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【结 构 式】 
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【分子编号】31473 【品名】2,10-dihydroxy-6-methyl-12-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione 【CA登记号】 |
【 分 子 式 】C27H23N3O9 【 分 子 量 】533.49444 【元素组成】C 60.79% H 4.35% N 7.88% O 26.99% |
合成路线1
该中间体在本合成路线中的序号：(VII)The condensation of 6-(benzyloxy)indolylmagnesium bromide (I) with dihalomaleimide (II) afforded the diindolylmaleimide (III), which was oxidatively cyclized to produce indolocarbazole (IV). Glycosylation of (IV) with 1-chloro-tetrabenzylglucose (V) yielded the glycosyl derivative (VI). Subsequent deprotection of the benzyl ethers of (VI) by hydrogenolysis over Pd/C gave (VII). Conversion of the imide function of (VII) to anhydride (VIII) was then effected by treatment with KOH. Finally, coupling of (VIII) with hydrazine (IX) in DMF at 80 C yielded the title compound.
| 【1】 Ohkubo, M.; Nishimura, I.; Honma, T.; Nishimura, T.; Suda, H.; Morishima, H.; Arakawa, H.; Yoshinari, T.; Ito, S.; Nishimura, S.; Synthesis and biological activities of NB-506 analogues: Effects of the positions of two hydroxyl groups at the indole rings. Bioorg Med Chem Lett 1999, 9, 23, 3307. |
| 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) | 31467 | [6-(benzyloxy)-1H-indol-1-yl](bromo)magnesium | C15H12BrMgNO | 详情 | 详情 | |
| (II) | 31468 | 3,4-dibromo-1-methyl-1H-pyrrole-2,5-dione | C5H3Br2NO2 | 详情 | 详情 | |
| (III) | 31469 | 3,4-bis[6-(benzyloxy)-1H-indol-3-yl]-1-methyl-1H-pyrrole-2,5-dione | C35H27N3O4 | 详情 | 详情 | |
| (IV) | 31470 | 2,10-bis(benzyloxy)-6-methyl-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione | C35H25N3O4 | 详情 | 详情 | |
| (V) | 31471 | (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-6-chlorotetrahydro-2H-pyran; benzyl (2R,3S,4S,5R,6S)-3,5-bis(benzyloxy)-2-[(benzyloxy)methyl]-6-chlorotetrahydro-2H-pyran-4-yl ether | C34H35ClO5 | 详情 | 详情 | |
| (VI) | 31472 | 2,10-bis(benzyloxy)-6-methyl-12-[(2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl]-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione | C69H59N3O9 | 详情 | 详情 | |
| (VII) | 31473 | 2,10-dihydroxy-6-methyl-12-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione | C27H23N3O9 | 详情 | 详情 | |
| (VIII) | 31474 | 2,10-dihydroxy-12-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-12,13-dihydrofuro[3,4-c]indolo[2,3-a]carbazole-5,7-dione | C26H20N2O10 | 详情 | 详情 | |
| (IX) | 31434 | 2-hydrazino-1,3-propanediol | C3H10N2O2 | 详情 | 详情 |