SJA-6017
钙蛋白酶抑制剂VIChemical Name: 4-Fluorophenylsulfonyl-L-valyl-L-leucinal
CAS No. 190274-53-4
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator), Senju (Originator)
合成路线:The condensation of L-valine (I) with 4-fluorobenzenesulfonyl chloride (II) by means of NaOH in THF/water gives N-(4-fluorobenzenesulfonyl)-L-valine (III),which is esterified with N-hydroxysuccinimide (IV) by means of EDC in dichloromethane to yield the activated ester (V).The condensation of (V) with L-leucinol (VI) by means of TEA in dichloromethane affords the N-(4-fluorobenzenesulfonyl)-L-valyl-L-leucinol (VII),which is finally oxidized with the SO3/Pyridine complex in DMSO/dichloromethane to provide the target leucinal derivative.
📌 参考资料/链接：
参考文献标题:Angiogenesis inhibitor
文献作者:Fukiage,C.; Azuma,M.; Inoue,J.; Nakamura,M.; Yoshida,Y.(Senju Pharmaceuticals Co.,Ltd.)
参考来源:EP 0771565; EP 0927716; EP 0928786; JP 1998147564; JP 1998147566; JP 2001233847; US 6057290; US 6214800
📄 详细内容
合成路线:The condensation of L-valine (I) with 4-fluorobenzenesulfonyl chloride (II) by means of NaOH in THF/water gives N-(4-fluorobenzenesulfonyl)-L-valine (III),which is esterified with N-hydroxysuccinimide (IV) by means of EDC in dichloromethane to yield the activated ester (V).The condensation of (V) with L-leucinol (VI) by means of TEA in dichloromethane affords the N-(4-fluorobenzenesulfonyl)-L-valyl-L-leucinol (VII),which is finally oxidized with the SO3/Pyridine complex in DMSO/dichloromethane to provide the target leucinal derivative.
参考文献标题:SJA6017,a newly synthesized peptide aldehyde inhibitor of calpain: amelioration of cataract in cultured rat lenses
文献作者:Fukiage,C.; Azuma,M.; Nakamura,Y.; Tamada,Y.; Nakamura,M.; Shearer,T.R.
参考来源:Biochim Biophys Acta 1997,1361(3),304
产品链接: CAS No. 190274-53-4››