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【结 构 式】 
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【分子编号】31633 【品名】2,2,2-trichloroethyl (11S,11aS)-8-[3-[(5-[[(5-[[(5-[[(5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)oxy]-3-o 【CA登记号】 |
【 分 子 式 】C46H51Cl3N12O12 【 分 子 量 】1070.34272 【元素组成】C 51.62% H 4.8% Cl 9.94% N 15.7% O 17.94% |
合成路线1
该中间体在本合成路线中的序号：(VI)The acylation of N-deformyldistamycin (I) with 4-formamido-1-methyl-1H-pyrrole-2-carboxylic acid (II) by means of carbonyldiimidazole (CDI) in DMF gives the tetrapyrrole (III), which is deformylated as usual to yield the aminotetrapyrrole (IV). The condensation of the pyrrolobenzodiazepin-8-yloxypropionic acid (V) with the tetrapyrrole derivative (IV) by means of EDC and DIEA in DMF gives the troc protected target molecule (III), which is finally treated with Cd/Pb in aqueous NH4OAc. The synthesis of the intermediate pyrrolobenzodiazepin-8-yloxypropionic acid (I) has already been described in scheme2700821a, corresponding to the synthesis of the compound with EN 270082.
| 【1】 D'Alessio, R.; et al.; Structure-activity relationship of novel distamycin a derivatives: Synthesis and antitumor activity. Bioorg Med Chem Lett 1994, 4, 12, 1467. |
| 【2】 Cacciari, B.; Baraldi, P.G.; Balboni, G.; et al.; Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c][1,4]benzodiazepine and minor-groove-binding oligopyrrole carriers. J Med Chem 1999, 42, 25, 5131. |
| 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) | 26888 | N-(3-amino-3-iminopropyl)-4-[[(4-[[(4-amino-1-methyl-1H-pyrrol-2-yl)carbonyl]amino]-1-methyl-1H-pyrrol-2-yl)carbonyl]amino]-1-methyl-1H-pyrrole-2-carboxamide | C21H27N9O3 | 详情 | 详情 | |
| (II) | 31630 | 4-(formylamino)-1-methyl-1H-pyrrole-2-carboxylic acid | C7H8N2O3 | 详情 | 详情 | |
| (III) | 31631 | N-(5-[[(5-[[(5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide | C28H33N11O5 | 详情 | 详情 | |
| (IV) | 31632 | N-(5-[[(5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)-4-[[(4-amino-1-methyl-1H-pyrrol-2-yl)carbonyl]amino]-1-methyl-1H-pyrrole-2-carboxamide | C27H33N11O4 | 详情 | 详情 | |
| (V) | 26887 | 3-([(11S,11aS)-11-hydroxy-7-methoxy-5-oxo-10-[(2,2,2-trichloroethoxy)carbonyl]-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl]oxy)propionic acid | C19H21Cl3N2O8 | 详情 | 详情 | |
| (VI) | 31633 | 2,2,2-trichloroethyl (11S,11aS)-8-[3-[(5-[[(5-[[(5-[[(5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl)oxy]-3-o | C46H51Cl3N12O12 | 详情 | 详情 |