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【结 构 式】 
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【分子编号】32672 【品名】9-chloroacridine 【CA登记号】1207-69-8 |
【 分 子 式 】C13H8ClN 【 分 子 量 】213.66596 【元素组成】C 73.08% H 3.77% Cl 16.59% N 6.56% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 4-nitro-m-anisidine (I) with methanesulfonyl chloride in pyridine gives 4-nitromethanesulfony-m-anisidine (II), which is reduced with Fe and aqueous HCl yielding 4-aminomethanesulfony-m-anisidine (III) . Finally, this compound is condensed with 9-chloroacridine (IV).
| 【1】 Denny, W.A.; et al.; Potential antitumor agents. 26. Anionic congeners of the 9-anilinoacridine. J Med Chem 1977, 21, 1, 5-10. |
| 【2】 Cain, B.F.; et al.; Potential antitumor agents. 16. 4-(Acridin-9-ylamino)methanesulfonanilides. J Med Chem 1975, 18, 11, 1110-17. |
| 【3】 Cain, B.F.; et al.; Potential antitumor agents. 23. 4'-(9-Acridinylamino)alkanesulfonanilide congeners bearing hydrophilic functionality. J Med Chem 1977, 20, 8, 987-996. |
| 【4】 Paton, D.M.; Blancafort, P.; Serradell, M.N.; Castaner, J.; m-AMSA. Drugs Fut 1980, 5, 6, 277. |
| 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) | 32670 | 3-methoxy-4-nitroaniline; 3-methoxy-4-nitrophenylamine | C7H8N2O3 | 详情 | 详情 | |
| (II) | 32671 | N-(3-methoxy-4-nitrophenyl)methanesulfonamide | C8H10N2O5S | 详情 | 详情 | |
| (III) | 30496 | N-(4-amino-3-methoxyphenyl)methanesulfonamide | C8H12N2O3S | 详情 | 详情 | |
| (IV) | 32672 | 9-chloroacridine | 1207-69-8 | C13H8ClN | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)The condensation of 2-nitroimidazole (I) with N-(3-bromopropyl)phthalimide (II) by means of NaH in DMSO gives N-[3-(2-nitroimidazol-1-yl)propyl]phthalimide (III), which is treated with hydrazine in ethanol/water to yield 3-(2-nitroimidazol-1-yl)propylamine (IV). Finally this amine is condensed with 9-chloroacridine by means of TEA.
| 【1】 Bloomer, W.D.; Papadopoulou, M.V.; Nitroheterocyclic-linked acridines as DNA-targeting bioreductive agents. Drugs Fut 1993, 18, 3, 231. |
| 【2】 DeCarneri, I.; Giraldi, P.N.; Mariotti, V.; Studies on antiprotozoans. Synthesis and biological activity of some styrylimidazole derivatives. J Med Chem 1968, 11, 60-70. |
| 【3】 Adams, G.E.; Ahmed, I.; Stratford, I.J. (Gerald Edward Adams; Ian James Stratford; Israr Ahmed); Bis(nitro-1-imidazolyl alkylamine) platinum complexes useful in radiotheraphy or chemotherapy. GB 2131020 . |
| 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) | 10145 | 2-Nitro-1H-imidazole; 2-Nitroimidazole | 527-73-1 | C3H3N3O2 | 详情 | 详情 |
| (II) | 15216 | N-(3-Bromopropyl)phthalimide; 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione | 5460-29-7 | C11H10BrNO2 | 详情 | 详情 |
| (III) | 41281 | 2-[3-(2-nitro-1H-imidazol-1-yl)propyl]-1H-isoindole-1,3(2H)-dione | C14H12N4O4 | 详情 | 详情 | |
| (IV) | 41282 | 3-(2-nitro-1H-imidazol-1-yl)-1-propanamine; 3-(2-nitro-1H-imidazol-1-yl)propylamine | C6H10N4O2 | 详情 | 详情 | |
| (V) | 32672 | 9-chloroacridine | 1207-69-8 | C13H8ClN | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(V)The condensation of 2-nitroimidazole (I) with N-(2-bromoethyl)phthalimide (II) by means of NaH in DMSO gives N-[2-(2-nitroimidazol-1-yl)ethyl]phthalimide (III), which is treated with hydrazine in ethanol/water to yield 2-(2-nitroimidazol-1-yl)ethylamine (IV). Finally this amine is condensed with 9-chloroacridine by means of TEA.
| 【1】 Bloomer, W.D.; Papadopoulou, M.V.; Nitroheterocyclic-linked acridines as DNA-targeting bioreductive agents. Drugs Fut 1993, 18, 3, 231. |
| 【2】 DeCarneri, I.; Giraldi, P.N.; Mariotti, V.; Studies on antiprotozoans. Synthesis and biological activity of some styrylimidazole derivatives. J Med Chem 1968, 11, 60-70. |
| 【3】 Adams, G.E.; Ahmed, I.; Stratford, I.J. (Gerald Edward Adams; Ian James Stratford; Israr Ahmed); Bis(nitro-1-imidazolyl alkylamine) platinum complexes useful in radiotheraphy or chemotherapy. GB 2131020 . |
| 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) | 10145 | 2-Nitro-1H-imidazole; 2-Nitroimidazole | 527-73-1 | C3H3N3O2 | 详情 | 详情 |
| (II) | 37025 | 2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione | 574-98-1 | C10H8BrNO2 | 详情 | 详情 |
| (III) | 41283 | 2-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione | C13H10N4O4 | 详情 | 详情 | |
| (IV) | 41284 | 2-(2-nitro-1H-imidazol-1-yl)ethylamine; 2-(2-nitro-1H-imidazol-1-yl)-1-ethanamine | C5H8N4O2 | 详情 | 详情 | |
| (V) | 32672 | 9-chloroacridine | 1207-69-8 | C13H8ClN | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)Treatment of 9-chloroacridine (I) with NaN3 in aqueous acetone affords azidoacridine (II), which is submitted to a cycloaddition reaction with 5-chloro-1-pentynyl (III) to yield 9-(triazol-1-yl)acridine (IV). Finally, (IV) is cyclized by thermolysis in hot diphenyl ether.
| 【1】 Ward, W.; Stanslas, J.; Hagan, D.J.; Ellis, M.J.; Stevens, M.F.G.; Turner, C.; Carmichael, J.; Hammonds, T.R.; Antitumor polycyclic acridines.7. Synthesis and biological properties of DNA affinic tetra- and pentacyclic acridines. J Med Chem 2000, 43, 8, 1563. |