TAP-doxorubicin, Super-Leu-Dox, CPI-0004, CPI-004Na, CPI-0004Na
Chemical Name: N-[N-(3-Carboxypropionyl)-beta-alanyl-L-leucyl-L-alanyl-L-leucyl]daunorubicin sodium salt; (8S,10S)-10-[3-[N-(3-Carboxy-1-oxopropyl)-beta-alanyl-L-leucyl-L-alanyl-L-leucylamido]-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyloxy]-8-(hydroxyacetyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione sodium salt
CAS No. 274912-87-7 (free acid)
项目整合开发状态: Preclinical
项目研究机构: Corixa (Originator), Diatos (Licensee), Medarex (Licensee)
合成路线:The condensation of doxorubicin (I) with Fmoc-beta-alanyl-L-leucyl-L-alanyl-L-leucine (II) by means of HATU and DIEA in DMF gives the protected adduct (III),which is treated with piperidine in DMF to yield the deprotected adduct (IV).Finally,this compound is condensed with succinic anhydride (V) in the same solvent and treated with NaOH or NaHCO3 to afford the target sodium salt.
📌 参考资料/链接：
参考文献标题:Prodrug cpds.and process for preparation thereof
文献作者:Lobl,T.J.; Trouet,A.; Fernandez,A.-M.; Nieder,M.H.; Yarranton,G.T.; Gangwar,S.; Viski,P.; Lewis,E.; Dubois,V.(Beckman Coulter,Inc.)
参考来源:WO 0033888
📄 详细内容
合成路线:The condensation of doxorubicin (I) with Fmoc-beta-alanyl-L-leucyl-L-alanyl-L-leucine (II) by means of HATU and DIEA in DMF gives the protected adduct (III),which is treated with piperidine in DMF to yield the deprotected adduct (IV).Finally,this compound is condensed with succinic anhydride (V) in the same solvent and treated with NaOH or NaHCO3 to afford the target sodium salt.
参考文献标题:N-Succinyl-(beta-alanyl-L-leucyl-L-alanyl-L-leucyl)doxorubicin: An extracellularly tumor-activated prodrug devoid of intravenous acute toxicity
文献作者:Fernandez,A.-M.; Van Derpoorten,K.; Dasnois,L.; Lebtahi,K.; Dubois,V.; Lobl,T.J.; Gangwar,S.; Oliyai,C.; Lewis,E.R.; Shochat,D.; Trouet,A.
参考来源:J Med Chem 2001,44(22),3750