新产品编号:1601493
Chemical Name: N-(5-Bromopyridin-3-ylcarbonyl)-3-(cyclohexyl)-L-alanyl-L-arginyl-L-phenylalanylamide
项目整合开发状态: Biological Testing
项目研究机构: Millennium (Originator), R.W. Johnson (Originator)
合成路线:The compound was prepared via solid-phase synthesis using Rink-amide resin (I).After initial Fmoc-deprotection of (I) with piperidine in DMF,Fmoc-L-phenylalanine (II) was coupled to the resin by means of N,N'-diisopropyl carbodiimide (DIC) and hydroxybenzotriazole (HOBt) in DMF,yielding the phenylalanine-linked resin (III).Subsequent Fmoc-deprotection and coupling cycles with protected arginine (IV) and cyclohexylalanine (VI) produced the peptide resins (V) and (VII),respectively.Further deprotection of (VII) with piperidine,followed by coupling with 5-bromonicotinic acid (VIII) gave the corresponding amide (IX).Cleavage of the final peptide amide from the resin (IX) was then accomplished by treatment trifluoroacetic acid and anisole.
📌 参考资料/链接：
参考文献标题:Substd.heterocyclic acyl-tripeptides useful as thrombin receptor modulators
文献作者:Hawkins,M.J.; Maryanoff,B.E.; McComsey,D.F.(Ortho-McNeil Pharmaceutical,Inc.)
参考来源:WO 0035942
📄 详细内容
合成路线:The compound was prepared via solid-phase synthesis using Rink-amide resin (I).After initial Fmoc-deprotection of (I) with piperidine in DMF,Fmoc-L-phenylalanine (II) was coupled to the resin by means of N,N'-diisopropyl carbodiimide (DIC) and hydroxybenzotriazole (HOBt) in DMF,yielding the phenylalanine-linked resin (III).Subsequent Fmoc-deprotection and coupling cycles with protected arginine (IV) and cyclohexylalanine (VI) produced the peptide resins (V) and (VII),respectively.Further deprotection of (VII) with piperidine,followed by coupling with 5-bromonicotinic acid (VIII) gave the corresponding amide (IX).Cleavage of the final peptide amide from the resin (IX) was then accomplished by treatment trifluoroacetic acid and anisole.
参考文献标题:Heterocycle-peptide hybrid compounds.Aminotriazole-containing agonists of the thrombin receptor (PAR-1)
文献作者:McComsey,D.F.; Hawkins,M.J.; Andrade-Gordon,P.; Addo,M.F.; Oksenberg,D.; Maryanoff,B.E.
参考来源:Bioorg Med Chem Lett 1999,9(10),1423