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【结 构 式】 
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【分子编号】25782 【品名】6-chloro-1,3-dimethoxy-7-nitro-9(10H)-acridinone 【CA登记号】 |
【 分 子 式 】C15H11ClN2O5 【 分 子 量 】334.71552 【元素组成】C 53.83% H 3.31% Cl 10.59% N 8.37% O 23.9% |
合成路线1
该中间体在本合成路线中的序号：(IV)Ullman reaction of 2,4-dichloro-5-nitrobenzoic acid (I) with 3,5-dimethoxyaniline (II) in the presence of cupric acetate gave the diphenylamine carboxylic acid (III), which was cyclized with polyphosphoric acid at 110 C to afford acridone (IV). This was N-alkylated with 2-(diethylamino)ethyl chloride in the presence of 18-crown-6 to provide (V). The nitro group of (V) was then reduced to amine (VI) using SnCl2 and HCl. Finally, O-demethylation with boiling 48% HBr yielded the target monodemethylated compound along with the dihydroxyl analogue, which were separated by chromatography.
| 【1】 Fravolini, A.; Tabarrini, O.; Sissi, C.; Sabatini, S.; Nocentini, G.; Barzi, A.; Cecchetti, V.; Miao, H.; Design and synthesis of modified quinolones as antitumoral acridones1. J Med Chem 1999, 42, 12, 2136. |
| 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) | 25779 | 2,4-dichloro-5-nitrobenzoic acid | C7H3Cl2NO4 | 详情 | 详情 | |
| (II) | 25780 | 3,5-dimethoxyaniline; 3,5-dimethoxyphenylamine | 10272-07-8 | C8H11NO2 | 详情 | 详情 |
| (III) | 25781 | 4-chloro-2-(3,5-dimethoxyanilino)-5-nitrobenzoic acid | C15H13ClN2O6 | 详情 | 详情 | |
| (IV) | 25782 | 6-chloro-1,3-dimethoxy-7-nitro-9(10H)-acridinone | C15H11ClN2O5 | 详情 | 详情 | |
| (V) | 25783 | 6-chloro-10-[2-(diethylamino)ethyl]-1,3-dimethoxy-7-nitro-9(10H)-acridinone | C21H24ClN3O5 | 详情 | 详情 | |
| (VI) | 25784 | 7-amino-6-chloro-10-[2-(diethylamino)ethyl]-1,3-dimethoxy-9(10H)-acridinone | C21H26ClN3O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)Ullman reaction of 2,4-dichloro-5-nitrobenzoic acid (I) with 3,5-dimethoxyaniline (II) in the presence of cupric acetate gave the diphenylamine carboxylic acid (III), which was cyclized with polyphosphoric acid at 110 C to afford acridone (IV). This was N-alkylated with 2-(diethylamino)ethyl chloride in the presence of 18-crown-6 to provide (V). The nitro group of (V) was then reduced to amine (VI) using SnCl2 and HCl. Finally, O-demethylation with boiling 48% HBr yielded the target dihydroxy compound along with the monodemethylated analogue, which were separated by chromatography.
| 【1】 Fravolini, A.; Tabarrini, O.; Sissi, C.; Sabatini, S.; Nocentini, G.; Barzi, A.; Cecchetti, V.; Miao, H.; Design and synthesis of modified quinolones as antitumoral acridones1. J Med Chem 1999, 42, 12, 2136. |
| 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) | 25779 | 2,4-dichloro-5-nitrobenzoic acid | C7H3Cl2NO4 | 详情 | 详情 | |
| (II) | 25780 | 3,5-dimethoxyaniline; 3,5-dimethoxyphenylamine | 10272-07-8 | C8H11NO2 | 详情 | 详情 |
| (III) | 25781 | 4-chloro-2-(3,5-dimethoxyanilino)-5-nitrobenzoic acid | C15H13ClN2O6 | 详情 | 详情 | |
| (IV) | 25782 | 6-chloro-1,3-dimethoxy-7-nitro-9(10H)-acridinone | C15H11ClN2O5 | 详情 | 详情 | |
| (V) | 25783 | 6-chloro-10-[2-(diethylamino)ethyl]-1,3-dimethoxy-7-nitro-9(10H)-acridinone | C21H24ClN3O5 | 详情 | 详情 | |
| (VI) | 25784 | 7-amino-6-chloro-10-[2-(diethylamino)ethyl]-1,3-dimethoxy-9(10H)-acridinone | C21H26ClN3O3 | 详情 | 详情 |