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【结 构 式】 
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【药物名称】Aranoza, Aranose, CRC-0510375 【化学名称】3-(alpha-L-Arabinopyranosyl)-1-methyl-1-nitrosourea 【CA登记号】167396-23-8, 95342-54-4 (alpha-D-isomer), 103667-91-0 (undefined isomer) 【 分 子 式 】C7H13N3O6 【 分 子 量 】235.19816 |
【开发单位】Cancer Research Center RAMS (Originator) 【药理作用】Lung Cancer Therapy, Melanoma Therapy, Oncolytic Drugs, Small Cell Lung Cancer Therapy, DNA-Damaging Drugs, Nitrosoureas |
合成路线1
The synthesis of aranoza (IV) was accomplished by the condensation of N-methylurea (II) with L-arabinose (I), which yields 3-a-L-arabinopyranosyl-1-methylurea (III), followed by nitrosation of the latter. In slightly alkaline conditions or upon heating, aranoza undergoes intramolecular carbamoylation to produce N1O3-carbonyl-a-L-arabinopyranosylamine (V), gaseous N2 and methanol. It is important that diazomethane (CH2N2) is not formed under these conditions as demonstrated by gas chromatography and mass spectrometry.
| 【1】 Perevodchikova, N.I.; Gorbacheva, L.B.; Preobrazhenskaya, M.N.; Aranoza. Drugs Fut 2003, 28, 10, 941. |
| 【2】 Preobrazhenskaja, M.N.; Miniker, T.D.; Yartseva, I.V.; Kikot, B.S.; Nikitina, T.V.; Ignat'eva, E.V.; Pichugina, L.V.; Timofeeva, A.K.; Kenke, I.K.; Murkhanov, V.I.; Method of synthesis of 3-(1-alpha-L-arabinopyranozyl)-1-methyl-1-nitrosourea (aranose) - an antitumor preparation. SU 1711456 . |
| 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) | 16002 | alpha-L-arabinopyranose; Tetrahydro-2H-pyran-2,3,4,5-tetrol; L(+)-Arabinosa | 7296-56-2 | C5H10O5 | 详情 | 详情 |
| (II) | 16003 | N-methylurea; methyl-urea | 598-50-5 | C2H6N2O | 详情 | 详情 |
| (III) | 16004 | N-methyl-N'-[(2R,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]urea; N-methyl-N'-(3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)urea | C7H14N2O5 | 详情 | 详情 | |
| (V) | 16005 | (1S,5R,8S,9R)-8,9-dihydroxy-2,6-dioxa-4-azabicyclo[3.3.1]nonan-3-one; 1-methyl-2-oxo-N-(3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)-1-hydrazinecarboxamide | C6H9NO5 | 详情 | 详情 |