- Synthesis and photophysical properties of a series of thermally stable terphenyl-bridged bisbenzimidazoles
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Nine novel terphenyl-bridged bisbenzimidazoles were synthesized in high yield by the condensation of o-phenylenediamines and terphenyl dinitriles in the presence of polyphosphoric acid. The bisbenzimidazoles are thermally robust with high decomposition te
- Luo, Zhonghua,Zhu, Hongjun,Song, Guangliang,Chang, Jin,Liu, Rui
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- Lithium aminoborohydrides 17. Palladium catalyzed borylation of aryl iodides, bromides, and triflates with diisopropylaminoborane prepared from lithium diisopropylaminoborohydride
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The Alcaraz-Vaultier borylation of aryl halides and triflates is reported utilizing diisopropylaminoborane (BH2N(iPr)2) prepared from the corresponding lithium aminoborohydride (LAB reagent). BH 2N(iPr)2, prepared by reacting lithium diisopropylaminoborohydride with trimethylsilyl chloride, provided the most consistent isolated yields from this reaction. Catalytic amounts of palladium dichloride produced the highest yields from aryl iodides, while catalytic tris(dibenzylideneacetone)dipalladium(chloroform) provided the best yields for aryl bromides and triflates. This route to boronic acids is mild enough to tolerate various functionalities and for the first time employs aryl triflates as substrates for the Alcaraz-Vaultier borylation. In addition, it was found that both boronic acid and ester compounds could be isolated from the reaction mixture utilizing simple work-up procedures. Treatment of the reaction intermediate with an acid/base work-up provided the corresponding boronic acid, while treating the same intermediate with a diol, such as neopentyl glycol, afforded the corresponding boronic ester.
- Haddenham, Dustin,Bailey, Christopher L.,Vu, Chau,Nepomuceno, Gabby,Eagon, Scott,Pasumansky, Lubov,Singaram, Bakthan
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Read Online
- Triarylamine-based dual-function coadsorbents with extended π-conjugation aryl linkers for organic dye-sensitized solar cells
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Triarylamine-based dual-function coadsorbents containing a carboxylic acid acceptor linked by extended π-conjugation aryl linkers (e.g., phenylene: HC-A3, naphthalene: HC-A4 and anthracene: HC-A5) were newly designed and synthesized. They were used as coadsorbents in organic dye-sensitized solar cells (DSSCs) based on a porphyrin dye (hexyloxy-biphenyl-ZnP-CN-COOH (HOP)). For comparison, the π-conjugated phenyl linker (HC-A3) previously developed by our group was also used as a coadsorbent. The structural effects on the photophysical and electrochemical properties and DSSC performance were systematically investigated. As a result, the DSSCs based on HC-A4 and HC-5 displayed power conversion efficiencies (PCEs) of 8.2% and 5.1%, respectively, while the HC-A3-based DSSC achieved a PCE of 7.7%. In the case of HC-A4, both the short-circuit photocurrent densities (Jsc) and open-circuit voltages (Voc) of DSSCs were simultaneously improved to a large extent due to the more effective prevention of π-π stacking of organic dye molecules and the better light-harvesting effect at short wavelengths. The HC-A5-based DSSC exhibited a much lower short-circuit current (Jsc) and open-circuit voltages (Voc) compared to the HC-A4-based DSSC, due to the fact that the dihedral angle of the π-conjugated linkers was too high for electron injection into the TiO2 conduction band (CB) level. This had a reduced effect on preventing the π-π stacking of dye molecules, resulting in lower Jsc and Voc values.
- Choi, In Taek,You, Ban Seok,Eom, Yu Kyung,Ju, Myung Jong,Choi, Won Seok,Kang, Sung Ho,Kang, Min Soo,Seo, Kang Deuk,Hong, Ji Yeoun,Song, Sang Hyun,Yang, Ji-Woon,Kim, Hwan Kyu
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Read Online
- Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges
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A general and convenient protocol for the electrophilic borylation of aryl Grignard reagents prepared from arylbromides by direct insertion of magnesium in the presence of LiCl or by Mg/Br exchange with iPrMgCl?LiCl has been developed. Various aryl boronic acids were synthesized in a straightforward manner in excellent yields at 0 °C.
