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【结 构 式】 
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【药物名称】Suramin sodium, NF-060, CI-1003, NSC-34936, Germanin, Moranyl, Antrypol, Metaret 【化学名称】8,8'-[Ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di(1,3,5-naphthalenetrisulfonic acid) hexasodium salt 【CA登记号】129-46-4, 145-63-1 (free acid) 【 分 子 式 】C51H34N6Na6O23S6 【 分 子 量 】1429.18883 |
【开发单位】Bayer (Originator), National Cancer Institute (Originator), Pfizer (Licensee) 【药理作用】ANTIINFECTIVE THERAPY, Antitrypanosomals, Oncolytic Drugs, Prostate Cancer Therapy, Treatment of Helminthic Diseases, Treatment of Protozoal Diseases, Heparanase Inhibitors |
合成路线1
Several procedures for obtaining titte compound have been reported: In one method the acylation of 1 naphthylamine 4,6,8-trisulfonic acid trisodium salt (I) with 4 methyl-3-nitrobenzoyt chloride (II) yields the correspond ing amide (III), which is reduced with Fe in acetic acid to the amine (IV). Acylation of (IV) with 3-nitrobenzoyl chloride (V) affords the nitro diamide (VI), which is reduced with Fe and acetic acid before to the amine (VII). Finally, this compound is condensed with phosgene.
| 【1】 Heymann; Angew Chem 1924, 37, 585. |
| 【2】 Freres, P.; Foruneau, E.; Trefouel, J.; The manufacture of a symmetrical urea of m-aminobenzoyl-m-aminomethylbenzoyl-1-napthylamino-4,6,8-trisulphonate of sodium. GB 224849 . |
| 【3】 Fourneau; et al.; Compt Rend Acad Sci 1924, 178, 675. |
| 【4】 Castaner, J.; Serradell, M.N.; Suramin Sodium. Drugs Fut 1986, 11, 10, 860. |
| 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) | 23913 | 8-Aminonaphthalene-1,3,5-trisulfonic acid trisodium salt | C10H6NNa3O9S3 | 详情 | 详情 | |
| (II) | 23914 | 4-methyl-3-nitrobenzoyl chloride | 10397-30-5 | C8H6ClNO3 | 详情 | 详情 |
| (III) | 23915 | 4-Methyl-3-nitro-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt | C18H11N2Na3O12S3 | 详情 | 详情 | |
| (IV) | 23916 | 3-Amino-4-methyl-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt | C18H13N2Na3O10S3 | 详情 | 详情 | |
| (V) | 15293 | 3-nitrobenzoyl chloride; m-nitrobenzoyl chloride | 121-90-4 | C7H4ClNO3 | 详情 | 详情 |
| (VI) | 23918 | 4-Methyl-3-(3-nitrobenzamido)-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt | C25H16N3Na3O13S3 | 详情 | 详情 | |
| (VII) | 23919 | 3-(3-Aminobenzamido)-4-methyl-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt | C25H18N3Na3O11S3 | 详情 | 详情 |