WMC-79

Chemical Name: 5-Nitro-2-[3-[4-[3-(6-oxo-6H-imidazo[4,5,1-de]acridin-5-ylamino)propyl]piperazin-1-yl]propyl]benzo[de]isoquinoline-1,3(2H)-dione
CAS No. 359630-61-8
项目整合开发状态: Preclinical
项目研究机构: National Cancer Institute (Originator)
合成路线:2,6-Dichloro-3-nitrobenzoic acid (I) was condensed with aniline (II) to produce the anilinobenzoic acid (III),which was subsequently cyclized to the acridinone (IV) upon treatment with POCl3.Displacement of the chloride group of (IV) with 1,4-bis(3-aminopropyl)piperazine (V) in DMF afforded adduct (VI).The nitro group of (VI) was reduced by catalytic hydrogenation in the presence of Raney-Ni and formic acid,and the intermediate formamide was further cyclized under acidic conditions to the imidazoacridinone (VII).Finally,conversion of the primary amino group of (VII) to the target imide was achieved by heating with 3-nitro-1,8-naphthalenedicarboxylic anhydride (VIII) in DMF.