Enantioselective Synthesis of γ-Phenyl-γ-amino Vinyl Phosphonates and Sulfones and Their Application to the Synthesis of Novel Highly Potent Antimalarials.
Journal
ACS omega
ISSN: 2470-1343
Titre abrégé: ACS Omega
Pays: United States
ID NLM: 101691658
Informations de publication
Date de publication:
17 Nov 2020
17 Nov 2020
Historique:
received:
20
07
2020
accepted:
16
10
2020
entrez:
23
11
2020
pubmed:
24
11
2020
medline:
24
11
2020
Statut:
epublish
Résumé
Racemic and enantioselective syntheses of γ-phenyl-γ-amino vinyl phosphonates and sulfones have been achieved using Horner-Wadsworth-Emmons olefination of trityl protected α-phenyl-α-amino aldehydes with tetraethyl methylenediphosphonate and diethyl ((phenylsulfonyl)methyl)phosphonate, respectively, without any racemization. The present strategy has also been successfully applied to the synthesis of peptidyl vinyl phosphonate and peptidyl vinyl sulfone derivatives as potential cysteine protease inhibitors of Chagas disease, K11002, with 100% de. The developed synthetic protocol was further utilized to synthesize hybrid molecules consisting of artemisinin as an inhibitor of major cysteine protease falcipain-2 present in the food vacuole of the malarial parasite. The synthesized artemisinin-dipeptidyl vinyl sulfone hybrid compounds showed effective
Identifiants
pubmed: 33225134
doi: 10.1021/acsomega.0c03470
pmc: PMC7675543
doi:
Types de publication
Journal Article
Langues
eng
Pagination
29025-29037Informations de copyright
© 2020 American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
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