- Benzo[d]thiazol-2(3H)-ones as new potent selective CB2 agonists with anti-inflammatory properties
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The high distribution of CB2 receptors in immune cells suggests their important role in the control of inflammation. Growing evidence offers this receptor as an attractive therapeutic target: selective CB2 agonists are able to modula
- Leleu-Chavain, Natascha,Baudelet, Davy,Heloire, Valéria Moas,Rocha, Diana Escalante,Renault, Nicolas,Barczyk, Amélie,Djouina, Madjid,Body-Malapel, Mathilde,Carato, Pascal,Millet, Régis
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- Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression
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A series of benzothiazol-2-one containing α-ethoxyphenylpropionic acid derivatives incorporating resveratrol or butein scaffolds were designed as fused full PPARγ agonist ligands and SIRT1-activating compounds for the treatment of type 2 diabetes (T2D) an
- Pirat, Celine,Dacquet, Catherine,Leclerc, Veronique,Hennuyer, Nathalie,Beucher-Gaudin, Monique,Zanirato, Ghislaine,Géant, Anne,Staels, Bart,Ktorza, Alain,Farce, Amaury,Caignard, Daniel-Henri,Berthelot, Pascal,Lebegue, Nicolas
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Read Online
- CuI-catalyzed one-pot synthesis of benzothiazolones from 2-iodoanilines-derived carbamates and sodium sulfide
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A copper-catalyzed procedure was developed for assembling benzothiazolones from ethyl 2-iodophenylcarbamates and sodium sulfide. A number of functional groups, such as methoxy, acyl, amide, carboxylate, trifluoromethyl, fluoro, and chloro, were tolerated under these conditions, providing benzothiazolones in good yields.
- Li, Jiaojiao,Zhang, Yihua,Jiang, Yongwen,Ma, Dawei
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supporting information; experimental part
p. 2511 - 2513
(2012/06/16)
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- Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)- benzothiazolone derivatives
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A simpler and efficient "green" method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. Graphical abstract: [Figure not available: see fulltext.]
- Guenadil, Faouzi,Aichaoui, Hocine,Kapanda, Coco N.,Lambert, Didier M.,McCurdy, Christopher R.,Poupaert, Jacques H.
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experimental part
p. 67 - 80
(2011/09/20)
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- Application of the "fries like" rearrangement using ZnCL 2 for the synthesis of 6-acyl-2(3H)-benzothiazolones
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In this work we report another method of acylation on the 6-position of the 2(3H)-benzothiazolone ring with Fries-like rearrangement catalyzed by zinc chloride instead of aluminium chloride and 3-acyl-2(3H)-benzothiazolones derivatives as starting materia
- Guenadil, Faouzi,Aichaoui, Hocine
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p. 1703 - 1708
(2007/10/03)
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- Study of the acylation reaction of 2(3H)-benzothiazolones in the mixture of ZnCl2-DMF
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The use of polyphosphoric acid and the complex AlCl3-DMF in 6-acylation of 2(3H)-benzothiazolones previously have been reported. Instead of the frequently used AlCl3 as a catalyst in the Friedl-Crafts reactions, we conducted the acyl
- Guenadil, Faouzi,Aichaoui, Houcine
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p. 2633 - 2638
(2007/10/03)
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- 'Fries like' rearrangement: A novel and efficient method for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones
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6-Acyl-2(3H)-benzoxazolone and 6-acyl-2(3H)-benzothiazolone derivatives have particularly interesting anti-inflammatory, antiepileptic, analgesic and antiviral properties. In this study, we report an original method of acylation on the 6-position of 2(3H)-banzoxazolone and 2(3H)benzothiazolone which consists in a two-step procedure involving migration of the acyl group from the N-position to the 6-position of the hetexocycle, at 165 °C and catalyzed by AlCl3. This new procedure was found to be more efficient with regard to the consumption of AICI3 and the yield (76-90%) than other acylation methods previously described.
- Ucar, Huseyin,Van Derpoorten, Kim,Depovere, Paul,Lesieur, Daniel,Isa, Majed,Masereel, Bernard,Delarge, Jacques,Poupaert, Jacques H.
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p. 1763 - 1772
(2007/10/03)
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- Benzothiazolinone compounds
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Compounds of general formula (I): STR1 in which: R1 represents a hydrogen atom or a lower alkyl group, R2 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstitute
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