Pseudomonas aeruginosa clinical isolates to carbapenem antibiotics in our hospital]. Jpn J Antibiot (2014) 0.81

Postictal suppression correlates with therapeutic efficacy for depression in bilateral sine and pulse wave electroconvulsive therapy. Psychiatry Clin Neurosci (2007) 0.80

An unprecedented approach to 4,5-disubstituted pyrimidine derivatives by a ZnCl(2)-catalyzed three-component coupling reaction. Org Lett (2009) 0.79

The rainbow trout CMP-sialic acid synthetase utilises a nuclear localization signal different from that identified in the mouse enzyme. Glycobiology (2007) 0.78

Orientation of dye molecules in DNA-based films with chain alignment and judgment of their DNA-binding modes. J Phys Chem B (2005) 0.78

Palladium-catalyzed coupling reaction of terminal alkynes with aryl iodides in the presence of indium tribromide and its application to a one-pot synthesis of 2-phenylindole. Org Lett (2004) 0.78

Postictal cardiovascular response predicts therapeutic efficacy of electroconvulsive therapy for depression. Psychiatry Clin Neurosci (2007) 0.78

A single-step synthesis of enynes: Pd-catalyzed arylalkynylation of aryl iodides, internal alkynes, and alkynylsilanes. Org Lett (2010) 0.77

Cloning and heterologous expression of the antibiotic peptide (ABP) genes from Rhizopus oligosporus NBRC 8631. Biosci Biotechnol Biochem (2005) 0.77

Analysis of fibril formation of amyloid-beta-protein by stretched exponential function. Protein Pept Lett (2003) 0.77

Different effects of smoke from heavy and light cigarettes on the induction of bronchial smooth muscle hyperresponsiveness in rats. J Smooth Muscle Res (2011) 0.77

Sialome analysis of the cephalochordate Branchiostoma belcheri, a key organism for vertebrate evolution. Glycobiology (2011) 0.77

Highly selective conversion of nitrobenzenes using a simple reducing system combined with a trivalent indium salt and a hydrosilane. Chem Commun (Camb) (2010) 0.76

Direct synthesis of polysubstituted quinoline derivatives by InBr3-promoted dimerization of 2-ethynylaniline derivatives. J Org Chem (2006) 0.76

Spontaneous germline excision of Tol1, a DNA-based transposable element naturally occurring in the medaka fish genome. Genome (2014) 0.75

Augmented bronchial smooth muscle contractility induced by aqueous cigarette smoke extract in rats. J Smooth Muscle Res (2014) 0.75

3-(3-Phenoxybenzyl)amino-β-carboline: a novel antitumor drug targeting α-tubulin. Bioorg Med Chem Lett (2011) 0.75

New approach to the practical synthesis of tri- or tetrasubstituted pyrimidine derivatives: a four-component coupling reaction from a functionalized silane, two types of aromatic nitriles, and acetals. Org Lett (2005) 0.75

Clinical Characteristics of Methicillin-resistant Coagulase-negative Staphylococcal Bacteremia in a Tertiary Hospital. Intern Med (2017) 0.75

Novel synthesis of 7-fluoro-8-(trifluoromethyl)- 1H-1,6-naphthyridin-4-one derivatives: intermolecular cyclization of an N-silyl-1-azaallyl anion with perfluoroalkene and subsequent intramolecular skeletal transformation of the resulting pentasubstituted pyridines. J Org Chem (2007) 0.75

Involvement of methionine salvage pathway genes of Saccharomyces cerevisiae in the production of precursor compounds of dimethyl trisulfide (DMTS). J Biosci Bioeng (2013) 0.75

The aminomethylation of electron-rich aromatics with an N-silyl-N,O-acetal catalyzed by a metal triflate-TMSCl system: facile synthesis of aromatic primary amines, 1-aryl-trichloroethylamines. J Org Chem (2003) 0.75

Structure-activity relationship in the antitumor activity of 6-, 8- or 6,8-substituted 3-benzylamino-β-carboline derivatives. Bioorg Med Chem Lett (2012) 0.75

Me3SiCl-promoted three-component coupling reaction of a functionalized enamine, an acetal, and an alkyne: an unprecedented approach to the synthesis of tetrasubstituted pyridines via a [3 + 2 + 1] intermolecular cyclization. J Org Chem (2008) 0.75

Association between CT-Diagnosed Pneumonia and Endoscopic Submucosal Dissection of Gastric Neoplasms. Digestion (2016) 0.75

Copper-catalyzed three- five- or seven-component coupling reactions: the selective synthesis of cyanomethylamines, N,N-bis(cyanomethyl)amines and N,N'-bis(cyanomethyl)methylenediamines based on a Strecker-type synthesis. Molecules (2013) 0.75

Peripheral region for core cross-beta plays important role in amyloidogenicity. Biochem Biophys Res Commun (2006) 0.75

Annexin A3 as a negative regulator of adipocyte differentiation. J Biochem (2012) 0.75

Copper-catalyzed [5+1] annulation of 2-ethynylanilines with an N,O-acetal leading to construction of quinoline derivatives. Org Lett (2012) 0.75

Anti-oxidative activity of hydrolysate from rice bran protein in HepG2 cells. Biol Pharm Bull (2017) 0.75

Gallium-catalyzed reductive chlorination of carboxylic acids with copper(II) chloride. J Org Chem (2014) 0.75

Hf(OTf)4-catalyzed regioselective n-aminomethylation of indoles and related NH-containing heterocycles. J Org Chem (2010) 0.75

Molecular orientation of porphyrins accompanying the formation of chain-aligned DNA films. Biomacromolecules (2005) 0.75

Augmented bronchial smooth muscle contractility induced by aqueous cigarette smoke extract in rats. J Smooth Muscle Res (2014) 0.75

Indium(III)-catalyzed reductive bromination and iodination of carboxylic acids to alkyl bromides and iodides: scope, mechanism, and one-pot transformation to alkyl halides and amine derivatives. J Org Chem (2013) 0.75

Ictal electroencephalographic correlates of posttreatment neuropsychological changes in electroconvulsive therapy: a hypothesis-generation study. J ECT (2007) 0.75

[A comparison of susceptibility of Pseudomonas aeruginosa clinical isolates to carbapenem antibiotics in our hospital]. Jpn J Antibiot (2014) 0.75

[A case of urgent aortic valve replacement for infective endocarditis in pregnancy]. Masui (2003) 0.75

Single-step thioetherification by indium-catalyzed reductive coupling of carboxylic acids with thiols. Org Lett (2012) 0.75

Synthesis of tri- or tetrasubstituted pyrimidine derivatives through the [5+1] annulation of enamidines with either N,N-dimethylformamide dialkyl acetals or orthoesters and their application in a ring transformation of pyrimidines to pyrido[2,3-d]pyrimidin-5-one derivatives. Chemistry (2011) 0.75

Indium-catalyzed reductive bromination of carboxylic acids leading to alkyl bromides. Org Lett (2012) 0.75

Lifestyle and psychological distress in medical school students. Med Teach (2011) 0.75

Judgment for DNA-binding modes of dye molecules by novel chain-aligned film method. Nucleic Acids Symp Ser (Oxf) (2005) 0.75