- 3-Nitrodibenzofuran and 3-Iododibenzofuran
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The structures of 3-nitrodibenzofuran, C12H7NO3, and 3-iododibenzofuran, C12H7IO, have been determined.Both molecules are nearly planar and pack in herringbone patterns composed of symmetry related head-to-tail pairs with parallel ? systems.
- Chaloner, Penny A.,Hitchcock, Peter B.,Sutton, Peter G.
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Read Online
- Triarylated amine derivative and organic electroluminescence device with same
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The invention discloses a triarylated amine derivative and an organic electroluminescence device with the same, and relates to the technical field of organic photoelectric materials. The triarylated amine derivative has a large conjugated system, thereby having high hole mobility and presenting good hole transmissibility; in addition, the triarylated amine derivative has high thermal stability anddissolubility and is beneficial for material film forming. The organic electroluminescence device comprises a cathode, an anode and one or more organic matter layers. The organic matter layers are located between the cathode and the anode. At least one of the organic matter layers contains the triarylated amine derivative. The organic electroluminescence device has low driving voltages, high light-emitting efficiency, light-emitting luminance and long service life.
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Paragraph 0139; 0139; 0140; 0141
(2018/09/08)
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- NOVEL TRIAZINE COMPOUND, AND ORGANIC ELECTRONIC ELEMENT AND PLANT-GROWING LIGHTING THAT USE THE SAME
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PROBLEM TO BE SOLVED: To provide a triazine compound which has a high triplet energy level and excellent heat resistance, and can be used as an organic electronic element material realizing an element with high efficiency, low voltage and a long life. SOLUTION: In the triazine compound, as represented by the general formula [1] in the figure, a triazine backbone moiety is linked to a dibenzofuran or dibenzothiophene backbone moiety via a biphenyl backbone moiety, where X is an oxygen atom or sulfur atom. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
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Paragraph 0077
(2018/07/28)
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- Visible-Light-Promoted Synthesis of Dibenzofuran Derivatives
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Dibenzofurans are naturally occurring molecules that have received considerable attention for a variety of practical applications, such as in pharmaceuticals and electronic materials. Herein, an efficient and eco-friendly method for the synthesis of dibenzofuran derivatives via intramolecular C-O bond formation, which involves the in situ production of a diazonium salt, is described. The transformation requires a diazotizing agent and is promoted by the use of an organic photosensitizer under visible-light irradiation.
- Cho, Ji Young,Roh, Geum-Bee,Cho, Eun Jin
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p. 805 - 811
(2018/01/28)
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- With Wnt signal path to inhibit the active heterocyclic compounds (by machine translation)
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The invention relates to a signal path with Wnt inhibiting activity of a heterocyclic compound, including the compound and its pharmaceutically acceptable salt, various isotope, various isomers or various crystal structure, having the general formula I of the structure shown in: the invention relates to a compound and its joint application composition can effectively inhibit the Wnt signal path, can be used for the treatment or prevention of a disorder associated with a Wnt signal path. (by machine translation)
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Paragraph 0061-0065
(2017/08/15)
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- A thermally stable anthracene derivative for application in organic thin film transistors
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A novel multifunctional anthracene derivative 2,6-bis(dibenzo[b,d]furan-3-yl)anthracene) (BDBFAnt), by coupling anthracene moiety with dibenzo[b,d]furan units attached to its peripheral position, has been designed and synthesized for application in OTFT devices. Introduction of dibenzo[b,d]furan units in OTFTs is the first example and is highly innovative due to their suitable carrier transport ability, excellent thermal stability, fine film-forming property, rigid planarity and outstanding fluorescence. The fabricated OTFTs demonstrate a decent hole mobility (3.0?cm2/V s) and favorable green solid fluorescence with excellent thermal stability (up to 220?°C), which expound on the great potential of our material in organic electronics.
- Zhao, Yang,Yan, Lijia,Murtaza, Imran,Liang, Xiao,Meng, Hong,Huang, Wei
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p. 105 - 111
(2017/01/25)
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- Microwave-Promoted Pd-Catalyzed Synthesis of Dibenzofurans from Ortho-Arylphenols
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ortho-Aryl phenols, synthesized via protecting group free Suzuki–Miyaura coupling of ortho-halophenols and arene boronic acids, undergo a cyclization to dibenzofurans via oxidative C–H activation. The reaction proceeds under microwave irradiation in short reaction times using catalytic amounts of Pd(OAc)2 without additional ligands.
