Aldol-type compounds from water-soluble indole-3,4-diones: Synthesis, kinetics, and antiviral properties

Angela Scala, Massimiliano Cordaro, Antonino Mazzaglia, Francesco Risitano, Assunta Venuti, Maria Teresa Sciortino, Giovanni Grassi

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A straightforward transformation of indole-3,4-diones is reported. The reaction feasibility is evidenced by kinetic studies on a model substrate, revealing a double phase process with a first faster pseudo-first-order step (i.e., deprotonation of the dione and self-nucleophilic attack of the anion) and a subsequent slower dehydration of the intermediate. The overall process is faster at pH higher than the pK value of the investigated substrate. The biological relevance of new compounds has been assessed in vitro against herpes simplex virus type-1 (HSV-1), showing a more promising biological profile with respect to their precursors.

Original languageEnglish
Pages (from-to)479-488
Number of pages10
JournalMolecular Diversity
Volume17
Issue number3
DOIs
Publication statusPublished - Aug 2013

Fingerprint

indoles
Human Herpesvirus 1
Dione
Dehydration
Antiviral Agents
Anions
Deprotonation
Kinetics
Water
kinetics
viruses
Substrates
synthesis
Viruses
dehydration
water
attack
Negative ions
anions
profiles

Keywords

  • Aldol condensation
  • Antiviral activity
  • Indoledione
  • Kinetics

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., Mazzaglia, A., Risitano, F., Venuti, A., Sciortino, M. T., & Grassi, G. (2013). Aldol-type compounds from water-soluble indole-3,4-diones: Synthesis, kinetics, and antiviral properties. Molecular Diversity, 17(3), 479-488. https://doi.org/10.1007/s11030-013-9448-8

Aldol-type compounds from water-soluble indole-3,4-diones : Synthesis, kinetics, and antiviral properties. / Scala, Angela; Cordaro, Massimiliano; Mazzaglia, Antonino; Risitano, Francesco; Venuti, Assunta; Sciortino, Maria Teresa; Grassi, Giovanni.

In: Molecular Diversity, Vol. 17, No. 3, 08.2013, p. 479-488.

Research output: Contribution to journalArticle

Scala, A, Cordaro, M, Mazzaglia, A, Risitano, F, Venuti, A, Sciortino, MT & Grassi, G 2013, 'Aldol-type compounds from water-soluble indole-3,4-diones: Synthesis, kinetics, and antiviral properties', Molecular Diversity, vol. 17, no. 3, pp. 479-488. https://doi.org/10.1007/s11030-013-9448-8
Scala, Angela ; Cordaro, Massimiliano ; Mazzaglia, Antonino ; Risitano, Francesco ; Venuti, Assunta ; Sciortino, Maria Teresa ; Grassi, Giovanni. / Aldol-type compounds from water-soluble indole-3,4-diones : Synthesis, kinetics, and antiviral properties. In: Molecular Diversity. 2013 ; Vol. 17, No. 3. pp. 479-488.
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