- Photocatalytic Oxidative [2+2] Cycloelimination Reactions with Flavinium Salts: Mechanistic Study and Influence of the Catalyst Structure
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Flavinium salts are frequently used in organocatalysis but their application in photoredox catalysis has not been systematically investigated to date. We synthesized a series of 5-ethyl-1,3-dimethylalloxazinium salts with different substituents in the positions 7 and 8 and investigated their application in light-dependent oxidative cycloelimination of cyclobutanes. Detailed mechanistic investigations with a coumarin dimer as a model substrate reveal that the reaction preferentially occurs via the triplet-born radical pair after electron transfer from the substrate to the triplet state of an alloxazinium salt. The very photostable 7,8-dimethoxy derivative is a superior catalyst with a sufficiently high oxidation power (E=2.26 V) allowing the conversion of various cyclobutanes (with Eox up to 2.05 V) in high yields. Even compounds such as all-trans dimethyl 3,4-bis(4-methoxyphenyl)cyclobutane-1,2-dicarboxylate can be converted, whose opening requires a high activation energy due to a missing pre-activation caused by bulky adjacent substituents in cis-position.
- Hartman, Tomá?,Reisnerová, Martina,Chudoba, Josef,Svobodová, Eva,Archipowa, Nataliya,Kutta, Roger Jan,Cibulka, Radek
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p. 373 - 386
(2021/02/01)
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- Iridium-catalyzed direct C-H amidation of anilines with sulfonyl azides: Easy access to 1,2-diaminobenzenes
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An Ir(iii)-catalyzed regioselective C-H amidation of anilines with sulfonyl azides is described. The developed protocol has good compatibility with diverse functional groups, efficiently providing the monoamidated products with good to excellent yields un
- Wang, Lianhui,Yang, Zi,Yang, Mengqi,Zhang, Rongyi,Kuai, Changsheng,Cui, Xiuling
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supporting information
p. 8302 - 8307
(2017/10/19)
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- Mild and selective hydrogenation of nitro compounds using palladium nanoparticles supported on amino-functionalized mesocellular foam
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We present the utilization of a heterogeneous catalyst comprised of Pd nanoparticles supported on aminopropyl-functionalized siliceous mesocellular foam (Pd0-AmP-MCF) for the selective hydrogenation of aromatic, aliphatic, and heterocyclic nitro compounds to the corresponding amines. In general, the catalytic protocol exclusively affords the desired amine products in excellent yields within short reaction times with the reactions performed at room temperature under ambient pressure of H2. Moreover, the reported Pd nanocatalyst displayed excellent structural integrity for this transformation as it could be recycled multiple times without any observable loss of activity or leaching of metal. In addition, the Pd nanocatalyst could be easily integrated into a continuous-flow device and used for the hydrogenation of 4-nitroanisole on a 2.5 g scale, where the product p-anisidine was obtained in 95% yield within 2 h with a Pd content of less than 1 ppm.
- Verho, Oscar,Gustafson, Karl P. J.,Nagendiran, Anuja,Tai, Cheuk-Wai,B?ckvall, Jan-E.
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p. 3153 - 3159
(2015/02/03)
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- Synthesis and biological evaluation of 5-substituted derivatives of benzimidazole
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A series of eight novel 5-substituted derivatives of benzimidazole was synthesized by condensation of the corresponding diamine with ethyl 4-[4- -(2-chlorophenyl)piperazin-1-yl]butanoate in refluxing 4 M hydrochloric acid. In vitro antibacterial activity against ten strains, namely Bacillus subtilis, Clostridium sporogenes, Streptosporangium longisporum, Micrococcus flavus, Sarcina lutea, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis and Proteus vulgaris and antifungal activity against two fungal strains, namely Candida albicans and Saccharomyces cerevisiae, were evaluated. Of all the compounds screened for activity, 2-{3-[4-(2-chlorophenyl) piperazin-1-yl]propyl}-5-iodo-1H-benzimidazole and 2-{3-[4-(2-chlorophenyl) piperazin-1-yl]propyl}-5-methyl-1H-benzimidazole were associated with higher antifungal activity than commercial drugs.
- Vasic, Vesna P.,Penjisevic, Jelena Z.,Novakovic, Irena T.,Sukalovic, Vladimir V.,Andric, Deana B.,Kostic-Rajacic, Sladana V.
