SNO-Yohimbine, S-Nitrosylated yohimbine, NMI-187

Chemical Name: (1R,2S,4aR,13bS,14aS)-13-Acetyl-2-[3-methyl-3-(nitrososulfanyl)butanoyloxy]-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydrobenz[g]indolo[2,3-a]quinolizine-1-carboxylic acid methyl ester
项目整合开发状态: Preclinical
项目研究机构: NitroMed (Originator)
合成路线:3-Mercapto-3-methylbutyric acid (I) was protected as the tetrahydropyranyl derivative (III) using dihydropyran (II) and HCl.Subsequent treatment of (III) with triphosgene and triethylamine generated the acid anhydride (IV).Condensation of yohimbine (V) with anhydride (IV) in the presence of dimethylaminopyridine provided ester (VI).Further acetylation of (VI) with acetyl chloride in acetic acid gave rise to the N,S-diacetyl compound (VII),which was selectively deacetylated with mercuric trifluoroacetate,yielding thiol (VIII).Finally,reaction of (VIII) with NaNO2 and HCl furnished the corresponding S-nitrosyl derivative.