title: Aldol-type compounds from water-soluble indole-3,4-diones: synthesis, kinetics, and antiviral properties.
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.
authors: CNR-ISMN Istituto per lo Studio dei Materiali Nanostrutturati, V.le F. Stagno D'Alcontres 31, 98166 , Messina, Italy.
authors: Angela
authors: A
authors: Scala
authors: Massimiliano
authors: M
authors: Cordaro
authors: Antonino
authors: A
authors: Mazzaglia
authors: Francesco
authors: F
authors: Risitano
authors: Assunta
authors: A
authors: Venuti
authors: Maria Teresa
authors: MT
authors: Sciortino
authors: Giovanni
authors: G
authors: Grassi
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology*; D018844:Cyclin-Dependent Kinases / Q000037:antagonists & inhibitors; D015195:Drug Design; D006561:Herpes Simplex / Q000188:drug therapy*; D018259:Herpesvirus 1, Human / Q000187:drug effects*; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology*
chemical_list: D000447:Aldehydes; D000998:Antiviral Agents; D007211:Indoles; D018844:Cyclin-Dependent Kinases
references: Chem Rev. 2012 Jun 13;112(6):3193-328
references: 22480243
references: J Org Chem. 2013 Apr 19;78(8):3972-9
references: 23506161
references: Antivir Ther. 2009;14(8):1051-64
references: 20032535
references: Nat Rev Drug Discov. 2002 Jan;1(1):13-25
references: 12119605
references: J Phys Chem A. 2008 Apr 3;112(13):2827-37
references: 18314969
references: Antivir Chem Chemother. 2006;17(6):293-320
references: 17249245
references: Mol Divers. 2012 May;16(2):325-33
references: 22528269
references: Trends Pharmacol Sci. 2002 Sep;23(9):417-25
references: 12237154
references: J Virol. 2007 Oct;81(20):10924-32
references: 17670820
references: Curr Med Chem. 2008;15(9):900-11
references: 18473797