65699-84-5Relevant academic research and scientific papers
Structure-property relationships and nonlinear optical effects in donor-substituted dicyanopyrazine-derived push-pull chromophores with enlarged and varied π-linkers
Bures, Filip,Cermakova, Hana,Kulhanek, Jiri,Ludwig, Miroslav,Kuznik, Wojciech,Kityk, Iwan V.,Mikysek, Tomas,Ruzicka, Ales
supporting information; experimental part, p. 529 - 538 (2012/03/09)
Thirteen new, stable, push-pull systems featuring dimethylamino and pyrazine-2,3-dicarbonitrile moieties as the donor and acceptor, respectively, and systematically extended and varied π-linkers were prepared and investigated. Evaluation of the measured UV/Vis spectra, electrochemical data (cyclic voltammetry, rotating disc voltammetry, and polarography), X-ray data, and experimentally determined and calculated hyperpolarizability values enabled structure-property studies; these revealed some important structural features that affected the efficiency of intramolecular charge-transfer and nonlinear optical properties in this class ofheterocyclic push-pull chromophores. The charge-transfer transition was most significantly affected by structuralfeatures such as π-linker length, chromophore planarity, and the number of 1,4-phenylene/ethynylene subunits in the π-linker. Linear and nonlinear optical properties of push-pull chromophores featuring a pyrazine-2,3- dicarbonitrile acceptor moiety and dimethylamino donors were modulated by systematic extension and variation of the π-linker. The length and character of the π-linker used significantly influenced the efficiency of the donor-acceptor conjugation and nonlinear responses. Copyright
Substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one as CB 1 cannabinoid receptor ligands: Synthesis and pharmacological evaluation
Muccioli, Giulio G.,Martin, Diana,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Poupaert, Jacques H.,Wouters, Johan,Lambert, Didier M.
, p. 2509 - 2517 (2007/10/03)
A set of 30 substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one (thiohydantoins) derivatives was synthesized, and their affinity for the human CB1 cannabinoid receptor has been evaluated. These compounds are derived from the previously described cannabinoid ligands 5,5′- diphenylimidazolidine-2,4-dione (hydantoins). The replacement of the oxygen by a sulfur leads to an increase of the affinity while the function-i.e., inverse agonism-determined by [35S]-GTPγS experiments remains unaffected. Finally, to evaluate the molecular parameters that could influence the affinity of the thiohydantoins, molecular electrostatic potential as well as lipophilicity calculations were undertaken on representative thiohydantoins and hydantoins derivatives. In conclusion, 5,5′-bis-(4-iodophenyl)-3-butyl-2- thioxoimidazolidin-4-one (31) and 3-allyl-5,5′-bis(4-bromophenyl)-2- thioxoimidazolidin-4-one (32) possess the highest affinity for the CB 1 cannabinoid receptor described to date for the hydantoin and thiohydantoins series when compared in a same bioassay.
1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: New templates among the CB1 cannabinoid receptor inverse agonists
Muccioli, Giulio G.,Wouters, Johan,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Poupaert, Jacques H.,Lambert, Didier M.
, p. 7486 - 7490 (2007/10/03)
New 1-benzhydryl-3-phenylurea derivatives and their 1-benzhydryl-3- phenylthiourea isosteres were synthesized and evaluated for their human CB 1 and CB2 cannabinoid receptor affinity. These compounds proved to be selective CB1 cannabinoid receptor ligands, acting as inverse agonists in a [35S]-GTPγS assay. The affinity of 3,5,5′-triphenylimidazolidine-2,4-dione and 3,5,5′-triphenyl-2- thioxoimidazolidin-4-one derivatives, possessing the 1-benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea moiety, respectively, was also evaluated. In conclusion, the 1-benzhydryl-3-phenylurea scaffold seems to be a new interesting template of CB1 cannabinoid receptor inverse agonists.
TRANSITION-METAL CHARGE-TRANSPORT MATERIALS, METHODS OF FABRICATION THEREOF, AND METHODS OF USE THEREOF
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Page/Page column 81, (2010/02/15)
Briefly described, embodiments of this disclosure include transition-metal charge-transport materials, methods of forming transition-metal charge-transport materials, and methods of using the transition-metal charge-transport materials.
Samarium diiodide promoted formation of 1,2-diketones and 1-acylamido-2-substituted benzimidazoles from N-acylbenzotriazoles
Wang, Xiaoxia,Zhang, Yongmin
, p. 4201 - 4207 (2007/10/03)
N-Acylbenzotriazoles, when treated with samarium diiodide in THF, undergo self-coupling reaction to afford 1,2-diketones in good to excellent yields; while when treated with samarium diiodide in CH3CN, they undergo ring-opening reaction to afford 1-acylamido-2-alkyl (or aryl) benzimidazoles in reasonable to good yields. A plausible mechanism was suggested.
A new ytterbium iodide mediated coupling of acyl cyanides and synthesis of 1,2-diketones
Saikia, Promod,Laskar, Dhrubojyoti D.,Prajapati, Dipak,Sandhu, Jagir S.
, p. 7525 - 7526 (2007/10/03)
Conversion of acyl cyanides 1 into 1,2-diketones 2 has been achieved by the action of ytterbium iodide in dry tetrahydrofuran at room temperature, in high yields.
Formation of 1,2-diketones by samarium diiodide promoted reaction of N-acylbenzotriazoles
Wang, Xiaoxia,Zhang, Yongmin
, p. 5431 - 5433 (2007/10/03)
Transformation of N-acylbenzotriazoles 1 into 1,2-diketones 2 in good to excellent yields has been realized by the use of samarium diiodide at room temperature.
Sm or Zn-induced coupling reactions. A facile route to 1,2-diketones
Baruah, Bipul,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S
, p. 7603 - 7604 (2007/10/03)
Coupling of keto cyanides 1 into 1,2-diketones 2 has been performed by the action of SmI2 or ZnI2 in tetrahydrofuran at ambient temperature in high yields.
Synthesis of new aryl and hetaryl dibromides and diiodides, the monomers for preparation of polyarylene ethynylenes
Rusanov,Keshtov,Begretov,Khotina,Mikitaev
, p. 1169 - 1175 (2007/10/03)
Dibromides and diiodides with quinoxaline, phenylimidazole, and hexa-or pentaphenylarylene fragments were synthesized from dihalotolans obtained from chloral. Oligoarylene ethynylenes were synthesized by the reaction of the monomers with equimolar amounts of diethynyl aromatic compounds in the presence of the Pd11 complex. Oligomers with imidazole and hexa(penta)arylbenzene cycles are soluble in amide organic solvents and their reduced viscosities do not exceed 0.09 dL g-1.
DI(ACYLOXY)IODOARENES IN ORGANIC SYNTHESIS. III. REACTION OF DIARYLACETYLENES WITH BIS(TRIFLUOROACETOXY)IODOBENZENE
Vasil'eva, V. P.,Khalfina, I. L.,Karpitskaya, L. G.,Merkushev, E. B.
, p. 1967 - 1969 (2007/10/02)
Bis(trifluoroacetoxy)iodobenzene in chloroform oxidizes diarylacetylenes containing electron-donating and not very strong electron-withdrawing substituents to the corresponding benzils with high yields.The reaction probably takes place through the intermediate formation of vinyl- and alkyliodonium salts.Benzoin is oxidized to benzil.
