【结 构 式】 |
【分子编号】42947 【品名】6-amino-8,11-bis(benzyloxy)-7H-benzo[e]perimidin-7-one 【CA登记号】 |
【 分 子 式 】C29H21N3O3 【 分 子 量 】459.50416 【元素组成】C 75.8% H 4.61% N 9.14% O 10.45% |
合成路线1
该中间体在本合成路线中的序号:(II)The cyclization of anthracenedione derivative (I) with formamide in refluxing dimethylacetamide (DMA) in the presence of NH4VO3 affords benzo[e]perimidinone derivative (II), whose benzyl groups are removed with TFA to yield (III). Intermediate (III) is finally heated with 2-(dimethylamino)ethylamine (IV) in N,N,N',N'-tetramethylethylenediamine and a small amount of water. Alternatively, the target product can be obtained as follows: Reduction of the nitro group of anthracenedione derivative (V) by means of hydrazine and Pd/C provides amine (VI), which is then cyclized with formamide in phenol to give (VII). The removal of the benzyl groups of (VII) by treatment with TFA yields intermediate (VIII), which is finally condensed with 2-(dimethylamino)ethylamine (IV) under similar conditions as described for (III).
【1】 Stefanska, B.; Bontemps-Gracz, M.M.; Dzieduszycka, M.; Borowski, E.; 8,11-Dihydroxy-6-[8aminoalkyl)amino]-7H-benzo[e]perimidin-7-ones with activity in multidrug-resistant cell lines: Synthesis and antitumor evaluation. J Med Chem 1999, 42, 18, 3494. |
【2】 Borowski, E. (Politechnika Gdanska); New derivs. of 6-[(aminoalkyl)amino]-7H-benzo[e]-perimidin-7-one, method of their preparation, and their use as a medicament. WO 9825910 . |
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) | 42946 | 1,4-diamino-5,8-bis(benzyloxy)anthra-9,10-quinone | C28H22N2O4 | 详情 | 详情 | |
(II) | 42947 | 6-amino-8,11-bis(benzyloxy)-7H-benzo[e]perimidin-7-one | C29H21N3O3 | 详情 | 详情 | |
(III) | 42948 | 6-amino-8,11-dihydroxy-7H-benzo[e]perimidin-7-one | C15H9N3O3 | 详情 | 详情 | |
(IV) | 14881 | N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine | 108-00-9 | C4H12N2 | 详情 | 详情 |
(V) | 42949 | 1,4-bis(benzyloxy)-5-hydroxy-8-nitroanthra-9,10-quinone | C28H19NO7 | 详情 | 详情 | |
(VI) | 42950 | 1-amino-5,8-bis(benzyloxy)-4-hydroxyanthra-9,10-quinone | C28H21NO5 | 详情 | 详情 | |
(VII) | 42951 | 8,11-bis(benzyloxy)-6-hydroxy-7H-benzo[e]perimidin-7-one | C29H20N2O4 | 详情 | 详情 | |
(VIII) | 42952 | 6,8,11-trihydroxy-7H-benzo[e]perimidin-7-one | C15H8N2O4 | 详情 | 详情 |