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  • Synthesis of 4-(2H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one via Ring-Switching Hydrazinolysis of 5-Ethoxymethylidenethiazolo [3,2-b][1,2,4]triazol-6-one

Synthesis of Multifunctional Spirocyclic Azetidines and Their Application in Drug Discovery

Chem. Eur. J. 2018, 24 (21), 5444-5449

DOI: 10.1002/chem.201800193

Kirichok A.; Shton I.; Pishel I.; Zozulya S.; Borysko P.; Kubyshkin V.; Zaporozhets O.; Tolmachev A.; Mykhailiuk P.

The synthesis of multifunctional spirocycles was achieved from common cyclic carboxylic acids (cyclobutane carboxylate, cyclopentane carboxylate, l-proline, etc.). The whole sequence included only two chemical steps—synthesis of azetidinones, and reduction into azetidines. The obtained spirocyclic amino acids were incorporated into a structure of the known anesthetic drug Bupivacaine. The obtained analogues were more active and less toxic than the original drug. We believe that this discovery will lead to a wide use of spirocyclic building blocks in drug discovery in the near future.

Synthesis of Multifunctional Spirocyclic Azetidines and Their Application in Drug Discovery

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