- Schmidt, Bernd,Riemer, Martin
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p. 1287 - 1297
(2017/03/27)
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- Phosphorescent iridium complex containing 3-phenyl pyridazine structure, and applications thereof
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The invention discloses a phosphorescent iridium complex containing a 3-phenyl pyridazine structure, and applications thereof. Metal iridium is taken as the inner core of the phosphorescent iridium complex, and the phosphorescent iridium complex is taken
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Paragraph 0055; 0056; 0057
(2016/10/10)
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- Phosphorescent iridium complex serving as OLED (organic light emitting diode) doping material
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The invention discloses a phosphorescent iridium complex serving as an OLED (organic light emitting diode) doping material. According to the iridium complex, metal iridium is taken as a structural inner core and applied to an OLED device and can emit phos
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Paragraph 0054; 0055; 0056
(2016/10/10)
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- N-(2-ARYLETHYL) BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR
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The present invention relates to the use compounds of formula I which are antagonists of the 5-HT 6 receptor, for treating a cognitive disorder selected from the group consisting of age-related cognitive decline, mild cognitive impairment and dementia
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Paragraph 0139
(2016/01/25)
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- Double functionalization of 2-amino-2′-hydroxy-1,1′-biaryls: Synthesis of 4-nitro-dibenzofurans and benzofuro-indoles
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Several substituted 2′-amino-biphenyl-2-ols were synthesized. The mild and TM-free double functionalization: nitration and cycloetherification of 2′-amino-biphenyl-2-ols have been achieved for the synthesis of functionalized 4-nitro-dibenzofurans utilizing NaNO2 in TFA and water. Interestingly, nitration of phenol ring was observed along with the dibenzofuran ring formation in the one-pot synthesis. The position of the nitro group in several dibenzofurans is also established by X-ray crystal structure studies. Further functionalization of the obtained 4-nitro-dibenzofurans has been carried into 3-nitro-terphenyl-2-ol, novel benzofuro-indoles, and amino-dibenzofurans. The mechanistic understanding on double functionalization of 2′-amino-biphenyl-2-ols suggests that reaction proceeds by a combination of nitration of the phenol ring followed by Sandmeyer reaction for dibenzofuran ring formation.
- Kumar, Amit,Sattar, Moh.,Verma, Ajay,Dara, Ankit,Kumar, Sangit
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p. 44728 - 44741
(2015/06/02)
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- BRIDGED BENZIMIDAZOLE-CARBENE COMPLEXES AND USE THEREOF IN OLEDS
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The present invention concerns a metal-carbene complex of the general formula (I) in which R5 and R6 together, or R6 and R7 together, a unit of the formula: in which * denotes the connection to the carbon atoms
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Page/Page column 54
(2012/03/09)
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- Discovery of potent and selective matrix metalloprotease 12 inhibitors for the potential treatment of chronic obstructive pulmonary disease (COPD)
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Chronic obstructive pulmonary disease (COPD) is an inflammatory lung disease associated with irreversible progressive airflow limitation. Matrix metalloproteinase-12 (MMP-12) has been characterized to be one of the major proteolytic enzymes to induce airway remodeling, destruction of elastin and the aberrant remodeling of damaged alveoli in COPD and asthma. The goal of this project is to develop and identify an orally potent and selective small molecule inhibitor of MMP-12 for treatment of COPD and asthma. Syntheses and structure-activity relationship (SAR) studies of a series of dibenzofuran (DBF) sulfonamides as MMP-12 inhibitors are described. Potent inhibitors of MMP-12 with excellent selectivity against other MMPs were identified. Compound 26 (MMP118), which exhibits excellent oral efficacy in the MMP-12 induced ear-swelling inflammation and lung inflammation mouse models, had been successfully advanced into Development Track status.
- Wu, Yuchuan,Li, Jianchang,Wu, Junjun,Morgan, Paul,Xu, Xin,Rancati, Fabio,Vallese, Stefania,Raveglia, Luca,Hotchandani, Rajeev,Fuller, Nathan,Bard, Joel,Cunningham, Kristina,Fish, Susan,Krykbaev, Rustem,Tam, Steve,Goldman, Samuel J.,Williams, Cara,Mansour, Tarek S.,Saiah, Eddine,Sypek, Joseph,Li, Wei
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scheme or table
p. 138 - 143
(2012/02/16)
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- 7-Amino-dibenzofuran-3-carboxylate: A new probe for femtosecond dynamic microsolvation studies of biomolecules
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The reorientational dynamics of a polar environment, for example water in the hydration shell of biomolecules, can be measured with a molecular probe by time-resolving its fluorescence Stokes shift. The new probe 7-amino- dibenzofuran-3-carboxylate (ADC)
- Berndt, Falko,Ioffe, Ilya,Granovsky, Alexander A.,Mahrwald, Rainer,Tannert, Sebastian,Kovalenko, Sergey A.,Ernsting, Nikolaus P.