- Leermann, Timo,Leroux, Frederic R.,Colobert, Francoise
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Read Online
- Synthesis and thermal analysis of disubstituted propiolates bearing terphenylene mesogen
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Novel disubstituted propiolates bearing chromophoric terphenylene mesogenic groups, namely, 40-cyano- 4-terphenylyl-2-octynate M(CN) and 40-methoxyl-4-terphenylyl- 2-octynate M(OCH3) are synthesized, where the terphenyl groups are connected to the C≡C through ester linkage directly. Using transition-metal catalysts such as the classical MoCl 5- and WCl6-based metathesis catalysts, the polymerization of the M(CN) and M(OCH3) are carried out in a series of different solution, however, did not obtain any products. It suggests that the WCl 6- and MoCl5-based catalysts are poisoned by the polar groups, on the other hand, the bulk terphenyl groups and the long alkyl chain around the C≡C bond might inhibit the reaction. M(CN) displays monotropic nematicity, whereas M(OCH3) exhibits enantiotropic nematicity and smecticity (SmAd) with a bilayer arrangement when cooled and heated. Ultraviolet spectroscopy and photoluminescence measurements also show that the terphenyl groups endow disubstituted propiolates with strong UV light absorption and high photoluminescence. Akademiai Kiado, Budapest, Hungary 2009.
- Chen, Lie,Chen, Yiwang,Zhou, Weihua,He, Xiaohui,Song, Yanlin,Zhang, Zhijie
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Read Online
- Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source
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In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.
- Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup
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p. 10966 - 10972
(2020/09/23)
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- Nimesulide derivatives and preparation method and application thereof
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The invention relates to a preparation method of four nimesulide derivatives with the function of treating liver malignant tumors. According to the invention, a nimesulide solution and an acid or alkaline substance are subjected to displacement reaction to generate three salts with better water solubility and more stability, which are the nimesulide derivatives, or p-aminobenzonitrile is used as asubstrate, the fourth nimesulide derivative with higher bioavailability is generated through a series of redox reactions, four novel nimesulide derivatives are successfully prepared, all the four compounds are soluble in water, the solubility is better than that of the nimesulide, and better absorption rate and bioavailability are provided, and the hepatotoxicity of the four derivatives is not obviously different from that of the nimesulide at normal dose, and only one derivative is enhanced in liver toxicity at overdose. The inhibitory effect on BEL-7402 is no less than or even stronger thanthat of nimesulide when the four derivatives are co-cultured with CIK cells. The four nimesulide derivatives can be used for preparing drugs for inhibiting human liver cancer cells.
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Page/Page column 13-15; 17-19; 21-22
(2019/04/26)
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- Synthesis and evaluation of sulfonamide derivatives as potent Human Uric Acid Transporter 1 (hURAT1) inhibitors
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This letter presents synthesis and structure-activity relationship study of sulfonamide derivatives as inhibitors of Human Uric Acid Transporter 1 (hURAT1). Among all tested sulfonamide derivatives, compounds 9b, 16i and 19b exhibited excellent inhibition activity with IC50 value of 10, 2, and 83?nM, respectively. In addition, compounds 9b and 19b demonstrated moderate PK profile in rats.
- Yang, Xintuo,Pang, Xuehai,Fan, Lei,Li, Xinghai,Chen, Yuanwei
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supporting information
p. 1919 - 1922
(2017/04/10)
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- Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure
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The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.
- Smith, Michael J.,Lawler, Michael J.,Kopp, Nathaniel,McLeod, Douglas D.,Davulcu, Akin H.,Lin, Dong,Katipally, Kishta,Sfouggatakis, Chris
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p. 1859 - 1863
(2017/11/24)
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- Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
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A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.
