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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Green One-Pot Asymmetric Synthesis of Peptidomimetics via Sequential Organocatalyzed Aziridination and Passerini Multicomponent Reaction

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dos Santos, Deborah A. [1, 2] ; da Silva, Allan R. [1, 2] ; Ellena, Javier [3] ; da Silva, Cecilia C. P. [1] ; Paixao, Marcio W. [1, 2] ; Correa, Arlene G. [1, 2]
Total Authors: 6
[1] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, BR-13565905 Sao Carlos, SP - Brazil
[3] Univ Sao Paulo, Sao Carlos Inst Phys, BR-13560570 Sao Carlos, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: SYNTHESIS-STUTTGART; v. 52, n. 7, p. 1076-1086, APR 1 2020.
Web of Science Citations: 0

Peptidomimetics containing an aziridine moiety have been reported as potent cysteine protease inhibitors. In this sense, the development of stereoselective and sustainable synthetic strategies to obtain three-membered N -heterocyclic compounds has gained importance in the last decades. In this work, an efficient method was designed to achieve highly functionalized aziridine peptidomimetics via a sequential reaction, which involves the organocatalytic aziridination of alpha,beta-unsaturated aldehydes followed by the Passerini multicomponent reaction in an environmentally friendly solvent mixture (ethanol: water). (AU)

FAPESP's process: 17/23867-0 - Organocatalyzed synthesis of aziridine aldehydes and applications in multicomponent reactions
Grantee:Allan Ribeiro da Silva
Support type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 18/09961-7 - Molecular Design, Synthesis, and Trypanocidal Activity of Reversible Covalent Inhibitors of Cruzain Enzyme
Grantee:Deborah Araujo dos Santos
Support type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support type: Research Grants - Research Centers in Engineering Program