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scheme or table
p. 164 - 170
(2012/06/18)
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- PHOSPHORESCENT EMITTERS
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Compounds including a ligand with a dibenzo-fused 5-membered ring substituent are provided. In particular, the compounds may be iridium complexes including imidazole coordinated to the dibenzo-substituted ligand. The dibenzo-fused 5-membered ring moiety of the ligand may be twisted or minimally twisted out of plane with respect to the rest of the ligand structure. The compound may be used in organic light emitting devices, particularly as emitting dopants in blue devices. Devices comprising the compounds may demonstrate improved stability while maintaining excellent color.
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- TRICYCLIC COMPOUNDS AS MATRIX METALLOPROTEINASE INHIBITORS
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The present teachings relate to compounds of formula I: and pharmaceutically acceptable salts and esters thereof, wherein R1, R2, R3, R4, X, and Y are as defined herein. The present teachings also provide methods of making the compounds of formula I and methods of inhibiting matrix metalloproteinases, in particular, MMP-12, that may be involved in pathological disorders found in mammals, including a human.
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Page/Page column 27
(2010/09/17)
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- HETEROLEPTIC IRIDIUM COMPLEX
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Novel compounds comprising heteroleptic iridium complexes are provided. The compounds have a particular combination of ligands which includes a single pyridyl dibenzo-substituted ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants, to provide devices having improved efficiency, lifetime, and manufacturing.
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- A selective matrix metalloprotease 12 inhibitor for potential treatment of chronic obstructive pulmonary disease (COPD): Discovery of (S)- 2-(8-(Methoxycarbonylamino)dibenzo[b,d]furan- 3-sulfonamido)-3-methylbutanoic acid (MMP408)
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Matrix metalloprotease 12 plays a significant role in airway inflammation and remodeling. Increased expression and production of MMP-12 have been found in the lung of human COPD patients. MMP408 (14), a potent and selective MMP-12 inhibitor, was derived from a potent matrix metalloprotease 2 and 13 inhibitor via lead optimization and has good physical properties and bioavailability. The compound blocks rhMMP-12-induced lung inflammation in a mouse model and was advanced for further development for the treatment of COPD.
- Wei, Li,Jianchang, Li,Yuchuan, Wu,Junjun, Wu,Hotchandani, Rajeev,Cunningham, Kristina,McFadyen, Iain,Bard, Joel,Morgan, Paul,Schlerman, Franklin,Xin, Xu,Tam, Steve,Goldman, Samuel J.,Williams, Cara,Sypek, Joseph,Mansour, Tarek S.
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supporting information; experimental part
p. 1799 - 1802
(2009/12/07)
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- TRICYCLIC COMPOUNDS AS MATRIX METALLOPROTEINASE INHIBITORS
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The present invention relates to compositions of the formula (I): and pharmaceutically acceptable salts, hydrates, or esters thereof, wherein R1, R2, R3, R4, R5, X, and Y are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating pathologic conditions or disorders mediated wholly or in part by matrix metalloproteinases, such as asthma and chronic obstructive pulmonary disease, comprising administering a therapeutically effective amount of a compound of formula (I) to a mammal (e.g., a human) in need thereof.
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Page/Page column 60-61
(2008/12/05)
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- Synthesis and biological activity of various derivatives of a novel class of potent, selective, and orally active prostaglandin D2 receptor antagonists. 1. Bicyclo[2.2.1]heptane derivatives
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Novel prostaglandin D2 (PGD2) receptor antagonists were synthesized as a potential new class of antiallergic agents having a bicyclo[2.2.1] heptane ring system with sulfonamide groups. Some of them exhibit extremely potent antagonism of the PGD2 receptor in radioligand binding and cAMP formation assays with IC50 values below 50 nM and much less antagonism of TXA2 and PGI2 receptors. These potent PGD2 receptor antagonists, when given orally, dramatically suppress various allergic inflammatory responses such as increased vascular permeability in allergic rhinitis, conjunctivitis, and asthma models. The excellent pharmacological profiles of PGD2 receptor antagonists, originally synthesized in our laboratories, are of potentially great clinical significance. This study also provides experimental evidence suggesting that PGD2 plays an important role in the pathogenesis of allergic diseases.