- Chen, Kai,Zhang, Shuai,He, Pei,Li, Pengfei
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p. 3676 - 3680
(2016/06/09)
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- Spectroscopic and computational investigations of the thermodynamics of boronate ester and diazaborole self-assembly
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The solution phase self-assembly of boronate esters, diazaboroles, oxathiaboroles, and dithiaboroles from the condensation of arylboronic acids with aromatic diol, diamine, hydroxythiol, and dithiol compounds in chloroform has been investigated by 1H NMR spectroscopy and computational methods. Six arylboronic acids were included in the investigations with each boronic acid varying in the substituent at its 4-position. Both computational and experimental results show that the para-substituent of the arylboronic acid does not significantly influence the favorability of forming a condensation product with a given organic donor. The type of donor, however, greatly influences the favorability of self-assembly. 1H NMR spectroscopy indicates that condensation reactions between arylboronic acids and catechol to give boronate esters are the most favored thermodynamically, followed by diazaborole formation. Computational investigations support this conclusion. Neither oxathiaboroles nor dithiaboroles form spontaneously at equilibrium in chloroform at room temperature. Computational results suggest that the effect of borylation on the frontier orbitals of each donor helps to explain differences in the favorability of their condensation reactions with arylboronic acids. The results can inform the use of boronic acids as they are increasingly utilized in the dynamic self-assembly of organic materials and as components in dynamic combinatorial libraries.
- Goldberg, Alexander R.,Northrop, Brian H.
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p. 969 - 980
(2016/02/18)
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- Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts
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We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.
- Mfuh, Adelphe M.,Doyle, John D.,Chhetri, Bhuwan,Arman, Hadi D.,Larionov, Oleg V.
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supporting information
p. 2985 - 2988
(2016/03/19)
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- An easy route to (hetero)arylboronic acids
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An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.
- Erb, William,Hellal, Akila,Albini, Mathieu,Rouden, Jacques,Blanchet, Jerome
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p. 6608 - 6612
(2014/06/09)
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- Sequential one-pot access to molecular diversity through aniline aqueous borylation
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On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.
- Erb, William,Albini, Mathieu,Rouden, Jacques,Blanchet, Jrme
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p. 10568 - 10580
(2015/01/08)
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- Enthalpy-entropy compensation combined with cohesive free-energy densities for tuning the melting temperatures of cyanobiphenyl derivatives
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This work illustrates how minor structural perturbations produced by methylation of 4′-(dodecyloxy)-4-cyanobiphenyl leads to enthalpy-entropy compensation for their melting processes, a trend which can be analyzed within the frame of a simple intermolecular cohesive model. The transformation of the melting thermodynamic parameters collected at variable temperatures into cohesive free-energy densities expressed at a common reference temperature results in a novel linear correlation, from which melting temperatures can be simply predicted from molecular volumes. In tune with temperature! The transformation of the melting thermodynamic parameters into cohesive free-energy densities (CFED) for 4′-(n-oxy)-i′-methyl-j-methyl-4-cyanobiphenyl (CnLi′,j) provides a novel linear correlation for predicting melting temperatures in a simple way. Copyright
- Dutronc, Thibault,Terazzi, Emmanuel,Guenee, Laure,Buchwalder, Kerry-Lee,Spoerri, Aurore,Emery, Daniel,Mareda, Jiri,Floquet, Sebastien,Piguet, Claude
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supporting information
p. 8447 - 8456
(2013/07/19)
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- Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]
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Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.
- Molander, Gary A.,Cavalcanti, Livia N.,Garcia-Garcia, Carolina
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p. 6427 - 6439
(2013/07/26)
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- Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid
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The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.
- Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.,Dreher, Spencer D.,Tudge, Matthew T.
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supporting information; experimental part
p. 11667 - 11673
(2012/09/05)
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- Wavelength conversion lanthanide(III)-cored complex for highly efficient dye-sensitized solar cells
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Lanthanide(III)-cored complex as a wavelength conversion material has been successfully designed and synthesized for highly efficient dye-sensitized solar cells, for the first time, since light with a short wavelength has not been effectively used for generating electric power owing to the limited absorption of these DSSCs in the UV region. A black dye (BD) was chosen and used as a sensitizer, because BD has a relatively weak light absorption at shorter wavelengths. The overall conversion efficiency of the BD/WCM device was remarkably increased, even with the relatively small amount of WCM added to the device. The enhancement in Voc by WCM, like DCA, could be correlated with the suppression of electron recombination between the injected electrons and I3 - ions. Furthermore, the short-circuit current density was significantly increased by WCM with a strong UV light-harvesting effect. The energy transfer from the Eu(III)-cored complex to the TiO2 film occurred via the dye, so the number of electrons injected into the TiO2 surface increased, i.e., the short-circuit current density was increased. As a result, BD/WCM-sensitized solar cells exhibit superior device performance with the enhanced conversion efficiency by a factor of 1.22 under AM 1.5 sunlight: The photovoltaic performance of the BD/WCM-based DSSC exhibited remarkably high values, Jsc of 17.72 mA/cm2, Voc of 720 mV, and a conversion efficiency of 9.28% at 100 mW cm-2, compared to a standard DSSC with Jsc of 15.53 mA/cm2, Voc of 689 mV, and a conversion efficiency of 7.58% at 100 mW cm-2. Therefore, the Eu(III)-cored complex is a promising candidate as a new wavelength conversion coadsorbent for highly efficient dyesensitized solar cells to improve UV light harvesting through energy transfer processes. The abstract should be a single paragraph which summaries the content of the article.
