MX-7091

Chemical Name: 5-[6-[3-(1-Adamantyl)-4-hydroxyphenyl]pyridin-3-ylmethylene]thiazolidine-2,4-dione
CAS No. 459422-71-0
项目整合开发状态: Preclinical
项目研究机构: Maxia (Originator)
合成路线:Coupling between 4-bromophenol (I) and 1-adamantanol (II) in the presence of H2SO4 affords the adamantanyl phenol (III),which is further protected as the silyl ether (IV) by means of t-butyldimethylsilyl chloride and DMAP.Addition of triisopropyl borate to the organolithium derivative of (IV) gives rise,after aqueous quenching,to the boronic acid (V).Then,Suzuki coupling of boronic acid (V) with 6-bromopyridine-3-carbaldehyde (VI) furnishes the phenylpyridine adduct (VII).Desilylation of (VII) to provide phenol (VIII) is accomplished by treatment with tetrabutylammonium fluoride in THF.Finally,condensation of pyridine aldehyde (VIII) with 2,4-thiazolidinedione (IX) under Knoevenagel conditions provides the target compound