NM-3

2-(8-羟基-6-甲氧基-1-氧代异苯并吡喃-3-基)丙酸Chemical Name: 2-(8-Hydroxy-6-methoxy-1-oxo-1H-2-benzopyran-3-yl)propionic acid
CAS No. 181427-78-1
项目整合开发状态: Phase I/II
项目研究机构: Mercian (Supplier), Ilex Oncology (Proprietary), Microbial Chemistry Research Foundation (Originator)
合成路线:Chlorination of cytogenin (I) using carbon tetrachloride and triphenylphosphine provided chloride (II).Subsequent displacement of the halogen atom of (II) by NaCN afforded nitrile (III).In an alternative procedure,the isocoumarin (IV) was protected as the acetate ester (V) and then brominated to (VI) employing N-bromosuccinimide.After deprotection of the acetate ester of (VI),displacement by KCN yielded nitrile (III).The hydroxyl group of (III) was then silylated by means of tert-butyldimethylsilyl chloride and imidazole to give (VIII).Subsequent alkylation of (VIII) with methyl iodide under phase-transfer conditions furnished the alpha-methyl nitrile (IX).Finally,acid hydrolysis of the nitrile group of (IX) with concomitant desilylation provided the title compound.