Lys-Spm, ORI-1202
Chemical Name: L-Lysine N-[3-[4-(3-aminopropylamino)butylamino]propyl]amide
CAS No. 134951-06-7
项目整合开发状态: Preclinical
项目研究机构: MediQuest Therapeutics (Originator)
合成路线:Di-Boc-protected L-lysine p-nitrophenyl active ester (I) was coupled to spermine (II),yielding the primary amide (III) along with some by-products.The crude reaction mixture was fully protected using an excess of di-tert-butyl dicarbonate,and the desired compound (IV) was then isolated by column chromatography.Finally,the Boc-protecting groups of (IV) were removed by acidic treatment to provide the title spermine lysinamide.
📌 参考资料/链接：
参考文献标题:Novel polyamine analogues as therapeutic and diagnostic agents
文献作者:Burns,M.R.; O'Day,C.L.; Bergstrom,D.E.; Webb,H.K.; Vermeulin,N.M.J.(Oridigm Corp.)
参考来源:EP 1085011
📄 详细内容
合成路线:The N-hydroxysuccinimide ester of di-carbobenzyloxy-L-lysine (IV) was coupled to spermine (II),yielding amide (V).The N- carbobenzyloxy groups were then deprotected by catalytic hydrogenolysis in the presence of Pearlman抯 catalyst.
参考文献标题:Amino acid/spermine conjugates: Polyamine amides as potent spermidine uptake inhibitors
文献作者:Burns,M.R.; Carlson,C.L.; Vanderwerf,S.M.; Ziemer,J.R.; Weeks,R.S.; Cai,F.; Webb,H.K.; Graminski,G.F.
参考来源:J Med Chem 2001,44(22),3632
合成路线:The N-hydroxysuccinimide ester of di-carbobenzyloxy-L-lysine (IV) was coupled to spermine (II),yielding amide (V).The N- carbobenzyloxy groups were then deprotected by catalytic hydrogenolysis in the presence of Pearlman抯 catalyst.
参考文献标题:Novel lysine-spermine conjugate inhibits polyamine transport and inhibits cell growth when given with DFMO
文献作者:Weeks,R.S.; Vanderwerf,S.M.; Carlson,C.L.; Burns,M.R.; O'Day,C.L.; Cai,F.; Devens,B.H.; Webb,H.K.
参考来源:Exp Cell Res 2000,261(1),293