- Bridging Small Molecules to Conjugated Polymers: Efficient Thermally Activated Delayed Fluorescence with a Methyl-Substituted Phenylene Linker
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Based on a “TADF + Linker” strategy (TADF=thermally activated delayed fluorescence), demonstrated here is the successful construction of conjugated polymers that allow highly efficient delayed fluorescence. Small molecular TADF blocks are linked together
- Rao, Jiancheng,Liu, Xinrui,Li, Xuefei,Yang, Liuqing,Zhao, Lei,Wang, Shumeng,Ding, Junqiao,Wang, Lixiang
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Read Online
- Anthraquinone-based intramolecular charge-transfer compounds: Computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence
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Red fluorescent molecules suffer from large, non-radiative internal conversion rates (kIC) governed by the energy gap law. To design efficient red thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs), a large fluorescence rate (kF) as well as a small energy difference between the lowest singlet and triplet excited states (ΔEST) is necessary. Herein, we demonstrated that increasing the distance between donor (D) and acceptor (A) in intramolecular-charge-transfer molecules is a promising strategy for simultaneously achieving small ΔEST and large kF. Four D-Ph-A-Ph-D-type molecules with an anthraquinone acceptor, phenyl (Ph) bridge, and various donors were designed, synthesized, and compared with corresponding D-A-D-type molecules. Yellow to red TADF was observed from all of them. The kF and ΔEST values determined from the measurements of quantum yield and lifetime of the fluorescence and TADF components are in good agreement with those predicted by corrected time-dependent density functional theory and are approximatively proportional to the square of the cosine of the theoretical twisting angles between each subunit. However, the introduction of a Ph-bridge was found to enhance kF without increasing ΔEST. Molecular simulation revealed a twisting and stretching motion of the N-C bond in the D-A-type molecules, which is thought to lower ΔEST and kF but raise kIC, that was experimentally confirmed in both solution and doped film. OLEDs containing D-Ph-A-Ph-D-type molecules with diphenylamine and bis(4-biphenyl)amine donors demonstrated maximum external quantum efficiencies of 12.5% and 9.0% with emission peaks at 624 and 637 nm, respectively.
- Zhang, Qisheng,Kuwabara, Hirokazu,Potscavage, William J.,Huang, Shuping,Hatae, Yasuhiro,Shibata, Takumi,Adachi, Chihaya
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Read Online
- Dark blue electroluminescent compound and preparation method and application thereof
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The invention discloses a dark blue electroluminescent compound and a preparation method and application thereof, and the compound is 2-(4-(9, 9-dimethylacridin-10(9H)-yl)-2, 5-diR2-based phenyl)-1-(4-R1-based phenyl)-1H-phenanthroimidazole. The preparation method of the compound is easy to operate and high in yield, the compounds exhibit dark blue fluorescence, half-width is less than 60 nm, thenon-doped OLED device prepared by taking the material as a luminescent material produces dark blue emission, a starting voltage is 3.3 V, the maximum brightness is greater than 20,000 cd.m, the external quantum efficiency is still greater than 3% when the brightness is up to 10,000 cd.m, and the material is a dark blue light material with excellent performance.
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Paragraph 0036-0042; 0047-0053
(2020/05/30)
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- Carbazole derivatives and organoelectro luminescent device using the same
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PURPOSE: A carbazole derivative is provided to drive an organic electroluminescent device at low voltage and to improve brightness when the derivative is used in an organic layer of the organic electroluminescent device, thereby improving economic efficiency. CONSTITUTION: A carbazole derivative is denoted by chemical formula 1. An organic electroluminescent device comprises a first electrode, a second electrode, and one or more organic layers between the first and second electrodes. The organic layers contain the carbazole derivative of chemical formula 1. The organic layers are selected among a hole injection layer, a hole transport layer, a functional layer with hole injecting and transporting functions, a light emitting layer, an electrode transport layer, and an electron injection layer. The light emitting layer contains one or more host compounds and one or more dopant compounds. The host compound is a carbazole derivative of chemical formula 1.
