170124-07-9Relevant academic research and scientific papers
Ortho-Quinol Acetate Chemistry: Reactivity toward Aryl-Based Nucleophiles and Applications to the Synthesis of Natural Products
Companys, Simon,Pouységu, Laurent,Peixoto, Philippe A.,Chassaing, Stefan,Quideau, Stéphane
, p. 3990 - 3995 (2017/04/11)
Two model ortho-quinol acetates were easily prepared by iodane-mediated acetoxylative phenol dearomatization and evaluated for their reactivity toward various aryl-based nucleophiles, i.e., aryl metallic reagents and phenolic derivatives. Novel modes of reactivity, allowing the formation of biaryl linkages, were revealed and here exploited for the synthesis of two natural phenolics.
Novel class of benzoic acid ester derivatives as potent PDE4 inhibitors for inhaled administration in the treatment of respiratory diseases
Armani, Elisabetta,Amari, Gabriele,Rizzi, Andrea,Fanti, Renato De,Ghidini, Eleonora,Capaldi, Carmelida,Carzaniga, Laura,Caruso, Paola,Guala, Matilde,Peretto, Ilaria,La Porta, Elena,Bolzoni, Pier T.,Facchinetti, Fabrizio,Carnini, Chiara,Moretto, Nadia,Patacchini, Riccardo,Bassani, Franco,Cenacchi, Valentina,Volta, Roberta,Amadei, Francesco,Capacchi, Silvia,Delcanale, Maurizio,Puccini, Paola,Catinella, Silvia,Civelli, Maurizio,Villetti, Gino
supporting information, p. 793 - 816 (2014/03/21)
The first steps in the selection process of a new anti-inflammatory drug for the inhaled treatment of asthma and chronic obstructive pulmonary disease are herein described. A series of novel ester derivatives of 1-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3,5-dichloropyridin-4- yl) ethanol have been synthesized and evaluated for inhibitory activity toward cAMP-specific phosphodiesterase-4 (PDE4). In particular, esters of variously substituted benzoic acids were extensively explored, and structural modification of the alcoholic and benzoic moieties were performed to maximize the inhibitory potency. Several compounds with high activity in cell-free and cell-based assays were obtained. Through the evaluation of opportune in vitro ADME properties, a potential candidate suitable for inhaled administration in respiratory diseases was identified and tested in an in vivo model of pulmonary inflammation, proving its efficacy.
Thiourea and benzamide compounds, compositions and methods of treating or preventing inflammatory diseases and atherosclerosis
-
, (2008/06/13)
The present invention provides compounds of formula (I). The present invention also provides methods of treating or preventing inflammation or atherosclerosis, and a pharmaceutical composition that contains a compound of formula (I).
Synthesis of Functionalized Aryloxy 1,3-Butadienes and Their Transformation to Diaryl Ethers via Diels-Alder Cycloaddition Reactions
Olsen, Richard K.,Feng, Xianqi,Campbell, Magnus,Shao, Rui-lian,Math, Shivanand K.
, p. 6025 - 6031 (2007/10/03)
The Diels-Alder reaction involving cycloaddition of aryloxy-substituted 1,3-butadienes with appropriate acetylenic electrophiles, followed by aromatization of the newly formed cyclohexadiene ring, has been used for the synthesis of diaryl ethers.The functionalized aryloxy 1,3-butadienes employed in this study were prepared by either of two methods: (1) methylenation of aryl esters via the Tebbe or related reagents, and (2) from 1-(aryloxy)-2-propanone by a sequence of formylation or alkylthio methylenation, and subsequent enolsilylation.A tetrasubstituted butadiene containing two phenoxy groups at the 1 and 3 positions also was prepared by the latter method.The cycloaddition reactions of 2,3-dioxy-substituted dienes occurred in high yield, but, as expected, with no regioselectivity to furnish nearly equal mixtures of regioisomeric cycloadducts.In contrast, application of 1,2,3-trihetero-substituted dienes resulted in regiospecific cycloaddition reactions.Transformation of the cyclohexadiene cycloadducts to an aromatic ring was accomplished by dehydrogenation with DDQ or by elimination during the cycloaddition process of a molecule of an alkyl mercaptan.A chiral acetylenic ketone derived from D- or L-serine underwent condensation, without racemization, with aryloxy dienes to provide diaryl ethers related to the isodityrosine antibiotics.
