Synthesis of dihydropyridine and piperidine derivatives via an unexpected reaction of pyridine with acetyl chloride

Acetyl chloride reacts with pyridine to give a mixture of N-acetyl-1,4- and 1,2-dihydropyridyl acetic acid (1a,b) after water quenching. The reactioninvolves the formation of a zwitterionic ketene enolate intermediate which results from deprotonation of the acetyl moiety of the in situ formed N-acetyl pyridinium ion. The effect on the reaction outcome of different parameters as temperature, pyridine/acetyl chloride molar ratio, and as Lewis acids and triflate counterion presence has been studied in detail, and a reaction mechanism has been proposed

Sintesi stereoselettiva di ureido-zuccheri via 5-(alditol-1-C-il) idantoina building blocks: effetto del gruppo protettivo dell'idantoina sulla diastereoselettività

In questo lavoro verrà presentata la sintesi stereoselettiva di interessanti ureido-zuccheri che sfrutta 5-poliidrossialchil-idantoine come building blocks. Presenteremo inoltre uno studio sull’effetto del gruppo protettivo dell’idantoina sulla disatereoselettività della reazione con aldeidi omochirali

Expeditious synthesis of the key unnatural aminoacid in the formal asymmetric total synthesis of (-)-Jorumycin and bioactive tetrahydroisoquinoline alkaloids

The synthesis of the enantiopure aminoacid, key intermediate in the total synthesis of (-)-Jorumycin and of various bioactive tetraidroisoquinoline alkaloids analogues, a class of compounds with antitumor and antibiotic activities, has been accomplished starting from 2,4-dimethoxy-3-methyl-benzaldehyde 1 in only 5 steps and in a very high yield. This synthesis, based on a Negishi reaction between a 5-iodo-2,4-dimethoxy-3-methylphenol and N-(tert-Butoxycarbonyl)-3-iodo-L-alanine methyl ester, permits an easy access to the intermediate, and the formal asymmetric total synthesis of (-)-Jorumycin and tetrahydroisoquinoline alkaloids of the same family, in a very shorter way with respect to the syntheses previously reported

Novel caspase inhibitors

The present invention provides novel compounds of formula (I) that are potent and selective non-covalent caspase inhibitors. These compounds nay be used for the treatment of inflammatory diseases

Sintesi totale di analoghi dell'Isofagomina

In questo lavoro viene presentata una nuova strategia, stereoselettiva e flessibile per la sintesi di D-galacto- e L-allo-isofagomina utilizzando come precursori 5-triidrossipropil-diidrouracil derivati ottenuti dalla semplice addizione diastereoselettiva di tipo aldolica di immidi enolati dell’1,3-dibenzildiidrouracile a 2,3-O-isopropilidene-D-gliceraldeide

Design, synthesis and biological evaluation of 1,5-disubstituted α-amino tetrazole derivatives as non-covalent inflammasome-caspase-1 complex inhibitors with potential application against immune and inflammatory disorders

Compounds targeting the inflammasome-caspase-1 pathway could be of use for the treatment of inflammation and inflammatory diseases. Previous caspase-1 inhibitors were in great majority covalent inhibitors and failed in clinical trials. Using a mixed modelling, computational screening, synthesis and in vitro testing approach, we identified a novel class of non-covalent caspase-1 non cytotoxic inhibitors which are able to inhibit IL-1β release in activated macrophages in the low μM range, in line with the best activities observed for the known covalent inhibitors. Our compounds could form the basis of further optimization towards potent drugs for the treatment of inflammation and inflammatory disorders including also dysregulated inflammation in Covid 19

Enantioselective synthesis of (<i>S</i>)- and (<i>R</i>)-tolterodine by asymmetric hydrogenation of a coumarin derivative obtained by a Heck reaction

An efficient and short enantioselective synthesis of (S)- and (R)-tolterodine was performed by asymmetric hydrogenation of a coumarin intermediate, easily obtained by a Heck reaction from inexpensive and commercially available starting materials