One-pot tandem Hurtley–retro-Claisen–cyclisation reactions in the synthesis of 3-substituted analogues of 5-aminoisoquinolin-1-one (5-AIQ), a water-soluble inhibitor …

ECY Woon, PT Sunderland, HA Paine, MD Lloyd…

Index: Woon, Esther C.Y.; Sunderland, Peter T.; Paine, Helen A.; Lloyd, Matthew D.; Thompson, Andrew S.; Threadgill, Michael D. Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 17 p. 5218 - 5227

Full Text: HTML

Citation Number: 7

Abstract

Abstract Poly (ADP-ribose) polymerase-1 (PARP-1) is an important target for drug design for several therapeutic applications. 5-Aminoisoquinolin-1-one (5-AIQ) is a highly water-soluble lead compound; synthetic routes to 3-substituted analogues were explored. Tandem Hurtley coupling of β-diketones with 2-bromo-3-nitrobenzoic acid, retro-Claisen acyl cleavage and cyclisation gave the corresponding 3-substituted 5-nitroisocoumarins. Treatment with ...