A-289099
Chemical Name: 1-Methyl-5-[5(S)-(3,4,5-trimethoxyphenyl)-4,5-dihydrooxazol-2-yl]-1H-indole
项目整合开发状态: Preclinical
项目研究机构: Abbott (Originator)
合成路线:Enantioselective dihydroxylation of styrene (I) using AD-mix-alpha gave the (S)-diol (II).Tosylation of the primary hydroxyl group of (II),followed by nucleophilic displacement of the tosylate (III) with NaN3,provided azido alcohol (IV).The azido group of (IV) was then reduced to the corresponding amine (V) by catalytic hydrogenation in the presence of Pd/C.Finally,condensation of the chiral amino alcohol (V) with 1-methyl-5-cyanoindole (VI) in a hot mixture of ethylene glycol and glycerol yielded the target diaryl oxazolidine.
📌 参考资料/链接:
参考文献标题:Synthesis and biological evaluation of 2-indolyloxazolines as a new class of tubulin polymerization inhibitors.Discovery of A-289099 as an orally active antitumor agent
文献作者:Li,Q.; Woods,K.W.; Claiborne,A.; Gwaltney,S.L.II; Barr,K.J.; Liu,G.; Gehrke,L.; Credo,R.B.; Hui,Y.H.; Lee,J.; Warner,R.B.; Kovar,P.; Nukkala,M.A.; Zielinski,N.A.; Tahir,S.K.; Fitzgerald,M.; Kim,K.H.; Marsh,K.; Frost,D.; et al.
参考来源:Bioorg Med Chem Lett 2002,12(3),465