Novel spiroannulated 3-benzofuranones. Synthesis and inhibition of the human peptidyl prolyl cis/trans isomerase Pin1.
The novel 3H-spiro[1-benzofuran-2-cyclopentan]-3-one skeleton has been made accessible by different routes. One- and two-step protocols lead to tricyclic and tetracyclic benzofuranones 2 and 3, respectively. A four-step synthesis to spirocompound 4 is described. The novel spirocyclic benzofuranones display modest to no inhibition of the human peptidyl prolyl cis/trans isomerase Pin1.
Braun
Manfred
M
Department of Chemistry, University of Düsseldorf, Universitätstr. 1, D-40225 Düsseldorf, Germany. braunm@uni-duesseldorf.de
Hessamian-Alinejad
Anahita
A
de Lacroix
Boris Féaux
BF
Alvarez
Birte Hernandez
BH
Fischer
Gunter
G
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007783:Lactones / Q000737:chemistry; D000072340:NIMA-Interacting Peptidylprolyl Isomerase; D019696:Peptidylprolyl Isomerase / Q000037:antagonists & inhibitors*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D001572:Benzofurans; D007783:Lactones; D000072340:NIMA-Interacting Peptidylprolyl Isomerase; D013141:Spiro Compounds; C000606846:PIN1 protein, human; D019696:Peptidylprolyl Isomerase