- Mitsumori, Susumu,Honma, Tsunetoshi,Tsuri, Tatsuo,Hiramatsu, Yoshiharu,Okada, Toshihiko,Hashizume, Hiroshi,Inagaki, Masanao,Arimura, Akinori,Yasui, Kiyoshi,Asanuma, Fujio,Kishino, Junji,Ohtani, Mitsuaki
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p. 2436 - 2445
(2007/10/03)
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- Lithiation of pivaloylamino derivatives of dibenzofuran and 9-methylcarbazole
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2-, 3- and 4-Pivaloylamino derivatives of dibenzofuran [compounds (5), (4) and (6), respectively] and analogous 3-, 2- and 1-substituted derivatives of 9-methylcarbazole [compounds (8), (7) and (9), respectively] were subjected to lithiation at 0°C and subsequent reaction with dimethylformamide. Aldehyde formation took place at positions α to δ to the heteroatom as follows: α for (4) and (7); δ for (5); δ and β (3 : 1) for (8); and α′ (6). No formylation occurred with (9).
- Deady,Sette
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p. 177 - 180
(2007/10/03)
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- Electroreduction of 2- and 3-Chlorodibenzofuran in Deuterated Methanol
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The cathodic reduction of dibenzofuran (2), 2-chlorodibenzofuran (4), and 3-chlorodibenzofuran (1) in deuterated methanol is investigated. The Birch-type reduction product 1,4-dibenzofuran (3) is formed from 1 via 2, whereas 2-chloro-1,4-dihydrodibenzofuran (5) is obtained as by-product besides 3 from 4 as starting compound. Deuterium is only incorporated into the reduction products if CH3OD or CD3OD but not if CD3OH are used. This observation is strongly indicative of a polar mechanism involving protonation rather than a radical mechanism with hydrogen atom abstraction to be operative.
- Voss, Juergen,Waller, Edgar,Kraenke, Petra
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p. 430 - 436
(2007/10/03)
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- Photochemical nitration by tetranitromethane part XXX. Product isolation and identification in the photochemical reaction of dibenzofuran
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The photolysis of the charge-transfer complex of dibenzofuran (1) and tetranitromethane in either dichloromethane or acetonitrile gives t-2-nitro-r-1-trinitromethyl-1,2-dihydrodibenzofuran (4), the epimeric 4-nitro-1-trinitromethyl-1,4-dihydrodibenzofurans 5 and 7, the epimeric 4-hydroxy-1-trinitromethyl-1,4-dihydrodibenzofurans 6 and 8, 3-trinitromethyldibenzofuran (13), and the four isomeric nitrodibenzofurans 9-12. The five adducts 4-8 are formed via attack by trinitromethanide ion at C1 of the dibenzofuran radical cation, while 3-trinitromethyldibenzofuran is formed by decomposition of an adduct, itself formed via initial attack of trinitromethanide ion at C3 of the dibenzofuran radical cation. The regiochemistry of attack of trinitromethanide ion on the radical cation of the non-alternant dibenzofuran system is in keeping with earlier theoretical predictions. In 1,1,1,3,3,3-hexafluoropropan-2-ol solution the analogous photolysis of the charge-transfer complex of dibenzofuran (1) and tetranitromethane gives only the four nitrodibenzofurans 9-12, the attack of trinitromethanide ion on the radical cation of dibenzofuran being suppressed by the solvent. X-Ray crystal structures are reported for compounds 4, 6 and 13, compound 6 representing the first hydroxytrinitromethyl adduct to be unambiguously assigned this structure. Acta Chemica Scandinavica 1996.
- Butts, Craig P.,Eberson, Lennart,Hartshorn, Michael P.,Robinson, Ward T.,Wood, Bryan R.
