NR58.4
Chemical Name: N-[2,6-Dioxopiperidin-3(S)-yl]-10-undecenamide
CAS No. 284495-31-4
项目整合开发状态: Preclinical
项目研究机构: NeoRx (Originator)
合成路线:The title compound was prepared by two related procedures.The acylation of L-glutamine (I) with 10-undecenoyl chloride (II) under Schotten-Baumann conditions afforded N-undecenoylglutamine (III).This was then cyclized to the title glutarimide derivative by treatment with dicyclohexylcarbodiimide and N-hydroxysuccinimide.
合成路线:In an alternative synthesis,(S)-3-(tert-butoxycarbonylamino)glutarimide (IV) was deprotected by means of trifluoroacetic acid to yield the aminoglutarimide (V).BOP-mediated coupling of (V) with 10-undecenoic acid (VI) then gave the target amide.
📌 参考资料/链接：
参考文献标题:Cpds.and methods to inhibit or augment an inflammatory response
文献作者:Grainger,D.J.; Tatalick,L.M.(NeoRx Corp.)
参考来源:WO 0042071
📄 详细内容
合成路线:The title compound was prepared by two related procedures.The acylation of L-glutamine (I) with 10-undecenoyl chloride (II) under Schotten-Baumann conditions afforded N-undecenoylglutamine (III).This was then cyclized to the title glutarimide derivative by treatment with dicyclohexylcarbodiimide and N-hydroxysuccinimide.
合成路线:In an alternative synthesis,(S)-3-(tert-butoxycarbonylamino)glutarimide (IV) was deprotected by means of trifluoroacetic acid to yield the aminoglutarimide (V).BOP-mediated coupling of (V) with 10-undecenoic acid (VI) then gave the target amide.
参考文献标题:Design,synthesis,and preliminary pharmacological evaluation of N-acyl-3-aminoglutarimides as broad-spectrum chemokine inhibitors in vitro and anti-inflammatory agents in vivo
文献作者:Fox,D.J.; Reckless,J.; Warren,S.G.; Grainger,D.J.
参考来源:J Med Chem 2002,45(2),360