Facile synthesis and biological evaluation of assorted indolyl-3-amides and esters from a single, stable carbonyl nitrile intermediate. Issue 14 (1st April 2015)

• Record Type: Journal Article
• Authors: Veale, Clinton G.L.; Edkins, Adrienne L.; de la Mare, Jo-Anne; de Kock, Carmen; Smith, Peter J.; Khanye, Setshaba D.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 14(2015)
• Page Start: 1860
• Page End: 1864
• Publication Date: 2015-04-01
• Subjects: Indole -- Amide -- Ester -- Carbonyl nitrile; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.02.090
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The synthesis of biologically relevant amides and esters is routinely conducted under complex reaction conditions or requires the use of additional catalysts in order to generate sensitive electrophilic species for attack by a nucleophile. Here we present the synthesis of different indolic esters and amides from indolyl-3-carbonyl nitrile, without the requirement of anhydrous reaction conditions or catalysts. Additionally, we screened these compounds for potential in vitro antimalarial and anticancer activity, revealing 1 H -indolyl-3-carboxylic acid 3-(indolyl-3-carboxamide)aminobenzyl ester to have moderate activity against both lines.