- Oh, Jung Hwan,Song, Hae Min,Eom, Yu Kyung,Ryu, Jung Ho,Ju, Myung Jong,Kim, Hwan Kyu
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scheme or table
p. 2743 - 2750
(2012/02/01)
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- Effects of substitution and terminal groups for liquid-crystallinity enhanced luminescence of disubstituted polyacetylenes carrying chromophoric terphenyl pendants
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Liquid-crystalline and light-emitting poly(2-alkyne)s containing terphenyl cores with hexamethyleneoxy spacers, and cyano or n-propoxy tails - [CH3C=C(CH2)6O-terphenyl-R] n -, where R=CN, CH3PA6CN, R=OCH2CH 2CH3, CH3PA6OPr, were synthesized. The effects of the substitution and terminal groups on the properties, especially the mesomorphic and optical properties of the polymers, were investigated. The disubstituted acetylene monomers (CH3A6CN, CH3A6OPr) were prepared through multistep reaction routes and were polymerized by WCl6-Ph4Sn in good yields (up to 82%). All the monomers and CH3PA6CN exhibited the enantiotropic SmA phase with a monolayer arrangement at elevated temperatures, whereas CH3PA6OPr formed a bilayer SmAd packing arrangement. Upon excitation at 330 nm, strong UV and blue emission peaks at 362 and 411 nm were observed in CH3PA6OPr and CH3PA6CN, respectively. The luminescent properties of CH3PA6CN and CH3PA6OPr have been improved by introducing the methyl substituted group, and the quantum yield of the polymer with cyano tail CH3PA6CN (Φ = 74%) was found to be higher than that of CH3PA6OPr (Φ = 60%). Compared to polyacetylene parents, both CH3PA6OPr and CH3PA6CN showed a narrower energy gap. This demonstrated that the electrical conductivities of polyacetylenes could be enhanced by attaching appropriate pendants to the conjugated polyene backbones.
- Zhou, Dan,Chen, Yiwang,Chen, Lie,Li, Fan,Nie, Huarong,Yao, Kai
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experimental part
p. 1302 - 1315
(2010/11/05)
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- Base free aryl coupling of diazonium compounds and boronic esters: Self-activation allowing an overall highly practical process
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Boronic esters have long been considered as poor partners in cross-coupling reactions with arene diazoniums. Here is reported an unprecedented application of self-activated boronic esters in a base-free cross-coupling reaction with diazonium salts under mild and user friendly conditions.
- Bonin, Helene,Delbrayelle, Dominique,Demonchaux, Patrice,Gras, Emmanuel
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supporting information; experimental part
p. 2677 - 2679
(2010/07/08)
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- Synthesis and properties of light-emitting polythiophene derivatives bearing terphenyl mesogenic pendant
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A series of polythiophenes containing terphenyl mesogenic side chain at the third position through ester bonding was synthesized by dehalogenative polycondensation. The thiophene monomers 2,5-bromo-3-{[(4-(4'-cyano) terphenyloxy)carbonyl]-methyl]}-thiophene [M(CN)] and 2,5-bromo-3-{[(4-(4'- methoxy)terphenyloxy)-carbonyl]methyl}-thiophene [M(OCH3)] were prepared via Suzuki reation and esterification reactions, in sequence. The structures and properties of the monomers and polymers were characterized and evaluated with nuclear magnetic resonance, infrared spectroscopy, thermogravimetry, differential scanning calorimetry, polarized optical microscopy, ultraviolet spectroscopy, and photoluminescence. All of the polymers were stable, losing little of their weights when heated to 300°C. The polymers showed good solubility and could be dissolved in common solvents such as CHCl3, THF, DMF, etc. The monomers exhibited enantiotropic SmAd phases with a bilayer arrangement in the heating and cooling processes. Due to short spacer methylene ester between the bulk terphenyl mesogenic side chain and rigid polythiophene main chain, the polymers could not exhibit liquid crystallinty at elevated temperature. The existence of the chromophoric terphenyl core endows the polymers with high photoluminescence. When their CH2Cl2 solutions were photoexcited, the polymers emitted a strong UV light about 400nm.
