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【结 构 式】 
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【药物名称】SGI-101 【化学名称】N-(2,6-Dioxopiperidin-3-yl)-3-(4-nitrophenyl)-2-propenamide 【CA登记号】167173-00-4 【 分 子 式 】C14H13N3O5 【 分 子 量 】303.27681 |
【开发单位】Mansoura University (Originator) 【药理作用】Oncolytic Drugs, Antiestrogens |
合成路线1
4-Nitrocinnamic acid (I) was activated as the succinimidyl ester (II) upon treatment with N-hydroxysuccinimide (NHS) and dicyclohexylcarbodiimide (DCC). Subsequent coupling of (II) with L-glutamine (III) afforded the N-acyl glutamine (IV). A second reaction of (IV) with NHS and DCC produced the active ester (V). Finally, thermal cyclization of (V), with concomitant racemization, led to the desired 2,6-piperidinedione.
| 【1】 Hendry, L.B.; Design of drugs involving receptor-ligand-DNA interactions. WO 9514791 . |
| 【2】 Hendry, L.B.; Computer-based design and screening of molecules using DNA interactions. US 5888741 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 34546 | (E)-3-(4-nitrophenyl)-2-propenoic acid | 619-89-6 | C9H7NO4 | 详情 | 详情 |
| (II) | 34547 | 1-[[(E)-3-(4-nitrophenyl)-2-propenoyl]oxy]-2,5-pyrrolidinedione | C13H10N2O6 | 详情 | 详情 | |
| (III) | 24948 | L-glutamine | 56-85-9 | C5H10N2O3 | 详情 | 详情 |
| (IV) | 34548 | (2S)-5-amino-2-[[(E)-3-(4-nitrophenyl)-2-propenoyl]amino]-5-oxopentanoic acid | C14H15N3O6 | 详情 | 详情 | |
| (V) | 34549 | (E)-N-((1S)-4-amino-1-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-4-oxobutyl)-3-(4-nitrophenyl)-2-propenamide | C18H18N4O8 | 详情 | 详情 |
Extended Information