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【结 构 式】

【药物名称】YM-90K, YM-900(free base)

【化学名称】6-(1-Imidazolyl)-7-nitroquinoxaline-2,3-(1H,4H)-dione monohydrochloride

【CA登记号】154164-30-4, 143151-35-3 (free base), 157971-78-3 (YM-900)

【 分 子 式 】C11H8ClN5O4

【 分 子 量 】309.67051

【开发单位】Yamanouchi (Originator)

【药理作用】Antiepileptic Drugs, Cerebrovascular Diseases, Treatment of, Ischemic Stroke, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, AMPA Antagonists

合成路线1

The condensation of 5-chloro-2-nitroaniline (I) with imidazole (II) by means of KOH in DMSO gives 5-(1-imidazolyl)-2-nitroaniline (III). Hydrogenation of (III) over Pd/C in 1N HCl gives the diamine (IV), which is condensed with oxalic acid (V) in 4N HCl yielding 6-(1-imidazolyl)quinoxaline-2,3(1H,4H)-dione hydrochloride (VI). Finally, this compound is nitrated with HNO3/H2SO4.

1 Ngo, J.; Rabasseda, X.; Castaner, J.; YM-900. Drugs Fut 1997, 22, 3, 256.
2 Sakamoto, S.; Ohmori, J.; Shimizu-Sasamata, M.; et al.; Imidazolylquinoxaline-2,3-diones: Novel and potent antagonists of alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate (AMPA) excitatory amino acid receptor. 12th Int Symp Med Chem (Sept 13-17, Basel) 1992, Abst P-022.A..
3 Ohmori, J.; Sakamoto, S.; Kubota, H.; Shimizu-Sasamata, M.; Okada, M.; Kawasaki, S.; Hidaka, K.; Togami, J.; Furuya, T.; Murase, K.; 6-(1H-Imidazol-1-yl)-7-nitro-2,3(1H,4H)-quinoxalinedione hydrochloride (YM90K) and related compounds: Structure-activity relationships for the AMPA-type non-NMDA receptor. J Med Chem 1994, 37, 4, 467-75.
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) 15709 5-chloro-2-nitrophenylamine; 5-chloro-2-nitroaniline 1635-61-6 C6H5ClN2O2 详情 详情
(II) 10255 Imidazole; 1H-Imidazole 288-32-4 C3H4N2 详情 详情
(III) 15711 5-(1H-imidazol-1-yl)-2-nitroaniline; 5-(1H-imidazol-1-yl)-2-nitrophenylamine C9H8N4O2 详情 详情
(IV) 15712 4-(1H-imidazol-1-yl)-1,2-benzenediamine; 2-amino-4-(1H-imidazol-1-yl)phenylamine C9H10N4 详情 详情
(V) 15713 Oxalic acid 144-62-7 C2H2O4 详情 详情
(VI) 15714 6-(1H-imidazol-1-yl)-1,4-dihydro-2,3-quinoxalinedione hydrochloride C11H9ClN4O2 详情 详情
Extended Information