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Paragraph 0366-0372
(2020/11/28)
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- Heterocyclic com pounds and organic light-emitting diode including the same
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The present invention relates to a novel heterocyclic compound and an organic electroluminescent device comprising the same. The heterocyclic compound is represented by the following Chemical Formula 1, and the organic electroluminescent device including the heterocyclic compound has excellent driving voltage, luminous efficiency, and lifespan properties. Chemical Formula 1. (by machine translation)
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Paragraph 0444-0450
(2021/01/29)
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- An electroluminescent compound and an electroluminescent device comprising the same
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The present invention relates to an organic luminescent compound represented by chemical formula 1 and an organic electroluminescent device including the same. The organic luminescent compound according to the present invention has excellent luminous efficiency and lifetime properties of material, and thus, enables the manufacturing of an organic electroluminescent device having excellent luminous efficiency while having power efficiency and long lifetime properties. [Chemical formula 1].
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Paragraph 0273; 0280-0285
(2020/12/16)
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- Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same
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The present invention relates to an organic light emitting compound represented by formula A and an organic light emitting diode including the same. Substituents A1 to A4, R1 to R17, X, Y, a, b, m, n, p, L1, and L2 are identical to as defined in the detailed description.
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Paragraph 0354; 0380-0384
(2020/08/29)
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- Deuterated organic compounds for organic light-emitting diode and organic light-emitting diode including the same
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The present invention relates to an organic electroluminescent compound represented by chemical formula A and an organic light emitting device comprising the same. Substituents Y, Ar2 , L3 , K, p and x are as defined in the description of the invention. [Chemical A] (by machine translation)
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Paragraph 0662; 0693-0697
(2020/12/15)
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- Photoelectric conversion element, imaging device, optical sensor, and method of using photoelectric conversion element
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The present invention provides a photoelectric conversion element having a photoelectric conversion film which exhibits excellent photoelectric conversion efficiency and responsiveness, an imaging device, an optical sensor, and a method of using a photoelectric conversion element. In the photoelectric conversion element of the invention, a photoelectric conversion material contains at least one selected from the group consisting of a compound represented by General formula (1), a compound represented by General formula (2), and a compound represented by General formula (3).
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Page/Page column 96-97
(2020/02/29)
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- Thermally-activated delayed fluorescence material and preparation method and application thereof
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The invention relates to a thermally-activated delayed fluorescence material and a preparation method and application thereof. The energy level difference between the singlet state and the triplet states of the thermally-activated delayed fluorescence material is small, so the thermally-activated delayed fluorescence material can be used as an organic light-emitting layer material of an OLED device and can improve the efficiency of the device. The fluorescence material has a molecular structural formula as described in the specification. In the molecular structural formula, R is selected frommethyl, ethyl, propyl, butyl and amyl groups.
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Paragraph 0017; 0037-0040
(2020/11/12)
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- Heterocyclic compound and organic light emitting device including the same
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Provided are a heterocyclic compound and an organic light-emitting device including the same. The heterocyclic compound may be represented by Formula 1: in the Formula 1, A1, X2, Y1, Y2, m1, m2, R10,R20, R30, b10, b20 and b30 are same as described in the description.
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Paragraph 0521-0525
(2020/07/15)
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- Near-Infrared BODIPY-Acridine Dyads Acting as Heavy-Atom-Free Dual-Functioning Photosensitizers
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Boron dipyrromethene (BODIPY) dyes represent a particular class within the broad array of potential photosensitizers. Their highly fluorescent nature opens the door for theragnostic applications, combining imaging and therapy using a single, easily synthesized chromophore. However, near-infrared absorption is strongly desired for photodynamic therapy to enhance tissue penetration. Furthermore, singlet oxygen should preferentially be generated without the incorporation of heavy atoms, as these often require additional synthetic efforts and/or afford dark cytotoxicity. Solutions for both problems are known, but have never been successfully combined in one simple BODIPY material. Here, we present a series of compact BODIPY-acridine dyads, active in the phototherapeutic window and showing balanced brightness and phototoxic power. Although the donor–acceptor design was envisioned to introduce a charge transfer state to assist in intersystem crossing, quantum-chemical calculations refute this. Further photophysical investigations suggest the presence of exciplex states and their involvement in singlet oxygen formation.
- Deckers, Jasper,Cardeynaels, Tom,Penxten, Huguette,Ethirajan, Anitha,Ameloot, Marcel,Kruk, Mikalai,Champagne, Beno?t,Maes, Wouter
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supporting information
p. 15212 - 15225
(2020/10/19)
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- Reductive Molybdenum-Catalyzed Direct Amination of Boronic Acids with Nitro Compounds
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The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C?N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. Moreover, this general and step-economical synthesis of aromatic secondary amines showcases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.
