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【结 构 式】

【分子编号】44589

【品名】2-nitro-1-(2-oxiranylmethyl)-1H-imidazole

【CA登记号】

【 分 子 式 】C6H7N3O3

【 分 子 量 】169.14

【元素组成】C 42.61% H 4.17% N 24.84% O 28.38%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

[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:(VI)

[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
Extended Information