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【结 构 式】 
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【分子编号】10147 【品名】1-Chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol 【CA登记号】 |
【 分 子 式 】C6H8ClN3O3 【 分 子 量 】205.60064 【元素组成】C 35.05% H 3.92% Cl 17.24% N 20.44% O 23.35% |
合成路线1
该中间体在本合成路线中的序号：(III),(V)[2H]-Labeled RSU-1069 is synthesized as follows: The condensation of 2-nitroimidazole (I) with 3-chloro-1,2-epoxypropane (II) gives 1-(3-chloro-2-hydroxypropyl)-2-nitroimidazole (III), which is oxidized with CrO3 - H2SO4 in acetone yielding 1-(3-chloro-2-oxopropyl)-2-nitroimidazole (IV). The reduction of (IV) with NaB[2H]4 in ethanol affords 1-(3-chloro-2-hydroxy-2(2H)-propyl)-2-nitroimidazole (V), which is cyclized with NaOH to the corresponding labeled epoxide (VI). Finally, this compound is condensed with aziridine (VII) by means of triethylamine in refluxing ethanol.
| 【1】 Webb, P.; Threadgill, M.D.; Labelled compounds of interest as antitumour agents. Part II (1). Synthesis of 2H and 3H isotopomers of RSU 1069 and Ro 03-8799 (pimonidazole). J Label Compd Radiopharm 1990, 28, 3, 257. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III),(V) | 10147 | 1-Chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol | C6H8ClN3O3 | 详情 | 详情 | |
| (I) | 10145 | 2-Nitro-1H-imidazole; 2-Nitroimidazole | 527-73-1 | C3H3N3O2 | 详情 | 详情 |
| (II) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (IV) | 10148 | 1-Chloro-3-(2-nitro-1H-imidazol-1-yl)acetone | C6H6ClN3O3 | 详情 | 详情 | |
| (V) | 44588 | 1-chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol | C6H8ClN3O3 | 详情 | 详情 | |
| (VI) | 10150 | 2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole | C6H7N3O3 | 详情 | 详情 | |
| (VI) | 44589 | 2-nitro-1-(2-oxiranylmethyl)-1H-imidazole | C6H7N3O3 | 详情 | 详情 | |
| (VII) | 10151 | Ethyleneimine; Aziridine; Azirane | 151-56-4 | C2H5N | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III),(V)[2H]-Labeled pimonidazole is synthesized as follows: The condensation of 2-nitroimidazole (I) with 3-chloro-1,2-epoxypropane (II) gives 1-(3-chloro-2-hydroxypropyl)-2-nitroimidazole (III), which is oxidized with CrO3 - H2SO4 in acetone yielding 1-(3-chloro-2-oxopropyl)-2-nitroimidazole (IV). The reduction of (IV) with NaB[2H]4 in ethanol affords 1-(3-chloro-2-hydroxy-2(2H)-propyl)-2-nitroimidazole (V), which is cyclized with NaOH to the corresponding labeled epoxide (VI). Finally, this compound is condensed with piperidine (VII) in refluxing ethanol.
| 【1】 Webb, P.; Threadgill, M.D.; Labelled compounds of interest as antitumour agents. Part II (1). Synthesis of 2H and 3H isotopomers of RSU 1069 and Ro 03-8799 (pimonidazole). J Label Compd Radiopharm 1990, 28, 3, 257. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III),(V) | 10147 | 1-Chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol | C6H8ClN3O3 | 详情 | 详情 | |
| (I) | 10145 | 2-Nitro-1H-imidazole; 2-Nitroimidazole | 527-73-1 | C3H3N3O2 | 详情 | 详情 |
| (II) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (IV) | 10148 | 1-Chloro-3-(2-nitro-1H-imidazol-1-yl)acetone | C6H6ClN3O3 | 详情 | 详情 | |
| (V) | 44588 | 1-chloro-3-(2-nitro-1H-imidazol-1-yl)-2-propanol | C6H8ClN3O3 | 详情 | 详情 | |
| (VI) | 10150 | 2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole | C6H7N3O3 | 详情 | 详情 | |
| (VI) | 44589 | 2-nitro-1-(2-oxiranylmethyl)-1H-imidazole | C6H7N3O3 | 详情 | 详情 | |
| (VII) | 10158 | Piperidine | 110-89-4 | C5H11N | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(III)2) By condensation of 1-(3-chloro 2 hydroxypropyl)-2-nitroimidazole (III) with piperidine (IV) in refluxing methanol.
| 【1】 Fisnerova, L.; Nemecek, O.; Method of producing 2-phenyl-2-carboxyethyl ester of 1-p-chlorobenzoyl-5-methoxy-2-methyl-3-indolyl acetic acid. CS 194284 . |
| 【2】 Castaner, J.; Prous, J.; RO-038799. Drugs Fut 1986, 11, 7, 580. |