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p. 277 - 282
(2014/04/17)
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- Synthesis of riboflavines, quinoxalinones and benzodiazepines through chemoselective flow based hydrogenations
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Robust chemical routes towards valuable bioactive entities such as riboflavines, quinoxalinones and benzodiazepines are described. These make use of modern flow hydrogenation protocols enabling the chemoselective reduction of nitro group containing building blocks in order to rapidly generate the desired amine intermediates in situ. In order to exploit the benefits of continuous processing the individual steps were transformed into a telescoped flow process delivering selected benzodiazepine products on scales of 50 mmol and 120 mmol respectively.
- Baumann, Marcus,Baxendale, Ian R.,Hornung, Christian H.,Ley, Steven V.,Rojo, Maria Victoria,Roper, Kimberley A.
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p. 9736 - 9759
(2014/08/05)
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- Naphthoylene(trifluoromethylbenzimidazole)-dicarboxylic acid imides for high-performance n-type organic field-effect transistors
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1,8-Naphthoylene(trifluoromethylbenzimidazole)-4,5-dicarboxylic acid imide (NTFBII) derivatives were synthesized. The OFET devices based on these new materials showed typical n-type OFET behavior and achieved an electron mobility as high as 0.10 cm2
- Deng, Ping,Yan, Yan,Wang, Sui-Dong,Zhang, Qing
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supporting information; experimental part
p. 2591 - 2593
(2012/04/17)
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- ENANTIOMERICALLY ENRICHED ARYLOAZOL-2-YL CYANOETHYLAMINO COMPOUNDS, METHOD OF MAKING AND METHOD OF USING THEREOF
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The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives substantially enriched in an enantiomer of formula (I): and compounds of formula (IH) wherein R3, R4, R5, R6, R7, R13a, R13b, R14a, R14b, P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.
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Page/Page column 43
(2010/06/13)
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- Synthesis, vasorelaxant activity and antihypertensive effect of benzo[d]imidazole derivatives
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A series of 1H-benzo[d]imidazole analogues of Pimobendan, substituted at position 5 with either -CF3 or -NO2, were synthesized using a short synthetic route. All the nitro derivatives were potent, and exhibited a concentration- and partial endothelium-dependent vasorelaxant effects, with EC50s 50 value of 1.81 μM and Emax of 91.7% for ex vivo relaxant response in intact aortic rings, resulting in a 2.5-fold higher activity compared to Pimobendan. The closely related 5-CF3 analogue (compound 8), was 19 times less potent than 13. The antihypertensive activity of compound 13 was evaluated at doses of 25, 50 and 100 mg kg-1, using spontaneously hypertensive rats (SHR), showing a statistically significant dose-dependent effect.
- Navarrete-Vázquez, Gabriel,Hidalgo-Figueroa, Sergio,Torres-Piedra, Mariana,Vergara-Galicia, Jorge,Rivera-Leyva, Julio Cesar,Estrada-Soto, Samuel,León-Rivera, Ismael,Aguilar-Guardarrama, Berenice,Rios-Gómez, Yolanda,Villalobos-Molina, Rafael,Ibarra-Barajas, Maximiliano
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experimental part
p. 3985 - 3991
(2010/08/06)
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- Heterocyclic Compounds Useful as RAF Kinase Inhibitors
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The present invention provides compounds useful as inhibitors of Raf protein kinase. The present invention also provides compositions thereof, and methods of treating Raf-mediated diseases.
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Page/Page column 43
(2009/01/24)
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- COMPOUNDS USEFUL AS RAF KINASE INHIBITORS
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The present invention provides compounds useful as inhibitors of Raf protein kinase. The present invention also provides compositions thereof, and methods of treating Raf-mediated diseases.
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Page/Page column 88
(2009/03/07)
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- ORGANIC COMPOUND, CHARGE-TRANSPORTING MATERIAL, COMPOSITION FOR CHARGE-TRANSPORTING MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE
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An organic compound having excellent heat resistance, an excellent amorphous nature, an excellent ability to transport charges, highly excited singlet and triplet states, and excellent solubility in an organic solvent is an organic compound represented by Formula (I): wherein Ar1 represents an optionally-substituted aromatic hydrocarbon group, an optionally-substituted aromatic heterocyclic group, or an optionally-substituted alkyl group; Ar2 represents an optionally-substituted aromatic hydrocarbon group or an optionally-substituted aromatic heterocyclic group; R1 and R2 each represent a hydrogen atom or a substituent, and R1 and R2 may be bonded to each other to form a ring; and Q is represented by Formula (I-1) or (I-2): wherein Ar3 to Ar5 each represent an optionally-substituted aromatic hydrocarbon group or an optionally-substituted aromatic heterocyclic group, and Ar3 and Ar4 may be bonded to each other to form a ring.