- Suárez-Pantiga, Samuel,Hernández-Ruiz, Raquel,Virumbrales, Cintia,Pedrosa, María R.,Sanz, Roberto
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supporting information
p. 2129 - 2133
(2019/01/25)
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- Nickel-catalyzed N-arylation of amines with arylboronic acids under open air
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In this study, a well-defined, novel NHC-Ni complex was developed and used to catalyze the N-arylation of alkyl- and arylamines with arylboronic acids in a rare version of Chan-Lam coupling. Although the same coupling using copper catalysts has been widely studied, the nickel-catalyzed version is rare and normally requires 10–20 mol% catalyst loading. This novel NHC-Ni complex in combination with 4,4′-dimethyl-2,2′-bipyridine, however, proved to be an effective catalyst that lowered the required catalyst loading to only 2.0 mol%.
- Ando, Shin,Hirota, Yurina,Matsunaga, Hirofumi,Ishizuka, Tadao
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supporting information
p. 1277 - 1280
(2019/04/10)
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- Syntheses of Acridones via Copper(II)-Mediated Relay Reactions from o-Aminoacetophenones and Arylboronic Acids
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The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O2 atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp3)-H amination, and C(sp2)-H activation with simultaneous rearrangement of the generated isatin intermediates. This strategy tolerates both electron-donating and -withdrawing functionalities to afford various acridones in good to excellent yields.
- Wu, Hao,Zhang, Zhiguo,Liu, Qingfeng,Liu, Tongxin,Ma, Nana,Zhang, Guisheng
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supporting information
p. 2897 - 2901
(2018/05/29)
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- N - aryl - hydrogel arc [tin [tin] light-emitting electroluminescent device as a component of
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wherein Ar is C3-C25 aryl in which at least one aromatic ring atom is nitrogen; X is O, S or CR9R10; R1, R2, R3, R4, R5 and R6 independently are hydrogen, deuterium, C1-C12 alkyl, C4-C12 aryl or C2-C12 alkenyl; R7 and R8 independently are hydrogen, deuterium, C1-C12 alkyl, C4-C12 aryl or C2-C12 alkenyl or R7 and R8 groups attached to a nitrogen atom are joined by a single bond, O, S or CR11R12 to form a single nitrogen-containing substituent; R9 and R10 independently are hydrogen, deuterium, C1-C12 alkyl, C4-C12 aryl or C2-C12 alkenyl; and R11 and R12 independently are hydrogen, deuterium, C1-C12 alkyl, C4-C12 aryl or C2-C12 alkenyl; provided that Ar does not contain an aromatic ring attached to the tricyclic nucleus which contains more than two aromatic ring nitrogen atoms.
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Paragraph 0043-0045
(2018/05/15)
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- Electroluminescent polymeric monomer, electroluminescent polymer as well as preparation method and application of electroluminescent polymer
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The invention belongs to the technical field of organic optoelectronics and discloses an electroluminescent polymeric monomer, an electroluminescent polymer as well as a preparation method and an application of the electroluminescent polymer. The structural formula of the polymeric monomer M1 is shown in the description, and the polymeric monomer M1 contains boron and nitrogen heteroatoms. Boron atoms have unoccupied Ppi orbit in the center and can accept electrons as Lewis acid, boron is in key joint with an aromatic ring substituent, P-pi conjugation is formed, the conjugation degree is increased, so that fluorescence of the monomer M1 is enhanced, and fluorescence quantum yield of a luminescent material is increased; the monomer M1 is endowed with better hole transport capability by a pair of lone pair electrons of nitrogen atoms. The monomer M1 is of a multi-condensed ring structure, and the carrier transport capability of the material can be improved by means of larger conjugate plane. The electroluminescent polymer contains repeat units derived from the electroluminescent polymeric monomer M1, has better solubility, can be dissolved with a common organic solvent and can forma film by spin coating, ink-jet printing or printing, and a luminescent layer of an LED is prepared.
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Paragraph 0048-0050
(2019/09/21)
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- ORGANIC COMPOUND, AND ORGANIC LIGHT-EMITTING DIODE AND ORGANIC LIGHT-EMITTING DIODE DISPLAY DEVICE INCLUDING THE SAME
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An organic compound is represented by the Formula below, and an organic light-emitting diode and an organic light-emitting diode display device include the organic compound.