- Chen, Lie,Chen, Yiwang,Zhou, Weihua,Li, Fan,He, Xiaohui,Tang, Ben Zhong
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experimental part
p. 70 - 83
(2011/05/03)
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- Efficient hydrolysis of organotrifluoroborates via silica gel and water
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(Chemical Equation Presented) A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H2O was developed. This method proved to be tolerant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structurally diverse aminomethylated organotrifluoroborates.As anticipated, electron-rich substrates provided the corresponding boronic acids more readily than electron-poor substrates, owing to the resonance-stabilized difluoroborane intermediate. The method developed was expanded further for the conversion of organotrifluoroborates to the corresponding boronate esters. 2009 American Chemical Society.
- Molander, Gary A.,Cavalcanti, Livia N.,Canturk, Belgin,Pan, Po-Shen,Kennedy, Lauren E.
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supporting information; experimental part
p. 7364 - 7369
(2010/01/16)
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- Substituent effects on aryltrifluoroborate solvolysis in water: Implications for Suzuki-Miyaura coupling and the design of stable 18F-labeled aryltrifluoroborates for use in PET imaging
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(Chemical Equation Presented) Whereas electron withdrawing substituents retard the rate of aryltrifluoroborate solvolysis, electron-donating groups enhance it. Herein is presented a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log(Ksolv) values correlate to a values with a ρ value of approximately -1. This work provides a predictable rubric for tuning the reactivity of boron for several uses including 18F-labeled PET reagents and has mechanistic implications for ArBF3-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.
- Ting, Richard,Harwig, Curtis W.,Lo, Justin,Li, Ying,Adam, Michael J.,Ruth, Thomas J.,Petrin, David M.
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p. 4662 - 4670
(2008/09/20)
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- Mild and general methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides
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New methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides have been developed, featuring sterically demanding, electron-rich phosphines. Highly challenging electron-rich aryl chlorides, in addition to electron-neutral and electron-deficient substrates, as well as nitrogen- and sulfur-containing heteroaryl chlorides can all undergo efficient cyanation under relatively mild conditions using readily available materials. In terms of substrate scope and temperature, these methods compare very favorably with the state-of-the-art cyanations of aryl chlorides.
- Littke, Adam,Soumeillant, Maxime,Kaltenbach III, Robert F.,Cherney, Robert J.,Tarby, Christine M.,Kiau, Susanne
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p. 1711 - 1714
(2008/02/02)
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- Monofluoroalkyl derivatives
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The present invention provides certain monofluoroalkyl derivatives useful for potentiating glutamate receptor function in a mammal and therefore, useful for treating a wide variety of conditions, such as psychiatric and neurological disorders.
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Page/Page column 37
(2010/10/20)
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- BICYCLIC COMPOUNDS
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The present invention is to provide a bicyclic compound represented by the following formula: wherein Ring Q is pyridine or pyrimidine; Ring A is benzene or a heterocyclic ring; G is Ring B optionally having a substituent(s) R3, or an amino optionally substituted by one or two selected from the group consisting of alkyl(s), aralkyl(s) and cycloalkyl(s); Ring B is benzene, a heterocyclic ring, a cycloalkane or a cycloalkene; R1 is a group selected from the following formulae: R2 and R3 may be the same or different from each other, and each is cyano, nitro, etc.; m is 0, 1 or 2; R4 is hydrogen, a halogen, etc.; and R5 and R6 may be the same or different from each other, and each is hydrogen, an optionally substituted alkyl, etc., or a pharmaceutically acceptable salt thereof, which is a large conductance calcium-activated K channel opener useful for treatment of pollakiuria, urinary incontinence, etc.
