Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer.
Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane ((-)-BPAP), which is a highly potent and selective catecholaminergic activity enhancer (CAE) substance, are described. The synthetic approach consists of the coupling reaction of benzofuran with (R)-N-tosyl-2-propylazirizine or (R)-N-methoxy-N-methylnorvaliamide, followed by appropriate modifications of the resulting coupling products. As the results, (-)-BPAP turned out to have the R configuration, which was finally confirmed by X-ray crystallographic analysis.
Oka
T
T
Research Institute, Fujimoto Pharmaceutical Corporation, 1-3-40, Nishiotsuka, Matsubara, Osaka 580-8503, Japan. soyaku@fujumoto-pharm.co.jp
Yasusa
T
T
Ando
T
T
Watanabe
M
M
Yoneda
F
F
Ishida
T
T
Knoll
J
J
D001389:Azirines / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D002395:Catecholamines / Q000819:agonists* / Q000378:metabolism; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
C404200:1-(benzofuran-2-yl)-2-propylaminopentane; D001389:Azirines; D001572:Benzofurans; D002395:Catecholamines; C105430:benzofuran