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Paragraph 0109; 0110
(2018/06/29)
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- Structural design, synthesis and substituent effect of hydrazone-N-acylhydrazones reveal potent immunomodulatory agents
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4-(Nitrophenyl)hydrazone derivatives of N-acylhydrazone were synthesized and screened for suppress lymphocyte proliferation and nitrite inhibition in macrophages. Compared to an unsubstituted N-acylhydrazone, active compounds were identified within initial series when hydroxyl, chloride and nitro substituents were employed. Structure-activity relationship was further developed by varying the position of these substituents as well as attaching structurally-related substituents. Changing substituent position revealed a more promising compound series of anti-inflammatory agents. In contrast, an N-methyl group appended to the 4-(nitrophenyl)hydrazone moiety reduced activity. Anti-inflammatory activity of compounds is achieved by modulating IL-1β secretion and prostaglandin E2 synthesis in macrophages and by inhibiting calcineurin phosphatase activity in lymphocytes. Compound SintMed65 was advanced into an acute model of peritonitis in mice, where it inhibited the neutrophil infiltration after being orally administered. In summary, we demonstrated in great details the structural requirements and the underlying mechanism for anti-inflammatory activity of a new family of hydrazone-N-acylhydrazone, which may represent a valuable medicinal chemistry direction for the anti-inflammatory drug development in general.
- Meira, Cássio S.,dos Santos Filho, José Maurício,Sousa, Caroline C.,Anjos, Pamela S.,Cerqueira, Jéssica V.,Dias Neto, Humberto A.,da Silveira, Rafael G.,Russo, Helena M.,Wolfender, Jean-Luc,Queiroz, Emerson F.,Moreira, Diogo R.M.,Soares, Milena B.P.
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p. 1971 - 1985
(2018/03/12)
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- CARBAZOLE-BASED COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME
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This invention relates to a compound for an organic electroluminescent device represented by Chemical Formula 1 below and to an organic electroluminescent device including the same. The organic electroluminescent device including the compound is improved in thermal stability and light emission efficiency. When this compound is used as a hole transport layer material, the triplet energy of phosphorescent light emitting material in the organic electroluminescent device is increased, thus improving the efficiency of the organic electroluminescent device.
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Paragraph 0094; 0095
(2017/08/14)
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- CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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A condensed cyclic compound represented by Formula 1, comprising at least one cyano (—CN) group: wherein, in Formula 1, groups and variables are the same as described in the specification.
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Paragraph 0283; 0284; 0285
(2017/01/26)
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- CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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A condensed cyclic compound represented by Formula 1: wherein, in Formula 1, X1 to X8, X11 to X18, Y11, and Z11 to Z14 are the same as described in the specification.
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Paragraph 0324; 0325; 0326
(2017/02/24)
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- Use of a "catalytic" Cosolvent, N,N-Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch
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A general, efficient method for C-N cross-coupling has been developed using N,N-dimethyloctanamide as a catalytic cosolvent for biphasic continuous-flow applications. The described method was used to generate a variety of biarylamines and was integrated into a two-step sequence which converted phenols into biarylamines via either triflates or tosylates. Additionally, the method was applied to a three-step synthesis of imatinib, the API of Gleevec, in good yield without the need of solvent switches. Going with the flow: A general flow method developed for C-N cross-coupling using N,N-dimethyloctanamide as a catalytic cosolvent was integrated into a two-step sequence which converted phenols into biarylamines via either triflates or tosylates. It was applied to a three-step synthesis of imatinib, the API of Gleevec, in good yield without the need of solvent switches.
- Yang, Jeffrey C.,Niu, Dawen,Karsten, Bram P.,Lima, Fabio,Buchwald, Stephen L.
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p. 2531 - 2535
(2016/02/18)
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- COMPOUND, ORGANIC LIGHT EMITTING DIODE INCLUDING THE SAME AND DISPLAY INCLUDING THE ORGANIC LIGHT EMITTING DIODE
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The present invention relates to a compound, an organic light emitting diode including the same and a display device including the organic light emitting diode, which provides the compound for the organic photoelectron diode represented by chemical below formula 1.COPYRIGHT KIPO 2016
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Paragraph 0215; 0218; 0219
(2018/01/02)
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- Bifunctional AKR1C3 inhibitors/androgen receptor modulators and methods of use thereof
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The invention includes compositions comprising selective AKR1C3 inhibitors. The invention also includes compositions comprising bifunctional AKR1C3 inhibitors and selective androgen receptor modulators. The invention further includes methods of treatment using the compositions of the invention.
