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【结 构 式】 
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【药物名称】NU-3108 【化学名称】1-[4,8-Bis(3,4-dimethoxybenzylamino)-6-(2-hydroxypropylamino)pyrimido[5,4-d]pyrimidin-2-ylamino]-2-propanol 【CA登记号】270920-48-4 【 分 子 式 】C30H40N8O6 【 分 子 量 】608.7033 |
【开发单位】University of Newcastle upon Tyne (Originator) 【药理作用】Antineoplastic Enhancing Agents, Modulators of the Therapeutic Activity of Antineoplastic Agents, ONCOLYTIC DRUGS, Drugs Acting on Purine Nucleoside Transporters |
合成路线1
Condensation of 3,4-dimethoxybenzylamine (I) with 3,4-dimethoxybenzaldehyde (II) afforded imine (III), that was subsequently reduced to amine (IV) by means of NaBH4. Reaction of (V) with 2,4,6,8-tetrachloropyridopyrimidine (V) in THF at room temperature produced the 4,8-diamino derivative (VI). The remaining 2- and 6-chloro groups of (VI) were then displaced by aminoalcohol (VII) in boiling THF to furnish adduct (VIII). Finally, selective cleavage of two dimethoxybenzyl groups using trifluoroacetic acid gave rise to the title compound.
| 【1】 Barlow, H.C.; et al.; Resistance-modifying agents. Part 7: 2,6-Disubstituted-4,8-dibenzylaminopyrimido[5,4-d]pyrimidines that inhibit nucleoside transport in the presence of alpha1-acid glycoprotein (AGP). Bioorg Med Chem Lett 2000, 10, 6, 585. |
| 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) | 13920 | (3,4-Dimethoxyphenyl)methanamine; 3,4-Dimethoxybenzylamine; Veratrylamine | 5763-61-1 | C9H13NO2 | 详情 | 详情 |
| (II) | 18304 | 3,4-Dimethoxybenzaldehyde; Veratraldehyde | 120-14-9 | C9H10O3 | 详情 | 详情 |
| (III) | 41393 | (3,4-dimethoxyphenyl)-N-[(E)-(3,4-dimethoxyphenyl)methylidene]methanamine; N-(3,4-dimethoxybenzyl)-N-[(E)-(3,4-dimethoxyphenyl)methylidene]amine | C18H21NO4 | 详情 | 详情 | |
| (IV) | 41394 | N-(3,4-dimethoxybenzyl)(3,4-dimethoxyphenyl)methanamine; N,N-bis(3,4-dimethoxybenzyl)amine | C18H23NO4 | 详情 | 详情 | |
| (V) | 36173 | 2,4,6,8-tetrachloropyrimido[5,4-d]pyrimidine | C6Cl4N4 | 详情 | 详情 | |
| (VI) | 41395 | N-[8-[bis(3,4-dimethoxybenzyl)amino]-2,6-dichloropyrimido[5,4-d]pyrimidin-4-yl]-N,N-bis(3,4-dimethoxybenzyl)amine; 2,6-dichloro-N(4),N(4),N(8),N(8)-tetrakis(3,4-dimethoxybenzyl)pyrimido[5,4-d]pyrimidine-4,8-diamine | C42H44Cl2N6O8 | 详情 | 详情 | |
| (VII) | 41397 | 1-amino-2-propanol | 78-96-6 | C3H9NO | 详情 | 详情 |
| (VIII) | 41396 | 1-([4,8-bis[bis(3,4-dimethoxybenzyl)amino]-6-[(2-hydroxypropyl)amino]pyrimido[5,4-d]pyrimidin-2-yl]amino)-2-propanol | C48H60N8O10 | 详情 | 详情 |