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(2010/02/14)
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- Benzoxepin-derived estrogen receptor modulators: A novel molecular scaffold for the estrogen receptor
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We present and examine the efficacy of a novel benzoxepin-based scaffold for modulation of the human estrogen receptor. Receptor tolerance of this new molecular scaffold is examined through presentation of experimentally determined antiproliferative effects on human MCF-7 breast tumor cells and measured binding affinities. The effect of functional group substitution on the benzoxepin scaffold is explored through a brief computational structure - activity relationship investigation with molecular simulation.
- Lloyd, David G.,Hughes, Rosario B.,Zisterer, Daniela M.,Williams, D. Clive,Fattorusso, Caterina,Catalanotti, Bruno,Campiani, Giuseppe,Meegan, Mary J.
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p. 5612 - 5615
(2007/10/03)
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- Potentiators of glutamate receptors
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The present invention relates to potentiators of metabotropic glutamate receptor function and specifically provides compounds of formula I, compositions thereof and methods of using the same.
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- Synthesis of 4,5-diarylquinazolines: A system with cofacial aromatic rings. Diazines. Part 39
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Using metallation reactions and Pd-catalyzed coupling, we report here two synthetic routes leading to eight new 4,5-di(hetero)arylquinazolines. Non-linear activity has been highlighted for some of these compounds with stacked aromatic rings.
- Busch, Alexandrine,Chapoulaud, Valérie Gautheron,Audoux, Jér?me,Plé, Nelly,Turck, Alain
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p. 5373 - 5382
(2007/10/03)
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- 5-Phenyl[1,2,4]triazines as ligands for GABA-A alpha2/alpha3 receptors for treating anxiety or depression
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The present invention provides a compound of formula I, or an N-oxide thereof or a pharmaceutically acceptable salt thereof: wherein X1 represents hydrogen, halogen, C1-6 alkyl, trifluoromethyl or C1-6 alkoxy; X2 represents hydrogen or halogen; Z represents hydrogen, halogen, cyano, cyanomethyl, trifluoromethyl, nitro, hydroxy, hydroxy(C1-6)alkyl, C1-6 alkoxy, C1-6 alkoxy(C1-6)alkyl, trifluoromethoxy, trifluoromethylthio, trifluoromethanesulfinyl, formyl, C2-6 alkoxycarbonyl, oxopyrrolidinyl, or an optionally substituted aryl, heteroaryl or heteroaryl(C1-6)alkoxy group; and R1 represents aryl or heteroaryl, either of which groups may be optionally substituted; pharmaceutical compositions comprising it, its use in therapy and methods of treatment of anxiety and/or depression using it.
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- Sulfonamide derivatives
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The present invention provides certain sulfonamide derivatives useful for potentiating glutamate receptor function in a patient and therefore, useful for treating a wide variety of conditions, such as psychiatric and neurological disorders.
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- Tetraphenylethene-derived columnar liquid crystals and their oxidative photocyclization
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The synthesis of novel tetraphenylethenes 9a-f, 13, and 18a,b bearing ether, biphenyl, and 4-cyanobiphenyl moieties via a McMurry reaction and Suzuki coupling as key steps is described. Mesogenic properties of these compounds were studied by differential
- Schultz, Andreas,Laschat, Sabine,Diele, Siegmar,Nimtz, Manfred
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p. 2829 - 2839
(2007/10/03)
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- Process for the preparation of substituted phenylboronic acids
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Compounds of the formula (I) in which Q1and Q2are each OH or form a trimeric boric anhydride, Z is CHO, CH2Y, X or a protected aldehyde group, and X is CN, COOH, COCl, CONH2or C(OR)3, and Y is OH or NH2, and Z is in the o-, m- or p-position to the boronic acid radical, are prepared by a) reacting a compound of the formula (II) ?with Mg in the presence of an anthracene compound and, if desired, a transition-metal halide and, if desired, an Mg halide or in the presence of a transition-metal halide and, if desired, an Mg halide, to give the corresponding arylmagnesium chloride, b) reacting the latter with a borate of the formula B(OR′)3and hydrolyzing the product, with removal of the aldehyde protecting group, c) and, if desired, oxidizing or reducing the free aldehyde group.
