新产品编号:1667937
Chemical Name: N-[1(S)-Benzyl-3-[2-[5-(3-cyanophenyl)-2-thienylsulfonamido]ethylamino]-2,3-dioxopropyl]-2,6-dichlorobenzamide
项目整合开发状态: Biological Testing
项目研究机构: Cephalon (Originator)
合成路线:Ethylenediamine (I) was selectively monoprotected as the N-Boc derivative (II) and then coupled with sulfonyl chloride (III),yielding sulfonamide (IV).After deprotection of the Boc group of (IV) with HCl in dioxan,the resulting amine (V) was condensed with hydroxyacid (VI) by means of BOP reagent to give amide (VII).Acid deprotection of the Boc group of (VII),followed by condensation with 2,6-dichlorobenzoyl chloride (IX),provided (X).Finally,the hydroxyl group of (X) was oxidized to the title ketone employing the Dess-Martin periodinane reagent in CH2Cl2.
📌 参考资料/链接：
参考文献标题:Peptidyl-containing alpha-ketoamide cysteine and serine protease inhibitors
文献作者:Wells,G.J.; Mallamo,J.P.; Chatterjee,S.; Bihovsky,R.(Cephalon,Inc.)
参考来源:US 6150378
📄 详细内容
合成路线:Ethylenediamine (I) was selectively monoprotected as the N-Boc derivative (II) and then coupled with sulfonyl chloride (III),yielding sulfonamide (IV).After deprotection of the Boc group of (IV) with HCl in dioxan,the resulting amine (V) was condensed with hydroxyacid (VI) by means of BOP reagent to give amide (VII).Acid deprotection of the Boc group of (VII),followed by condensation with 2,6-dichlorobenzoyl chloride (IX),provided (X).Finally,the hydroxyl group of (X) was oxidized to the title ketone employing the Dess-Martin periodinane reagent in CH2Cl2.
参考文献标题:P2-Achiral,P'-extended alpha-ketoamide inhibitors of calpain I
文献作者:Chatterjee,S.; Dunn,D.; Tao,M.; Wells,G.; Gu,Z.Q.; Bihovsky,R.; Ator,M.A.; Siman,R.; Mallamo,J.P.
参考来源:Bioorg Med Chem Lett 1999,9(16),2371