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p. 587 - 595
(2007/10/03)
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- Photochemical Nitration by Tetranitromethane. III. On the Anomalous Nitration and Oxidative Substitution of Dibenzofuran and a Novel Test of the Shaik-Pross Model of Radical Cation Reactivity
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The photochemical reaction of dibenzofuran and tetranitromethane in dichloromethane gives predominantly nitro/trinitromethyl adducts and only a small amount of nitro-substitution products.The adducts originate from the reaction between photochemically produced trinitromethanide ion and (dibenzofuran)cation radical, followed by reaction of the trinitromethyl-substituted cyxlohexadienyl radical with NO2.The main sites of attack of trinitromethanide ion are the 1- and the 3-positions.The adducts rapidly eliminate nitroform in the presence of a hindered base.Thus photolysis with with such a base present gives directly a mixture containing predominantly 2- and 4-nitrodibenzofuran.The unexpected attack of trinitromethanide at the 3-position of (dibenzofuran)cation radical is also found in more typical oxidative substitution reactions, such as acetoxylation and cyanation.This isomer distribution is distinctly different from that of electropholic substitution in dibenzofuran (attack at the 2-position), a non-alternant conjugated system.The Shaik-Pross treatment of the radical cation/nucleophile elementary step predicts that the spin density of the corresponding triplet should govern the isomer distribution, and CASSCF calculations show that (dibenzofuran)cation radical then should react predominantly in the 3-position.Thus the electrophilic reactivity of the radical cations of non-alternant systems constitutes a novel test of the configuration mixing model.It is also concluded that the unusual substitution pattern of dibenzofuran with respect to electrophilic nitration is due to incursion of the nitrous acid catalyzed (NAC) reaction.
- Eberson, Lennart,Hartshorn, Michael P.,Radner, Finn,Merchan, Manuela,Roos, Bjoern O.
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p. 176 - 183
(2007/10/02)
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- Positional Reactivity of Dibenzofuran in Electrophilic Substitutions
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Isomer distributions of dibenzofuran (DBF) in Friedel-Crafts acylations, Friedel-Crafts alkylations, and nitrations have been determined.The 2- and 3-positions of DBF represents most of the total reactivity.However, the ratio of 2- to 3-isomers greatly varied, depending on the nature of the electrophile.The positional reactivities have been found to be in the following sequence: 2- > 3- > 1- > 4-positions for Friedel-Crafts acylations, Friedel-Crafts benzylations, and nitrations with alkyl nitrate/Lewis acid or nitronium tetrafluoroborate.The ratios for acylations varied over a range from 13.1 to 2.9, while for benzylations and nitrations from 2.0 to 1.0.In contrast, for nitrations of DBF with nitric acid a different reactivity order was found: 3- > 2- > 1- > 4-, with the ratio varying from 0.8 to 0.03 depending on the nature of solvents used.The selectivity for the 3-substitution increased with increase in nitronium ion-like character of nitrating reagents.In particular, nitration with nitric acid in dichloromethane gave mostly 3-nitro-DBF (95percent of the four possible isomeric mixture).The charge-transfer nitration with tetranitromethane under the UV irradiation has shown a similar isomer distribution to that in nitration with nitric acid.The MNDO calculations predicts that the late transition-state model (by ?-complex) favors reactions at the 2-position while the early transition-state model (by HOMO electron density) leads to the 3-substitution.
- Keumi, Takashi,Tomioka, Naoto,Hamanaka, Kozo,Kakihara, Hirohito,Fukishima, Masahiko,et al.
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p. 4671 - 4677
(2007/10/02)
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- A Short Synthesis of Dibenzofurans and Dibenzothiophenes
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An afficient synthesis of dibenzofurans and dibenzothiophenes from aryl salicylates is described, which involves a novel rearrangement-extrusion-cyclisation sequence of o-substituted phenoxyl and thiophenoxyl radicals.
- Black, Michael,Cadogan, J. I. G.,McNab, Hamish
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p. 395 - 396
(2007/10/02)
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- A Remarkable Difference of the Positional Selectivity in Electrophilic Aromatic Substitution of Dibenzofuran between the Classical ?-Complex and Charge-Transfer Mechanisms
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Electrophilic nitration of dibenzofuran with nitric acid by a charge-transfer mechanism occurs exclusively at the 3-position and on the other hand, substitution at the 2-position predominates in the acylation, in which a classical ?-complex mechanism is important.
- Keumi, Takashi,Hamanaka, Kozo,Hasegawa, Haruo,Minamide, Naoki,Inoue, Yoshinori,Kitajima, Hidehiko
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p. 1285 - 1288
(2007/10/02)
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- Regioselective Preparation of 2- and 3-Nitrodibenzofurans by the Direct Nitration of Dibenzofuran
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Nitration of dibenzofuran with nitric acid in trifluoroacetic acid gave 3-nitrodibenzofuran selectively under very mild conditions.In contrary, the Friedel-Crafts type nitration using alkyl nitrates and aluminium chloride in nitromethane gave 2-nitrodibenzofuran as the main product.
- Keumi, Takashi,Yamada, Hideyo,Takahashi, Hisakazu,Kitajima, Hidehiko
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p. 629 - 630
(2007/10/02)
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