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Control of the site and potential of reduction and oxidation processes in pi-expanded quinoxalinoporphyrins

Quinoxalino[2,3-b?]porphyrins are pi-expanded porphyrins, having a quinoxaline fused to a beta,beta?-pyrrolic position of the porphyrin. They are used as components in systems proposed as ‘molecular wires’. Knowledge of their redox properties is of value in the design of electron- or hole-conduction systems. In particular, the location of the charge density in the radical anions of quinoxalinoporphyrins can be modulated by peripheral functionalization. New theoretical treatments of electrochemical potentials are developed that identify the site of reduction in both the anions and the dianions of 33 quinoxalinoporphyrins. These molecules include free-base and metallated macrocycles substituted on the quinoxaline with electron-withdrawing groups (NO2, Cl, Br) and/or electron-donating groups (NH2, OCH3). Spectroelectrochemistry, density-functional theory calculations, and substituent-parameter models are used to verify the analysis. Five distinct patterns are observed for the locations of the first and second reductions; some of these patterns involve delocalized charges. Nitroquinoxalinoporphyrins with the nitro groups at the 5- and 6-quinoxaline positions are found to have quite different properties owing to distortions caused by peri interactions that force the nitro group of the 5-nitro regioisomer out of conjugation. Charge localization on the nitroquinoxaline fragment is found for some molecules, and this is attributed to ion-pairing with the 0.1 M tetrabutylammonium perchlorate electrolyte used, leading to the verified prediction that electron-paramagnetic resonance spectra of these molecules taken without the electrolyte yield delocalized anions. These properties enable the control of conduction through molecular wires synthesised from quinoxalinoporphyrins. the Owner Societies.

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VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS

Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritis, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

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HETEROCYCLIC DERIVATIVES THAT ARE USED IN THE TREATMENT OF NEURODEGENERATIVE DISEASES

The present invention relates to compounds of Formula (I) below, to their pharmaceutically acceptable salts and to their isomers or mixtures of isomers: HetAr?X?CHR1R2 (I) in which: -HetAr represents a group chosen from: ?X represents a linear, saturated or unsaturated, hydrocarbon-based chain comprising from 8 to 22 carbon atoms, optionally interrupted by an ?NH? or ?NH?CO? group, ?R1 represents a hydrogen atom or an ?OH, ?O(C1-C6)alkyl, ?OCO((C1-C6)alkyl), ?OSO2((C1-C6)alkyl) or ?OSO3H group, and ?R2 represents a hydrogen atom or a (C2-C6)alkynyl, (C2-C6)alkenyl or (C3-C6)cycloalkyl group. The present invention also relates to a process for preparing the compounds of Formula (I), and also to the use thereof, especially in the treatment of neurodegenerative diseases.

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ANTIVIRAL COMPOUNDS

The present invention relates to a compound of formula: (I) or a pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification; a pharmaceutical composition comprising the same, a method for treating or preventing a viral infection such as HIV using the same.

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5-AMINO-6-NITROQUINOXALINES FROM 6-NITROQUINOXALINES BY THE AMINATION REACTION WITH HYDROXYLAMINE.

The yields of the direct amination of 6-nitroquinoxalines by hydroxylamine have been improved, opening thus a better access to 1,4,5,8-tetra-azphenanthrenes.

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Palladium-catalyzed dearomative trimethylenemethane cycloaddition reactions

A general protocol for the palladium-catalyzed dearomative trimethylenemethane [3+2] cycloaddition reaction with simple nitroarene substrates is described. This methodology leads to the exclusive formation of the dearomatized alicyclic products without subsequent rearomatization. The reaction is tolerant toward a broad range of heterocyclic and benzenoid substrates. The use of chiral bisdiamidophosphite ligands enabled the development of an enantioselective variant of this transformation, representing one of the rare examples of an asymmetric catalytic dearomatization process.

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Quaternarized pdppz: Synthesis, DNA-binding and biological studies of a novel dppz derivative that causes cellular death upon light irradiation

The quaternarized pdppz derivative 1 was shown to bind strongly to DNA with concomitant changes in its ground and excited state photophysical properties. Furthermore, the compound also showed rapid cellular uptake, and induced apoptosis upon light irradiation in various cancer cell lines after 24 hours of incubation. The Royal Society of Chemistry 2011.

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Nucleophilic vinylic substitution (SNV) of activated alkoxymethylene derivatives with 6-aminoquinoxaline

Treatment of 6-aminoquinoxaline with beta,beta-diactivated alkoxymethylene derivatives gave the corresponding N-(quinoxalin-6-yl)enamines. A variant of the SNV reaction mechanism was proposed for substitution of the alkoxymethylene compounds, on the basis of the structures of the precursor enol ether and the vinylic substitution product and on computations. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

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Regioselectivity of the Amination of Some Nitroquinoxalines by Liquid Ammonia/Potassium Permanganate

5- and 6-Nitroquinoxalines and some of their derivatives are aminated in a liquid ammonia solution of potassium permanganate to yield the corresponding 2- and/or 3- and/or 5-amino compounds.Quantum-chemical calculations are made to explain the regioselectivity of the amination reactions. Key Words: Amination / Nitroquinoxalines / Reactivity indices / Calculations, MNDO / Quinoxalines

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Nano-TiO2: An eco-friendly alternative for the synthesis of quinoxalines

Nano-TiO2 as an eco-friendly and efficient nanocatalyst was applied for quinoxaline preparation with improved yield. In this protocol, diketones and 1,2-diamines were condensed in the presence of catalyst at room temperature.

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