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【结 构 式】 
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【分子编号】41075 【品名】N-(3-iodobenzyl)guanidine 【CA登记号】80663-95-2 |
【 分 子 式 】C8H10IN3 【 分 子 量 】275.09209 【元素组成】C 34.93% H 3.66% I 46.13% N 15.27% |
合成路线1
该中间体在本合成路线中的序号：(III)MIBG is synthesized as follows: A mixture of m-iodobenzylamine (I) hydrochloride and cyanamide (II) is stirred and heated at 100 C for 4h. The resulting m-iodobenzylguanidine is converted to the bicarbonate salt by treatment with aqueous potassium bicarbonate. Addition of dilute sulfuric acid gives the guanidine sulfate. To prepare the labeled compound, the unlabeled m-iodobenzylguanidinium sulfate is dissolved in water and treated with carrier-free Na[131]I. Refluxing for 72h and passage through Cellex D anion exchange cellulose gives [131]iodobenzylguanidine sulfate. Another more efficient method of carrying out the exchange-labeling step has been reported.
| 【1】 Eastland, G. Jr.; Iobenguane (131I). Drugs Fut 1989, 14, 5, 427. |
| 【2】 Wieland, D.M.; Wu, J.-L.; Brown, L.E.; Mengner, T.J.; Swanson, D.P.; Beierwaltes, W.H.; Radiolabeled adrenergic neuron-blocking agents: Adrenomedullary imaging with [131]iodobenzylguanidine. J Nucl Med 1980, 21, 349-53. |
| 【3】 Shapiro, B.; Copp, J.E.; Sisson, J.C.; Eyres, P.L.; Wallis, J.; Beierwaltes, W.H.; Iodine-131-m-iodobenzylguanidine for the locating of suspected pheochromocytoma: Experience in 400 cases. J Nucl Med 1985, 26, 576-85. |
合成路线2
该中间体在本合成路线中的序号：(X)
| 【1】 Zan LB, Yang YY, Liu NJ, et al. 2007. Synthesis of N-[[3-(trimethylsilyl) phenyl] methyl]guanidine as precursor for carrier-free [3-(iodo-125I) phenyl] guanidine. Yuanzineng Kexue Jishu, 4(6):689～693. |
| 【2】 Amarteya JK, A1-Jammaza I, Lambrecht RM. 2001. An efficient batch preparation of high specific activity [123I] and [124I] mIBG. Applied Radiation and Isotop, 54(5): 711～714. |
| 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) | 29096 | Chloro(trimethyl)silane; Trimethylsilyl chloride; Trimethylchlorosilane | 75-77-4 | C3H9ClSi | 详情 | 详情 |
| (II) | 67158 | 3-Bromotoluene;1-Bromo-3-methylbenzene | 591-17-3 | C7H7Br | 详情 | 详情 |
| (III) | 67159 | trimethyl(m-tolyl)silane | C10H16Si | 详情 | 详情 | |
| (IV) | 67160 | 1-bromopyrrolidine-2,5-dione | 128-08-5 | C4H4BrNO2 | 详情 | 详情 |
| (V) | 67161 | (3-(bromomethyl)phenyl)trimethylsilane | C10H15BrSi | 详情 | 详情 | |
| (VI) | 12376 | Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione | 85-41-6 | C8H5NO2 | 详情 | 详情 |
| (VII) | 67162 | 2-(3-(trimethylsilyl)benzyl)isoindoline-1,3-dione | C18H19NO2Si | 详情 | 详情 | |
| (VIII) | 67163 | (3-(trimethylsilyl)phenyl)methanamine | C10H17NSi | 详情 | 详情 | |
| (IX) | 67164 | 1-(3-(trimethylsilyl)benzyl)guanidine | C11H19N3Si | 详情 | 详情 | |
| (X) | 41075 | N-(3-iodobenzyl)guanidine | 80663-95-2 | C8H10IN3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(II)
| 【1】 Dougan H, Lyster DM, Vincent JS, et al. 1998. Kit type labeling of [123I]-metaiodobenzylguanidine. Journal of Labelled Compounds and Radiopharmacentical, 25(5): 531～544. |
| 【2】 Zan LB, Yang YY, Liu NJ, et al. 2007. Synthesis of N-[[3-(trimethylsilyl) phenyl] methyl]guanidine as precursor for carrier-free [3-(iodo-125I) phenyl] guanidine. Yuanzineng Kexue Jishu, 4(6):689～693. |