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Page/Page column 64
(2008/12/07)
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- ARYLOAZOL-2-YL CYANOETHYLAMINO COMPOUNDS, METHOD OF MAKING AND METHOD OF USING THEREOF
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The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives of formula (I):wherein R3, R4, R5, R6, R7, P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.
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Page/Page column 52
(2009/01/20)
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- Benzimidazole compound
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An object of the present invention is to provide a novel chemical compound useful as a therapeutic or prophylactic agent for acid-related diseases, having an excellent inhibitory effect against gastric acid secretion, an excellent effect of maintaining the inhibitory effect against gastric acid secretion, thereby maintaining intragastric pH high for a long time, and having more safety and appropriate physicochemical stability. Provided is a compound represented by where R1 and R3 may be the same or different and each represent a hydrogen atom or a C1-C6 alkyl group; R2 represents (5,5-dimethyl-1,3-dioxan-2-yl)methoxy group, 5,7-dioxaspiro[2.5]oct-6-ylmethoxy group, 1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy group, or (2,2-dimethyl-1,3-dioxan-5-yl)methoxy group; R4, R5, R6 and R7 represent a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group or C1-C6 haloalkoxy group; and W1 represents a single bond, methylene or ethylene group, a salt thereof or a solvate of these.
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Page/Page column 73
(2008/06/13)
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- Design and synthesis of novel 7-heterocycle-6-trifluoromethyl-3- oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group as superior AMPA receptor antagonists with good physicochemical properties
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We describe the design, synthesis, and physicochemical and biological properties of a novel series of 7-heterocycle-6-trifluoromethyl-3- oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group joined through a urethane or urea linkage to the heterocycle at the 7 position. Introduction of the trifluoromethyl group at the 6 position conferred good biological activity, including neuroprotective effects, as well as good physicochemical properties. In terms of α-amino-3-hydroxy-5- methylisoxazole propionate receptor (AMPA-R) affinity, a urea linkage was equivalent to a urethane linkage and a pyrrole ring at the 7 position reduced affinity in comparison with an imidazole ring. Among this series, compound 14h (KRP-199), which has a 4-carboxyphenyl group joined through a urethane linkage to a 7-imidazolyl heterocycle, was found to possess high potency and selectivity for the AMPA-R in vitro and to exhibit good neuroprotective effects in vivo. Furthermore, the compound showed good physicochemical properties, including stability to light and good solubility in aqueous solutions.
- Takano, Yasuo,Shiga, Futoshi,Asano, Jun,Hori, Wataru,Fukuchi, Kazunori,Anraku, Tsuyoshi,Uno, Takashi
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p. 776 - 792
(2007/10/03)
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- Synthesis and antiprotozoal activity of some 2-(trifluoromethyl)-1H- benzimidazole bioisosteres
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A series of 2-(trifluoromethyl)-1H-benzimidazole derivatives with various 5- and 6-position bioisosteric substituents (-Cl, -F, -CF3, -CN), namely 1-7, were prepared using a short synthetic route. Each analogue was tested in vitro against the protozoa Giardia intestinalis and Trichomonas vaginalis in comparison with albendazole and metronidazole. Several analogues had IC50 values 1 μM against both species, which make them significantly more potent than either standard. Compound 4 [2,5(6)- bis(trifluoromethyl)-1H-benzimidazole], was 14 times more active than albendazole against T.:vaginalis. This compound (4) also showed moderate antimalarial activity against W2 and D6 strains of Plasmodium falciparum (5.98 and 6.12 μM, respectively). Studying further structure activity relationships through the use of bioisosteric substitution in these benzimidazolic derivatives should provide new leads against protozoal and possibly malarial diseases.
- Navarrete-Vazquez, Gabriel,Rojano-Vilchis, Maria De Monserrat,Yepez-Mulia, Lilian,Melendez, Victor,Gerena, Lucia,Hernandez-Campos, Alicia,Castillo, Rafael,Hernandez-Luis, Francisco
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p. 135 - 141
(2007/10/03)
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- CHARGE-TRANSPORT MATERIALS, METHODS OF FABRICATION THEREOF, AND METHODS OF USE THEREOF
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Briefly described, embodiments of this disclosure include charge-transport materials, methods of forming charge-transport materials, and methods of using the charge-transport materials.