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Page/Page column 58; 59; 60
(2016/03/19)
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- An effective host material with thermally activated delayed fluorescence formed by confined conjugation for red phosphorescent organic light-emitting diodes
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A thermally activated delayed fluorescence material 2,6-bis(9,9-diphenylacridin-10(9H)-yl)pyrazine was designed and synthesized. The twisted configuration made it possesses very small singlet-triplet splitting. A red electroluminescent device based on thi
- Liu, Xiang-Yang,Liang, Feng,Yuan, Yi,Cui, Lin-Song,Jiang, Zuo-Quan,Liao, Liang-Sheng
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supporting information
p. 8149 - 8151
(2016/07/06)
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- Utilizing 9,10-dihydroacridine and pyrazine-containing donor-acceptor host materials for highly efficient red phosphorescent organic light-emitting diodes
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Two novel materials, 10-(6-(dibenzo[b,d]furan-1-yl)pyrazin-2-yl)-9,9-diphenyl-9,10-dihydroacridine (PrFPhAc) and 10-(6-(dibenzo[b,d]thiophen-1-yl)pyrazin-2-yl)-9,9-diphenyl-9,10-dihydroacridine (PrTPhAc), were designed and synthesized by introducing heter
- Liu, Xiang-Yang,Liang, Feng,Yuan, Yi,Jiang, Zuo-Quan,Liao, Liang-Sheng
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p. 7869 - 7874
(2016/09/04)
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- Delay fluorescent compound and using the same and display device having the organic light-emitting diode (by machine translation)
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The present invention provides a delay fluorescent compound and the use of the compound of the organic light-emitting diode and the display device, the delay fluorescent compound is a type 1 or type 2 delay fluorescent compound : [formula 1] ; [Formula 2] . (by machine translation)
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Paragraph 0101; 0102; 0103; 0104
(2016/10/08)
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- Effective host materials for blue/white organic light-emitting diodes by utilizing the twisted conjugation structure in 10-phenyl-9,10-dihydroacridine block
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Two new 10-phenyl-9,10-dihydroacridine derivatives attached by dibenzothiophene (DBT) and dibenzofuran (DBF) were synthesized. The influence of the substituents of these materials was studied by theoretical calculations (DFT calculation) and experimental
- Liu, Xiang-Yang,Liang, Feng,Cui, Lin-Song,Yuan, Xiao-Dong,Jiang, Zuo-Quan,Liao, Liang-Sheng
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p. 1402 - 1409
(2015/06/08)
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- Construction of 1,4-benzodiazepine skeleton from 2-(arylamino)benzamides through PhI(OAc)2-mediated oxidative C-N bond formation
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New compounds involving the biologically important 1,4-benzodiazepine skeleton were conveniently constructed from 2-(arylamino)benzamides through PhI(OAc)2-mediated oxidative C-N bond formation. The attractive features of this new synthetic strategy include mild reaction conditions, the heavy-metal-free characteristic of the oxidative coupling process, and the flexibility to tolerate a broad scope of substrates.
- Li, Xuming,Yang, Liu,Zhang, Xiang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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p. 955 - 962
(2014/03/21)
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- MODULATION OF K2P CHANNELS
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Disclosed herein inter alia are compositions and methods useful in the treatment of diseases, for example pain, neurodegeneration, or mood disorders, and for modulating the activity of a K2P channel.
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Paragraph 0314
(2014/10/18)
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- SPIROBIFLUORENE COMPOUNDS FOR LIGHT EMITTING DEVICES
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Novel spirobifluorene compounds for light emitting devices where the spirobifluorene ring system comprises at least one acridine-type substituent.
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Paragraph 0097
(2013/04/13)
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- Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N -phenyl-aminobenzoates and their structure-activity relationships
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Aldo-keto reductase 1C3 (AKR1C3; type 5 17β-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5α-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of 5α-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.
- Adeniji, Adegoke O.,Twenter, Barry M.,Byrns, Michael C.,Jin, Yi,Chen, Mo,Winkler, Jeffrey D.,Penning, Trevor M.
