HKI-9924129
Chemical Name: (2S,5R,6R)-6-[2(R)-[Nalpha,Nepsilon-Bis(2,3-diacetoxybenzoyl)-L-lysyl-Ngamma-(benzoyloxy)-Ngamma-methyl-L-glutaminylamino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt
项目整合开发状态: Preclinical
项目研究机构: Gr黱enthal (Originator), Hans Kn鰈l Institute Natural Prod. Res. (Originator)
合成路线:Catalytic hydrogenolysis of benzyl ester (VII) affords carboxylic acid (VIII) (1).Then,coupling of acid (VIII) with ampicillin (IX) using isobutyl chloroformate provides the target adduct,which is finally converted to the title sodium salt upon treatment with sodium 2-ethylhexanoate in EtOAc.
📌 参考资料/链接：
参考文献标题:Siderophore antibiotic conjugates with tetra- or hexadentate iron chelators on the basis of amino acids or peptides,method for producing them and the use thereof
文献作者:Heinisch,L.; M鰈lmann,U.; Wittmann,S.(Gr黱enthal GmbH)
参考来源:DE 10111163; WO 0270017
📄 详细内容
合成路线:Acylation of L-lysine (I) with 2,3-diacetoxybenzoyl chloride (II) provides the dibenzoyl lysine derivative (III).After activation of (III) as the corresponding mixed anhydride with isobutyl chloroformate,condensation with alpha-benzyl L-glutamate (IV) yields the dipeptide compound (V).This is further coupled with N-(benzoyloxy) methylamine (VI),via the mixed anhydride with isobutyl chloroformate,to furnish hydroxamate (VII).
合成路线:Catalytic hydrogenolysis of benzyl ester (VII) affords carboxylic acid (VIII) (1).Then,coupling of acid (VIII) with ampicillin (IX) using isobutyl chloroformate provides the target adduct,which is finally converted to the title sodium salt upon treatment with sodium 2-ethylhexanoate in EtOAc.
参考文献标题:New synthetic siderophores and their beta-lactam conjugates based on diamino acids and dipeptides
文献作者:Wittmann,S.; Schnabelrauch,M..; Scherlitz-Hofmann,I.; Mollmann,U.; Ankel-Fuchs,D.; Heinisch,L.
参考来源:Bioorg Med Chem 2002,10(6),1659