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- 3,3-disubstituted-oxindole derivatives useful as anticancer agents
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The present invention relates to compounds of formula 1 and to pharmaceutically acceptable salts, prodrugs, and solvates thereof, wherein n is 0 or 1 and R1, R2, R3, R4, and R5are as defined herein. The above compounds of formula 1 are useful in the treatment of hyperproliferative disorders, such as cancer, in mammals. The invention also relates to pharmaceutical compositions containing the compounds of formula 1, to methods of inhibiting abnormal cell growth, including cancer, in a mammal by administering the compounds of formula 1 to a mammal requiring such treatment, and to methods of preparing compounds of formula 1.
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- Sulfonamide derivatives
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The present invention provides certain sulfonamide derivatives useful for potentiating glutamate receptor function in a mammal and therefore, useful for treating a wide variety of conditions, such as psychiatric and neurological disorders.
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- Synthesis and liquid crystal phase behaviour of 2-(4-cyanophenyl)-7-n-alkylfluorenes: Luminescent mesogens
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A new range of nematic liquid crystals containing the 2-phenylfluorene core has been prepared which may be considered as a model system for luminescent mesogens, which have potential interest as new display materials.
- Boardman, Frederick H.,Dunmur, David A.,Grossel, Martin C.,Luckhurst, Geoffrey R.
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- Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands
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Hydrophilic phosphine ligands possessing a carbohydrate side-chain, such as N-(4-diphenylphosphinophenyl)methyl gluconamide (9), N-[4-(2′-dicyclohexylphosphinobiphenyl)phenylmethyl] gluconamide (10), and N-[4-(2′-di-t-butylphosphinobiphenyl)]phenylmethyl gluconamide (11), were newly synthesized to carry out palladium-catalyzed biaryl coupling of arylboronic acids in a single aqueous medium. The catalyst prepared in situ from Pd(OAc)2 and 10 exhibited a higher efficiency than that of 9, 11, Ph2P(m-C6H4SO3Na) (TPPMS) or P(m-C6H4SO3Na)3 (TPPTS) for representative aryl bromides, chlorides, or triflates. The catalyst prepared in situ from Pd(OAc)2 (0.001mol%) and 10 (0.002mol%) achieved 96,000 TON in the reaction of p-tolylboronic acid with 4-bromoacetophenone in water.
- Nishimura, Masato,Ueda, Masato,Miyaura, Norio
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p. 5779 - 5787
(2007/10/03)
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- An improved protocol for the preparation of 3-pyridyl- and some arylboronic acids
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3-Pyridylboronic acid was prepared in high yield and bulk quantity from 3-bromopyridine via a protocol of lithium-halogen exchange and "in situ quench". This technique was further studied and evaluated on other aryl halides in the preparation of arylboronic acids.
- Li, Wenjie,Nelson, Dorian P.,Jensen, Mark S.,Hoerrner, R. Scott,Cai, Dongwei,Larsen, Robert D.,Reider, Paul J.
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p. 5394 - 5397
(2007/10/03)
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- Sulphonamide derivatives
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Glutamate receptor function in a mammal may be potentiated using an effective amount of a compound of formulaR1—L—NHSO2R2??Iin whichR1 represents an unsubstituted or substituted aromatic or heteroaromatic group;R2 represents (1-6C)alkyl, (3-6C)cycloalkyl, (1-6C)fluoroalkyl, (1-6C)chloroalkyl, (2-6C)alkenyl, (1-4C)alkoxy(1-4C)alkyl, phenyl which is unsubstituted or substituted by halogen, (1-4C)alkyl or (1-4C)alkoxy, or a group, of formula R3R4N in which R3 and R4 each independently represents (1-4C)alkyl or, together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl, morpholino, piperazinyl, hexahydroazepinyl or octahydroazocinyl group; andL represents a (2-4C)alkylene chain which is unsubstituted or substituted by one or two substituents selected independently from (1-6C)alkyl, aryl(1-6C)alkyl, (2-6C)alkenyl, aryl(2-6C)alkenyl and aryl, or by two substituents which, together with the carbon atom or carbon atoms to which they are attached form a (3-8C)carbocyclic ring;and pharmaceutically acceptable salts thereof.Also disclosed are compounds of formula I, processes for preparing them and pharmaceutical compositions containing them.
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- Angiotensin II antagonizers which are condensed pyridine derivatives
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The invention concerns pharmaceutically useful novel compounds of the formula I, in which R1, R2, R3, R4, R5, R6, R7, X and Z have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.
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