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Page/Page column 112
(2008/06/13)
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- Solvent-free reduction of aromatic nitro compounds with alumina-supported hydrazine under microwave irradiation
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Aromatic nitro compounds are readily reduced to the corresponding amino compounds in good yield with hydrazine hydrate supported on alumina in the presence of FeCl3·6H2O, Fe(III) oxide hydroxide or Fe(III) oxides.
- Vass, András,Dudás, József,Tóth, Judit,Varma, Rajender S.
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p. 5347 - 5349
(2007/10/03)
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- Synthesis of substituted 2-ethoxycarbonyl- and 2-carboxyquinoxalin -3 ones for evaluation of antimicrobial and anticancer activity
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A series of variously substituted quinoxalin-3-ones bearing an ethoxycarbonyl or carboxy group in the C-2 position has been prepared and their structures proved by 1H NMR spectroscopy. The obtained compounds were investigated in vitro for antimicrobial and anticancer activities. Preliminary results showed a moderate activity against a few strains of bacteria but no significant anticancer and anti-HIV activity.
- Sanna, Paolo,Carta, Antonio,Loriga, Mario,Zanetti, Stefania,Sechi, Leonardo
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p. 455 - 461
(2007/10/03)
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- Glycine receptor antagonists and the use thereof
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Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, inducing anesthesia and treating psychosis are disclosed by administering to an animal in need of such treatment a compound having high affinity for the glycine binding site, lacking PCP side effects and which crosses the blood brain barrier of the animal. Also disclosed are novel 1,4-dihydroquinoxaline-2,3-diones, and pharmaceutical compositions thereof. Also disclosed are highly soluble ammonium salts of 1,4-dihydroquinoxaline-2,3-diones.
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- Synthesis and structure-activity relationships of substituted 1,4- dihydroquinoxaline-2,3-diones: Antagonists of N-methyl-D-aspartate (NMDA) receptor glycine sites and non-NMDA glutamate receptors
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A series of mono-, di-, tri-, and tetrasubstituted 1,4- dihydroquinoxaline-2,3-diones (QXs) were synthesized and evaluated as antagonists at N-methyl-D-aspartate (NMDA)/glycine sites and α-amino-3- hydroxy-5-methylisoxazole-4-propionic acid-preferring non-NMDA receptors. Antagonist potencies were measured by electrical assays in Xenopus oocytes expressing rat whole brain poly(A)+ RNA. Trisubstituted QXs 17a (ACEA 1021), 17b (ACEA 1031), 24a, and 27, containing a nitro group in the 5 position and halogen in the 6 and 7 positions, displayed high potency (K(b) ~ 6-8 nM) at the glycine site, moderate potency at non-NMDA receptors (K(b) = 0.9-1.5 μM), and the highest (120-250-fold) selectivity in favor of glycine site antagonism over non-NMDA receptors. Tetrasubstituted QXs 17d,e were more than 100-fold weaker glycine site antagonists than the corresponding trisubstituted QXs with F being better tolerated than Cl as a substituent at the 8 position. Di- and monosubstituted QXs showed progressively weaker antagonism compared to trisubstituted analogues. For example, removal of the 5-nitro group of 17a results in a ~100-fold decrease in potency (10a,b,z), while removal of both halogens from 17a results in a ~3000-fold decrease in potency (10v). In terms of steady-state inhibition, most QX substitution patterns favor antagonism at NMDA/glycine sites over antagonism at non-NMDA receptors. Among the QXs tested, only 17i was slightly selective for non- NMDA receptors.
- Keana,Kher,Sui Xiong Cai,Dinsmore,Glenn,Guastella,Huang,Ilyin,Lu,Mouser,Woodward,Weber
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p. 4367 - 4379
(2007/10/02)
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- 2-(4-pyridylaminomethyl)-benzimidazole derivatives having antiviral activity
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Provided herein is an antiviral 2-(4-pyridylaminomethyl)-benzimidazole of the formula: STR1 wherein R is a radical selected from the groups consisting of hydrogen, short-chain alkyl, short-chain alkoxy, benzoyl, halogenomethyl, halogen, nitro and amino groups; the preparation of these compounds and antiviral composition containing such compounds.
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- Substituted 1-sulfonylbenzimidazoles
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Certain 1-sulfonyl-2,5(6)-substituted-benzimidazole compounds are useful as antiviral agents.
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- Quinoxaline compounds as hypnotic agents
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The present invention is concerned with the use of certain quinoxaline compounds as hypnotic agents.
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