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 journalArticle

19 Citations (Scopus)

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

Fingerprint

Human Herpesvirus 1
viruses
Viruses
Derivatives
Addition reactions
evaluation
synthesis
Virus Replication
Antiviral Agents
Chlorides
Condensation
condensation
chlorides
rings
In Vitro Techniques

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

Cite this

Scala, A., Cordaro, M., Risitano, F., Colao, I., Venuti, A., Sciortino, M. T., ... Grassi, G. (2012). Diastereoselective multicomponent synthesis and anti-HSV-1 evaluation of dihydrofuran-fused derivatives. Molecular Diversity, 16(2), 325-333. https://doi.org/10.1007/s11030-012-9367-0

Diastereoselective multicomponent synthesis and anti-HSV-1 evaluation of dihydrofuran-fused derivatives. / Scala, Angela; Cordaro, Massimiliano; Risitano, Francesco; Colao, Ivana; Venuti, Assunta; Sciortino, Maria Teresa; Primerano, Patrizia; Grassi, Giovanni.

In: Molecular Diversity, Vol. 16, No. 2, 05.2012, p. 325-333.

Research output: Contribution to journalArticle

Scala, A, Cordaro, M, Risitano, F, Colao, I, Venuti, A, Sciortino, MT, Primerano, P & Grassi, G 2012, 'Diastereoselective multicomponent synthesis and anti-HSV-1 evaluation of dihydrofuran-fused derivatives', Molecular Diversity, vol. 16, no. 2, pp. 325-333. https://doi.org/10.1007/s11030-012-9367-0
Scala, Angela ; Cordaro, Massimiliano ; Risitano, Francesco ; Colao, Ivana ; Venuti, Assunta ; Sciortino, Maria Teresa ; Primerano, Patrizia ; Grassi, Giovanni. / Diastereoselective multicomponent synthesis and anti-HSV-1 evaluation of dihydrofuran-fused derivatives. In: Molecular Diversity. 2012 ; Vol. 16, No. 2. pp. 325-333.
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