Diastereoselective multicomponent synthesis and anti-HSV-1 evaluation of dihydrofuran-fused derivatives

Angela Scala, Massimiliano Cordaro, Francesco Risitano, Ivana Colao, Assunta Venuti, Maria Teresa Sciortino, Patrizia Primerano, Giovanni Grassi

Research output: Contribution to journalArticlepeer-review

Abstract

Enolizable 6-membered cyclic 1,3-dicarbonyls undergo an efficient and diastereoselective domino condensation/addition/heterocyclization reaction with arylaldehydes and phenacyl chloride, producing highly substituted dihydrofuran-fused derivatives. Ring size of the cyclic 1,3-dicarbonyls and the presence of at least one keto group are crucial to the reaction's success. The new compounds were evaluated in vitro for antiviral activity against herpes simplex virus type-1 (HSV-1). Interestingly, some of them appeared able to interfere with HSV-1 replication, without detection of cytotoxic effects.

Original languageEnglish
Pages (from-to)325-333
Number of pages9
JournalMolecular Diversity
Volume16
Issue number2
DOIs
Publication statusPublished - May 2012

Keywords

  • Antiviral activity
  • Cyclic 1,3-dicarbonyls
  • Cyclization
  • Diastereoselectivity
  • Multicomponent reaction

ASJC Scopus subject areas

  • Molecular Biology
  • Drug Discovery
  • Information Systems
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Catalysis
  • Organic Chemistry

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