Synthesis of a human urate transporter-1 inhibitor, an arginine vasopressin antagonist, and a 17β-hydroxysteroid dehydrogenase type-3 inhibitor, using ring-expansion of cyclic ketoximes with DIBALH.
Synthesis of three clinical candidates for medicines, a human urate transporter-1 inhibitor, an arginine vasopressin antagonist, and a 17β-hydroxysteroid dehydrogenase type-3 inhibitor, is described. These compounds were synthesized via construction of their 3,4-dihydro-2H-benzo[b][1,4]oxazine, dibenzodiazepine, and dibenzazocine skeletons, respectively, using the reductive ring-expansion reaction of the corresponding bicyclic or tricyclic oximes with diisobutylaluminum hydride.
Graduate School of Pharmaceutical Sciences, Tohoku University.
Hidetsura
H
Cho
Yusuke
Y
Iwama
Kentaro
K
Okano
Hidetoshi
H
Tokuyama
D015067:17-Hydroxysteroid Dehydrogenases / Q000037:antagonists & inhibitors*; D001127:Arginine Vasopressin / Q000037:antagonists & inhibitors*; D060326:Chemistry Techniques, Synthetic; D003984:Dibenzazepines / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D027361:Organic Anion Transporters / Q000037:antagonists & inhibitors*; D027701:Organic Cation Transport Proteins / Q000037:antagonists & inhibitors*; D010091:Oximes / Q000737:chemistry* / Q000494:pharmacology
D003984:Dibenzazepines; D004791:Enzyme Inhibitors; D027361:Organic Anion Transporters; D027701:Organic Cation Transport Proteins; D010091:Oximes; C491241:SLC22A12 protein, human; D001127:Arginine Vasopressin; D015067:17-Hydroxysteroid Dehydrogenases; C476565:17beta-hydroxysteroid dehydrogenase type 3