CP-0467

Chemical Name: 7-[2-(5-Amino-1,2,4-thiadiazol-4-yl)-2(Z)-(methoxyimino)acetamido]-3-(benzothiazol-2-ylthio)-3-cephem-4-carboxylic acid sodium salt
项目整合开发状态: Preclinical
项目研究机构: Meiji Seika (Originator)
合成路线:The substitution of the triflate group of (I) by the sodium thiolate (II) provided a mixture of 3-cephem (III) and 2-cephem (IV) compounds.Without purification,treatment of the mixture with m-chloroperbenzoic acid gave the corresponding S-oxides,which were reduced with PCl3 to yield the 3-cephem (III).The phenylacetyl group was removed by treatment with PCl5 and pyridine,followed by hydrolysis with MeOH to afford amine (V).Acylation with acid (VI) in the presence of dicyclohexyl carbodiimide (DCC) and 1-hydroxybenzotriazole (HOBT) yielded amide (VII).Then,removal of the benzhydryl protecting group using trifluoroacetic acid and anisole,followed by treatment with aqueous NaHCO3 provided the target cephalosporin.
📌 参考资料/链接:
参考文献标题:Novel cephalosporin derivatives possessing a bicyclic heterocycle at the 3-position.Part I: Synthesis and biological activities of 3-(benzothiazol-2-yl)thiocephalosporin derivatives,CP0467 and related compounds
文献作者:Tsushima,M.; Iwamatsu,K.; Tamura,A.; Shibahara,S.
参考来源:Bioorg Med Chem 1998,6(7),1009