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MnTE-2-PyP5+, AEOL-10113

Chemical Name: (SP-4-1)-[[2,2',2'',2'''-(21H,23H-Porphine-5,10,15,20-tetrayl-kappaN21,kappaN22,kappaN23,kappaN24)tetrakis[1-ethylpyridiniumato]](2-)]manganese(5+)
CAS No. 223723-79-3, 219818-60-7 (chloride), 223723-80-6 (hexafluorophosphate salt)
项目整合开发状态: Preclinical
项目研究机构: Duke University (Originator), Aeolus Pharmaceuticals (Licensee)
合成路线:Tetrakis-(2-pyridyl)porphyrin (III) was prepared by condensation between pyridine-2-carboxaldehyde (I) and pyrrole (II) in refluxing propionic acid.Metallation of porphyrin (III) was performed with MnCl2,which spontaneously underwent oxidation,yielding the Mn3+ complex (IV).Subsequent N-alkylation of the pyridine rings with ethyl iodide produced the corresponding pyridinium iodide salt,which was transformed to the analogous chloride by treatment with tetrabutylammonium chloride (1).In an alternative procedure,initial quaternization of the pyridine rings of porphyrin (III) with ethyl p-toluenesulfonate afforded (V),which was further metallated with MnCl2 to give the title compound.
📌 参考资料/链接:
参考文献标题:Substd.porphyrins
文献作者:Batinic-Haberle,I.; Fridovich,I.(Duke University)
参考来源:EP 1045851; JP 2001521939; WO 9923097

📄 详细内容


合成路线:Tetrakis-(2-pyridyl)porphyrin (III) was prepared by condensation between pyridine-2-carboxaldehyde (I) and pyrrole (II) in refluxing propionic acid.Metallation of porphyrin (III) was performed with MnCl2,which spontaneously underwent oxidation,yielding the Mn3+ complex (IV).Subsequent N-alkylation of the pyridine rings with ethyl iodide produced the corresponding pyridinium iodide salt,which was transformed to the analogous chloride by treatment with tetrabutylammonium chloride (1).In an alternative procedure,initial quaternization of the pyridine rings of porphyrin (III) with ethyl p-toluenesulfonate afforded (V),which was further metallated with MnCl2 to give the title compound.

参考文献标题:Manganese-porphyrin reactions with lipid and lipoproteins
文献作者:Bloodsworth,A.; et al.
参考来源:Free Radical Biol Med 2000,28(7),1017


合成路线:Tetrakis-(2-pyridyl)porphyrin (III) was prepared by condensation between pyridine-2-carboxaldehyde (I) and pyrrole (II) in refluxing propionic acid.Metallation of porphyrin (III) was performed with MnCl2,which spontaneously underwent oxidation,yielding the Mn3+ complex (IV).Subsequent N-alkylation of the pyridine rings with ethyl iodide produced the corresponding pyridinium iodide salt,which was transformed to the analogous chloride by treatment with tetrabutylammonium chloride (1).In an alternative procedure,initial quaternization of the pyridine rings of porphyrin (III) with ethyl p-toluenesulfonate afforded (V),which was further metallated with MnCl2 to give the title compound.

参考文献标题:Relationships among redox potentials,proton dissociation constants of pyrrolic nitrogens,and in vivo and in vitro superoxide dismutating activities of magnase(III) and iron(III) water-soluble porphyrins
文献作者:Batini?Haberle,I.; et al.
参考来源:Inorg Chem 1999,38(18),4011


合成路线:Tetrakis-(2-pyridyl)porphyrin (III) was prepared by condensation between pyridine-2-carboxaldehyde (I) and pyrrole (II) in refluxing propionic acid.Metallation of porphyrin (III) was performed with MnCl2,which spontaneously underwent oxidation,yielding the Mn3+ complex (IV).Subsequent N-alkylation of the pyridine rings with ethyl iodide produced the corresponding pyridinium iodide salt,which was transformed to the analogous chloride by treatment with tetrabutylammonium chloride (1).In an alternative procedure,initial quaternization of the pyridine rings of porphyrin (III) with ethyl p-toluenesulfonate afforded (V),which was further metallated with MnCl2 to give the title compound.
参考文献标题:Synthesis and superoxide dismuting activities of partially (1-4) beta-chlorinated derivatives of manganese (III) meso-tetrakis (N-ethylpyridinium-2-yl)porphyrin
文献作者:Kachadourian,R.; et al.
参考来源:Inorg Chem 1999,38(2),391


产品链接: CAS No.219818-60-7››