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【结 构 式】 
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【药物名称】QYL-972 【化学名称】2(S)-[2-[(Z)-2-Amino-6-methoxy-9H-purin-9-ylmethylene]cyclopropylmethoxy(phenoxy)phosphorylamino]propionic acid methyl ester 【CA登记号】 【 分 子 式 】C21H25N6O6P 【 分 子 量 】488.4438 |
【开发单位】University of Alabama at Birmingham (Originator), Wayne State University (Originator) 【药理作用】Anti-Cytomegalovirus Drugs, ANTIINFECTIVE THERAPY, Antiviral Drugs, Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems |
合成路线1
The reaction of 6-chloro-9-[2-(hydroxymethyl)cyclopropylidenemethyl]purine-2-amine (I) with methanol and K2CO3 gives of 9-[2-(hydroxymethyl)cyclopropylidenemethyl]-6-methoxypurine-2-amine (II) which is then condensed with the phosphorylated L-alanine ester (III) by means of N-methylimidazole (NMI) in pyridine/THF. The intermediate the phosphorylated L-alanine ester (III) has been obtained by condensation of L-alanine methyl ester (IV) with phenyl dichlorophosphate (V) by means of TEA in dichloromethane.
| 【1】 Kern, E.R.; Qiu, Y.-L.; Ptak, R.G.; Breitenbach, J.M.; Zemlicka, J.; Drach, J.C.; Cheng, Y.-C.; Lin, J.-S.; Synthesis and antiviral activity of phosphoralaninate derivatives of methylenecyclopropane analogues of nucleosides. Antivir Res 1999, 43, 1, 37. |
| 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) | 41415 | [2-[(Z)-(2-amino-6-chloro-9H-purin-9-yl)methylidene]cyclopropyl]methanol | C10H10ClN5O | 详情 | 详情 | |
| (II) | 41416 | [2-[(Z)-(2-amino-6-methoxy-9H-purin-9-yl)methylidene]cyclopropyl]methanol | C11H13N5O2 | 详情 | 详情 | |
| (III) | 41417 | methyl (2S)-2-[[chloro(phenoxy)phosphoryl]amino]propanoate | C10H13ClNO4P | 详情 | 详情 | |
| (IV) | 20694 | methyl (2S)-2-aminopropanoate | C4H9NO2 | 详情 | 详情 | |
| (V) | 39640 | Phenyl dichlorophosphate;phenyl phosphorodichloridate | 770-12-7 | C6H5Cl2O2P | 详情 | 详情 |