199609-69-3Relevant academic research and scientific papers
Monoaryl- and bisaryldihydroxytropolones as potent inhibitors of inositol monophosphatase
Piettre, Serge R.,André, Catherine,Chanal, Marie-Christine,Ducep, Jean-Bernard,Lesur, Brigitte,Piriou, Fran?ois,Raboisson, Pierre,Rondeau, Jean-Michel,Schelcher, Charles,Zimmermann, Pascale,Ganzhorn, Axel J.
, p. 4208 - 4221 (2007/10/03)
The first successful preparation of mono- and disubstituted 3,7- dihydroxytropolone involves a four-step synthetic scheme. Thus, bromination of 3,7-dihydroxytropolone (8) followed by permethylation of the resultant products furnished gram quantities of intermediates 13-18. Single or double Suzuki coupling reactions between these permethylated monobromo- and dibromodihydroxytropolone derivatives and a variety of boronic acids delivered the expected products whose deprotection yielded the desired compounds 1a-u and 26a-n, usually in fair to good yields. Tropolones 1 and 26 were found to be potent inhibitors of inositol monophosphatase with IC50 values in the low-micromolar range. The results are discussed in the context of the recently described novel mode of inhibition of the enzyme by 3,7- dihydroxytropolones.
