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【结 构 式】 
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【药物名称】Palmitoyl cytarabine, Palmitoyl Ara-C 【化学名称】N4-Palmitoyl-1-beta-D-arabinofuranosylcytosine 【CA登记号】55726-45-9 【 分 子 式 】C25H43N3O6 【 分 子 量 】481.63796 |
【开发单位】Asahi Kasei (Originator) 【药理作用】ONCOLYTIC DRUGS, Antimetabolites |
合成路线1
This compound can be obtained in two different ways: 1) By condensation of 1-beta-D-arabinofuranosylcytosine (I) with palmitic anhydride (II) in hot dioxane. 2) By acylation of cytidine (III) with palmitic anhydride (II) in hot dioxane to yield N4-palmitoylcytidine (IV), which is then isomerized by treatment with POCl3 in ethyl acetate.
| 【1】 Ishida, T.; et al.; JP 7626884 . |
| 【2】 Ishida, T.; et al.; JP 7707974 . |
| 【3】 Ishida, T.; et al.; JP 7632573 . |
| 【4】 Akiyama, M.; et al.; The synthesis of new derivatives of 1-beta-D-arabinofuranosylcytosine. Chem Pharm Bull 1978, 26, 3, 981-984. |
| 【5】 Ishida, T.; et al.; JP 7648679 . |
| 【6】 Ishida, T.; et al. (Asahi Chemical Industry Co., Ltd.); N4-Acylarabinonucleosides. DE 2461862 . |
| 【7】 Ishida, T.; et al. (Asahi Chemical Industry Co., Ltd.); N4-Acylarabinonucleosides and the preparation thereof. DE 2426304 . |
| 【8】 Cabanillas, F.; Castaner, J.; Palmitoyl/Stearoyl Ara-C. Drugs Fut 1980, 5, 12, 617. |
| 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) | 32709 | Cytarabine; Cytosine Beta-D-Arabinofuranoside; 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone | 147-94-4 | C9H13N3O5 | 详情 | 详情 |
| (II) | 39214 | acetic hexadecanoic anhydride | C18H34O3 | 详情 | 详情 | |
| (III) | 27920 | Cytidine; 4-amino-1-((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone | 65-46-3 | C9H13N3O5 | 详情 | 详情 |
| (IV) | 27921 | N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2-oxo-1,2-dihydro-4-pyrimidinyl]hexadecanamide | C25H43N3O6 | 详情 | 详情 |
Extended Information