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【结 构 式】 
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【药物名称】NLA-2 【化学名称】N-[2-(2-Nitro-1H-imidazol-1-yl)ethyl]acridine-9-amine hydrochloride 【CA登记号】 【 分 子 式 】C18H16ClN5O2 【 分 子 量 】369.81352 |
【开发单位】Stanford University (Originator), University of Auckland (Originator), University of Pittsburgh (Originator) 【药理作用】ONCOLYTIC DRUGS, Radiation Therapy, Radiosensitizers |
合成路线1
The condensation of 2-nitroimidazole (I) with N-(2-bromoethyl)phthalimide (II) by means of NaH in DMSO gives N-[2-(2-nitroimidazol-1-yl)ethyl]phthalimide (III), which is treated with hydrazine in ethanol/water to yield 2-(2-nitroimidazol-1-yl)ethylamine (IV). Finally this amine is condensed with 9-chloroacridine by means of TEA.
| 【1】 Bloomer, W.D.; Papadopoulou, M.V.; Nitroheterocyclic-linked acridines as DNA-targeting bioreductive agents. Drugs Fut 1993, 18, 3, 231. |
| 【2】 DeCarneri, I.; Giraldi, P.N.; Mariotti, V.; Studies on antiprotozoans. Synthesis and biological activity of some styrylimidazole derivatives. J Med Chem 1968, 11, 60-70. |
| 【3】 Adams, G.E.; Ahmed, I.; Stratford, I.J. (Gerald Edward Adams; Ian James Stratford; Israr Ahmed); Bis(nitro-1-imidazolyl alkylamine) platinum complexes useful in radiotheraphy or chemotherapy. GB 2131020 . |
| 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) | 10145 | 2-Nitro-1H-imidazole; 2-Nitroimidazole | 527-73-1 | C3H3N3O2 | 详情 | 详情 |
| (II) | 37025 | 2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione | 574-98-1 | C10H8BrNO2 | 详情 | 详情 |
| (III) | 41283 | 2-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione | C13H10N4O4 | 详情 | 详情 | |
| (IV) | 41284 | 2-(2-nitro-1H-imidazol-1-yl)ethylamine; 2-(2-nitro-1H-imidazol-1-yl)-1-ethanamine | C5H8N4O2 | 详情 | 详情 | |
| (V) | 32672 | 9-chloroacridine | 1207-69-8 | C13H8ClN | 详情 | 详情 |
Extended Information