Synthesis of tri- and tetramines containing two 2,3-dihydroxypyrrolidine moieties and their inhibitory activity toward α-mannosidases

Through the reductive amination of N-[(tert-butoxy)carbonyl]-2,5-dideoxy-2,5-imino-3,4-Oisopropylidene-L-ribose with tetramethylenediamine, hexamethylenediamine, 2,7- diaminofluorene, 4,4'-diaminodiphenylmethane and 1,4-(diaminomethyl)benzene, five tetramines containing two (2R,3R,4S)-2-aminomethylpyrrolidine-3,4-diol moieties have been prepared and assayed for their inhibitory activities toward 24 glycosidases. Tetramines containing the tetramethylene or benzene-1,4-dimethylene linkers are more potent αmannosidase inhibitors than simple (2R,3R,4S)-2-aminomethylpyrrolidine-3,4-diols. Triamines such as (2S,3R,4S)-bis(3,4-dihydroxy-pyrrolidin-2-ethyl)amine were also prepared and shown to be better α-mannosidase inhibitors than (2S,3R,4S)-2-(2-aminoethyl)pyrrolidin-3,4-diol.The Swiss National Science Foundation (grants n° 20-63667.00 and 2100-063567.00/1)European COST (COST D13/0001/99) programOffice Fédéral de l'Education et de la Science (Bern)Dirección General de Investigación Científica y Técnica of Spain (grant n° BQU-2001-3779)SOCRATES (EPFL/Sevilla) progra

Synthesis of tri- and tetramines containing two 2,3-dihydroxypyrrolidine moieties and their inhibitory activity toward α-mannosidases

Through the reductive amination of N-[(tert-butoxy)carbonyl]-2,5-dideoxy-2, 5-imino-3,4-O-isopropylidene-L-ribose with tetramethylenediamine, hexamethylenediamine, 2,7-diaminofluorene, 4,4′-diaminodiphenylmethane and 1,4-(diaminomethyl)benzene, five tetramines containing two (2R,3R,4S)-2- aminomethylpyrrolidine-3,4-diol moieties have been prepared and assayed for their inhibitory activities toward 24 glycosidases. Tetramines containing the tetramethylene or benzene-1,4-dimethylene linkers are more potent α-mannosidase inhibitors than simple (2R,3R,4S)-2-aminomethylpyrrolidine- 3,4-diols. Triamines such as (2S,3R,4S)-bis(3,4-dihydroxy-pyrrolidin-2-ethyl) amine were also prepared and shown to be better α-mannosidase inhibitors than (2S,3R,4S)-2-(2-aminoethyl)pyrrolidin-3,4-diol

Nitrogen-functionalized Isohexides in Asymmetric Induction

Biosourced isohexides have attracted the considerable attention of both the academic and industrial chemistry communities over the last 50 years. This highlight focuses on the synthesis of nitrogen-containing isohexides and their applications in asymmetric catalysis

Regioselective Late-Stage C-3 Functionalization of Pyrazolo[3,4-b]pyridines

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Straightfoward synthesis of 2-acetyl-substituted benzo[b]thiophenes

International audienceDescribed herein is a green one-step protocol for the preparation of substituted 2-acetylbenzo[b]thiophenes from commercially available aromatic halides. This efficient method has the advantage of using water as the reaction medium, resulting in a high yield of pure cyclized products. Two scaffold types have been prepared using this general procedure: 2-acetylbenzo[b]thiophenes and 2-acetyl-3-aminobenzo[b]thiophenes, both crystallized directly from the reaction mixture, due to their low solubility with water, and without the need for an additional purification step. ChemInform Abstract: Straightforward Synthesis of 2-Acetyl-Substituted Benzo[b]thiophenes. - ResearchGate. Available from: http://www.researchgate.net/publication/264576761_ChemInform_Abstract_Straightforward_Synthesis_of_2-Acetyl-Substituted_Benzobthiophenes [accessed Apr 28, 2015]

The synthesis of HMF-based α-amino phosphonates via one-pot Kabachnik–Fields reaction

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Direct arylation : alternative to classic cross-coupling chemistry and a fruitful synthetic tool for the access to novative bioactive molecules.

International audienceThis account will discuss the advances performed in our group on direct arylation of heterocyclic systems regarded as critical scaffolds of pharmaceutical industries due to their wide-ranging biological and therapeutical properties. Applications to larger molecules devoted to pharmaceutical, material or agrochemical industries should bring significant improvement, getting rid of the preliminary step of prefunctionalization

Nitrogen-functionalized Isohexides in Asymmetric Induction

Biosourced isohexides have attracted the considerable attention of both the academic and industrial chemistry communities over the last 50 years. This highlight focuses on the synthesis of nitrogen-containing isohexides and their applications in asymmetric catalysis

Reduction of aromatic and aliphatic nitro groups to anilines and amines with hypophosphites associated with Pd/C

International audienceThe reduction of aromatic and aliphatic nitro groups to anilines and amines is performed with good yield and selectivity in short reaction times. A mixture of sodium hypophosphite and phosphinic acid is used in the presence of a heterogeneous catalyst 2.5 mol% of Pd/C (5%) in a biphasic water/2-MeTHF system