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【结 构 式】 
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【分子编号】56050 【品名】2,4,6-tribromo-5-{[2-({4-[(4-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]amino}benzoyl)amino]benzoyl}amino)acetyl]amino}-N~1~,N~1~,N~3~,N~3~-tetrakis(2,3,4,5,6-pentahydroxyhexyl)isophthalamide 【CA登记号】 |
【 分 子 式 】C58H72Br3N7O28 【 分 子 量 】1554.95206 【元素组成】C 44.8% H 4.67% Br 15.42% N 6.31% O 28.81% |
合成路线1
该中间体在本合成路线中的序号：(XIV)Coupling between 4-nitrobenzoyl chloride (VI) and 4-aminobenzoic acid (VII) afforded nitrobenzamide (VIII), which was further reduced to amine (IX) by catalytic hydrogenation over Pd/C. Acylation of (IX) with phthalimidoacetyl chloride (X) yielded diamide (XI). The carboxyl group of (XI) was then activated as the corresponding acid chloride (XII) by treatment with SOCl2. Then, condensation of the glycylamide derivative (XIII) with acid chloride (XII) furnished amide (XIV).
| 【1】 Rousseaux, O.; Simonot, C. (Guerbet SA); Gadolinium complex tetramides and use in medical imaging. EP 1178975; FR 2793795; WO 0071526 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 18941 | p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride | 122-04-3 | C7H4ClNO3 | 详情 | 详情 |
| (VII) | 20004 | p-aminobenzoic acid; 4-aminobenzoic acid | 150-13-0 | C7H7NO2 | 详情 | 详情 |
| (VIII) | 56045 | 4-[(4-nitrobenzoyl)amino]benzoic acid | C14H10N2O5 | 详情 | 详情 | |
| (IX) | 56046 | 4-[(4-aminobenzoyl)amino]benzoic acid | C14H12N2O3 | 详情 | 详情 | |
| (X) | 10278 | 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl chloride | 6780-38-7 | C10H6ClNO3 | 详情 | 详情 |
| (XI) | 56047 | 4-[(4-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]amino}benzoyl)amino]benzoic acid | C24H17N3O6 | 详情 | 详情 | |
| (XII) | 56048 | 4-[(4-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]amino}benzoyl)amino]benzoyl chloride | C24H16ClN3O5 | 详情 | 详情 | |
| (XIII) | 56049 | 5-[(2-aminoacetyl)amino]-2,4,6-tribromo-N~1~,N~1~,N~3~,N~3~-tetrakis(2,3,4,5,6-pentahydroxyhexyl)isophthalamide | C34H57Br3N4O23 | 详情 | 详情 | |
| (XIV) | 56050 | 2,4,6-tribromo-5-{[2-({4-[(4-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]amino}benzoyl)amino]benzoyl}amino)acetyl]amino}-N~1~,N~1~,N~3~,N~3~-tetrakis(2,3,4,5,6-pentahydroxyhexyl)isophthalamide | C58H72Br3N7O28 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIV)Deprotection of the phthaloyl group of (XIV) by hydrazinolysis provided amine (XV). This was then coupled with the octaacid gadolinium chelate (V) in the presence of EDC and HOBt leading to the target amide.
| 【1】 Port, M.; et al.; P792: A rapid clearance blood pool agent for magnetic resonance imaging: Preliminary results. MAGMA Magn Reson Mater Phys Biol Med 2001, 12, 2-3, 121. |
| 【2】 Rousseaux, O.; Simonot, C. (Guerbet SA); Gadolinium complex tetramides and use in medical imaging. EP 1178975; FR 2793795; WO 0071526 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 56044 | gadolinium (2R)-2-{4,10-bis[(1R)-3-carboxy-1-carboxylatopropyl]-7-[(1R)-1-carboxy-4-hydroxy-4-oxobutyl]-1,4,7,10-tetraazacyclododecan-1-yl}-4-carboxybutanoate | C28H41GdN4O16 | 详情 | 详情 | |
| (XIV) | 56050 | 2,4,6-tribromo-5-{[2-({4-[(4-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]amino}benzoyl)amino]benzoyl}amino)acetyl]amino}-N~1~,N~1~,N~3~,N~3~-tetrakis(2,3,4,5,6-pentahydroxyhexyl)isophthalamide | C58H72Br3N7O28 | 详情 | 详情 | |
| (XV) | 56051 | 5-[(2-{[4-({4-[(2-aminoacetyl)amino]benzoyl}amino)benzoyl]amino}acetyl)amino]-2,4,6-tribromo-N~1~,N~1~,N~3~,N~3~-tetrakis(2,3,4,5,6-pentahydroxyhexyl)isophthalamide | C50H70Br3N7O26 | 详情 | 详情 |