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supporting information; experimental part
p. 2311 - 2323
(2012/05/04)
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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Organic electroluminescent compounds comprising a triphenylene conjugated to a five-ring fused heterocyclic system, as depicted in formula 1 are provided. Also provided is an organic electroluminescent device comprising these compounds. The organic electroluminescent compounds disclosed herein exhibit good luminous efficiency and excellent material life. They can be used to manufacture OLED devices very superior in terms of operating life and which consume less power due to improved power efficiency.
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Page/Page column 23
(2012/04/10)
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- Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17β-hydroxysteroid dehydrogenase (AKR1C3)
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Aldo-keto reductase 1C3 (AKR1C3) also known as type 5 17β- hydroxysteroid dehydrogenase has been implicated as one of the key enzymes driving the elevated intratumoral androgen levels observed in castrate resistant prostate cancer (CRPC). AKR1C3 inhibition therefore presents a rational approach to managing CRPC. Inhibitors should be selective for AKR1C3 over other AKR1C enzymes involved in androgen metabolism. We have synthesized 2-, 3-, and 4-(phenylamino)benzoic acids and identified 3-(phenylamino)benzoic acids that have nanomolar affinity and exhibit over 200-fold selectivity for AKR1C3 versus other AKR1C isoforms. The AKR1C3 inhibitory potency of the 4′-substituted 3-(phenylamino)benzoic acids shows a linear correlation with both electronic effects of substituents and the pKa of the carboxylic acid and secondary amine groups, which are interdependent. These compounds may be useful in treatment and/or prevention of CRPC as well as understanding the role of AKR1C3 in endocrinology.
- Adeniji, Adegoke O.,Twenter, Barry M.,Byrns, Michael C.,Jin, Yi,Winkler, Jeffrey D.,Penning, Trevor M.
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supporting information; experimental part
p. 1464 - 1468
(2011/04/16)
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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Provided are organic electroluminescent compounds of a fused pentacyclic structure of general formula I, and an organic electroluminescent device using said compounds. Since the organic electroluminescent compounds exhibit good luminous efficiency and lifespan, they may be used to manufacture OLED devices which have a superior operational lifetime and also have low power consumption due to the improved power efficiency of the compounds.
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Page/Page column 15
(2011/08/21)
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- Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: Synthesis and mechanistic study
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(Chemical Equation Presented) An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.
- Watanabe, Toshiaki,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
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experimental part
p. 4720 - 4726
(2009/10/02)
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- NOVEL ANTHRANILIC ACID DERIVATIVES AND CHLORIDE CHANNEL BLOCKING AGENT CONTAINING THE SAME
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The present invention relates to novel anthranilic acid derivatives represented by Chemical Formula I, and a chloride channel blocking agent containing the anthranilic acid derivative or its pharmacologically acceptable salts as an active ingredient. In another aspect, the present invention relates to a method of accurately and efficiently detecting the intracellular chloride channel inhibition and method of screening a chloride channel blocking agent.
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Page/Page column 6
(2009/05/28)
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- Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates
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The reaction of silylaryl triflates, CsF, and ortho-heteroatom-substituted benzoates affords a general and efficient way to prepare biologically interesting xanthones, thioxanthones, and acridones. This chemistry presumably proceeds by a tandem intermolecular nucleophilic coupling of the benzoate with an aryne and a subsequent intramolecular electrophilic cyclization.
- Zhao, Jian,Larock, Richard C.
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p. 583 - 588
(2007/10/03)
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- Synthesis and through-bond spin interaction of stable 1,3-phenylene-linked polyradical carrying aminoxyls in the π-conjugated main chain
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A stable polyradical carrying aminoxyls in the π-conjugated main chain was synthesized and its through-bond spin interaction was investigated. The polyradical is constructed with 1,3-phenylene as a spin coupler and 9,9-di-n-propyl-9,10-dihydroacridin-10-yloxy as a stable spin source. The synthetic method of the spin source moiety was modified by using conventional organic reactions from a previously reported method. The polymeric structure was synthesized by Suzuki-Miyaura coupling. The degree of polymerization and the spin concentration of the polyradical were ca. 11 and 0.71 spins per repeating unit, respectively, indicating that there were ca. 8 spins per molecule. The average S value of the polyradical was 3/2, therefore, 3 spins out of 8 spins were aligned in the polyradical. This showed that the through-bond spin interaction occurs more effectively than in our previous polyradical carrying aminoxyls in the side chain. The Royal Society of Chemistry 2007.
