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【结 构 式】 
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【药物名称】HPH-Pep 【化学名称】N,N'-(Pyridin-2,6-diyl)bis(carbonyl)bis(L-histidine) dimethyl diester 【CA登记号】185031-56-5, 346607-04-3 (hydrate) 【 分 子 式 】C21H23N7O6 【 分 子 量 】469.46076 |
【开发单位】Kumamoto University (Originator), Kyoto Prefectural University of Medicine (Originator), Osaka Prefecture University (Originator) 【药理作用】Oncolytic Drugs |
合成路线1
The title compound has been prepared by two related procedures. 2,6-Pyridinedicarboxylic acid (I) was condensed with L-histidine methyl ester (II) using diphenyl phosphoryl azide as the coupling reagent to afford the target diamide.
| 【1】 Otsuka, M.; et al.; An artificial Cu(II) complex with intriguing oxygen radical-quenching profile. X-ray structure, cytochrome c assay, and ESR study. Bioorg Med Chem 1996, 4, 10, 1703. |
合成路线2
In an alternative process, acid chloride (III) was condensed with histidine (IV) in the presence of KOH in H2O/THF producing de diamide diacid (V), which was then esterified by treatment with SOCl2 in cold methanol.
| 【1】 You, J.; et al.; Synthesis of new chiral macrocyclic tetraoxo polyamines containing pyridine ring and functional arms. Synth Commun 1999, 29, 14, 2447. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 58575 | Pyridine-2,6-dicarbonyl chloride; Pyridine-2,6-dicarboxylic acid chloride; 2,6-Pyridinedicarbonyl dichloride; 2,6-Pyridinedicarboxylic acid chloride | 3739-94-4 | C7H3Cl2NO2 | 详情 | 详情 |
| (IV) | 58576 | (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid | C6H9N3O2 | 详情 | 详情 | |
| (V) | 58577 | (2S)-2-({[6-({[(1S)-2-hydroxy-1-(1H-imidazol-5-ylmethyl)-2-oxoethyl]amino}carbonyl)-2-pyridinyl]carbonyl}amino)-3-(1H-imidazol-5-yl)propanoic acid | C19H19N7O6 | 详情 | 详情 |