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【结 构 式】 
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【分子编号】51298 【品名】benzyl 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-pyrazole-3-carboxylate 【CA登记号】 |
【 分 子 式 】C34H37N11O6 【 分 子 量 】695.73832 【元素组成】C 58.7% H 5.36% N 22.15% O 13.8% |
合成路线1
该中间体在本合成路线中的序号：(V)The pyrazoledicarboxylic acid mono-methyl ester (I) was converted to the methyl benzyl diester (II) by treatment with benzyl bromide in the presence of DBU. Selective hydrolysis of the methyl ester function with KOH then provided the carboxylic acid (III). Coupling of acid (III) with deformyl distamycin A (IV) using EDC and HOBt gave amide (V). The protecting benzyl ester group of (V) was cleaved by catalytic hydrogenation over Pd/C to yield acid (VI). Amine (VIII) was obtained by acid cleavage of the Boc group from the protected precursor (VII). Subsequent coupling of amine (VIII) with carboxylic acid (VI) furnished the title compound.
| 【1】 Baraldi, P.G.; et al.; Design, synthesis, DNA binding, and biological evaluation of water-soluble hybrid molecules containing two pyrazole analogues of the alkylating cyclopropylpyrroloindole (CPI) subunit of the antitumor agent CC-1065 and polypyrrole minor groove binders. J Med Chem 2001, 44, 16, 2536. |
| 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) | 51295 | 5-(methoxycarbonyl)-1-methyl-1H-pyrazole-3-carboxylic acid | C7H8N2O4 | 详情 | 详情 | |
| (II) | 51296 | 3-benzyl 5-methyl 1-methyl-1H-pyrazole-3,5-dicarboxylate | C14H14N2O4 | 详情 | 详情 | |
| (III) | 51297 | 3-[(benzyloxy)carbonyl]-1-methyl-1H-pyrazole-5-carboxylic acid | C13H12N2O4 | 详情 | 详情 | |
| (IV) | 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 | |
| (V) | 51298 | benzyl 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-pyrazole-3-carboxylate | C34H37N11O6 | 详情 | 详情 | |
| (VI) | 51299 | 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-pyrazole-3-carboxylic acid | C27H31N11O6 | 详情 | 详情 | |
| (VII) | 51300 | tert-butyl 8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydropyrrolo[3,2-e]indazole-6(3H)-carboxylate | C16H20ClN3O3 | 详情 | 详情 | |
| (VIII) | 51301 | 8-(chloromethyl)-1-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indazol-4-ol | C11H12ClN3O | 详情 | 详情 |