- Oka, Hiroyuki,Kouno, Hiroshi,Tanaka, Hitoshi
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p. 1209 - 1215
(2008/02/05)
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- An advantageous synthesis of new indazolone and pyrazolone derivatives
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The synthesis of new indazolone and pyrazolone derivatives starting from methyl anthranilate type substrates is presented. This general approach constitutes a novel and advantageous alternative for the synthesis of the target heterocycles, which implies the use of the environmentally friendly oxidizer PIFA. The synthetic design includes the oxidation of N-arylamides by the hypervalent iodine reagent to the corresponding N-acylnitrenium ions, which can be intramolecularly trapped by an amine moiety to furnish the title compounds by formation of a new N-N single bond.
- Correa, Arkaitz,Tellitu, Imanol,Domínguez, Esther,SanMartin, Raul
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p. 11100 - 11105
(2007/10/03)
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- A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester
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A new and readily available bidentate ligand, namely, pyrrolidine-2- phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.
- Rao, Honghua,Jin, Ying,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 3636 - 3646
(2008/02/03)
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- Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2- phosphonate as the new ligand
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We have developed a general, efficient, and inexpensive catalyst system for arylation of amines by using 10 mol % of CuI as the copper source, 20 mol % of diphenyl pyrrolidine-2-phosphonate (DPP) as the ligand, K3PO 4 as the base, and DMF containing 2% water (v/v) as the solvent.
- Rao, Honghua,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 8107 - 8109
(2007/10/03)
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- A survey on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4- naphthoquinone with amino compounds
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The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield.
- Spagou, Konstantina,Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros
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p. 226 - 237
(2007/10/03)
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- Palladium-Catalyzed Amination of Aryl Nonaflates
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The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands 2-4 and 6 allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos 5, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions.
- Anderson, Kevin W.,Mendez-Perez, Maria,Priego, Julian,Buchwald, Stephen L.
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p. 9563 - 9573
(2007/10/03)
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- 3-piperidyl-4-oxoquinazoline derivatives and pharmaceutical compositions comprising the same
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3-piperidyl-4-oxoquinazoline derivatives are provided, which is represented by the formula (I): wherein R represents an amino group or a cyclic amino group such as dibenzoazepine, each of which is substituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the like, n is an integer of 1 to 3, R3and R4independently represents a hydrogen atom, a lower alkyl group, or the like, or a pharmaceutically acceptable salt thereof. Compounds (I) of the present invention have excellent MTP-inhibitory activity. Thus, these compounds not only inhibit formation of LDL that is a cause of arteriosclerotic diseases but also regulate TG, cholesterol, and lipoproteins such as LDL in the blood and regulate cellular lipids through regulation of MTP activity. They can also be used as a new type of preventive or therapeutic agents for hyperlipemia or arteriosclerotic diseases. Furthermore, they can be used as therapeutic or preventive agents for pancreatitis, obesity, hypercholesterolemia, and hypertriglyceridemia.
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- Formation of aryl-nitrogen bonds using a soluble copper(I) catalyst
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We report a synthetic protocol for the synthesis of functionalized diaryl- and triarylamines under mild conditions, using a soluble, air-stable copper(I) complex, Cu(PPh3)3Br, as the catalyst and cesium carbonate as the base. Using this protocol, we were able to synthesize a tri-ortho-ester functionalized triphenylamine, which had eluded us using the palladium chemistry.
- Gujadhur, Rattan,Venkataraman,Kintigh, Jeremy T
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p. 4791 - 4793
(2007/10/03)
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- 12-Organyldibenzazocine-5,7-diones
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The title compounds 10, 23 are formed in low yields on treatment of 2,2'-organylimino-bisbenzoic acid esters 8 with methyllithium, but in high yields in the intramolecular ester condensation with sodium hydride of triarylamines 12, containing o-acetyl-, a
- Hellwinkel, Dieter,Ittemann, Peter
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p. 3165 - 3197
(2007/10/02)
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- Diphenylamino and indolyl substituted pyromellitides
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This invention relates to 3,7-bis(disubstituted aminophenyl- or indolyl)-3,7-bis(diphenylamino)pyromellitides, 3,5-bis(disubstituted aminophenyl- or indolyl)-3,5-bis(diphenylamino)pyromellitides and mixtures thereof useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared by the interaction of 2,5-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,4-benzenedicarboxylic acids or 2,4-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,5-benzenedicarboxylic acids and mixtures thereof with diphenylamines.
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