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【结 构 式】

【药物名称】Dazmegrel, UK-38485

【化学名称】3-(1H-Imidazol-1-ylmethyl)-2-methyl-1H-indole-1-propanoic acid
      1-(2-Carboxyethyl)-2-methyl-3-(1H-imidazol-1-ylmethyl)indole

【CA登记号】76894-77-4

【 分 子 式 】C16H17N3O2

【 分 子 量 】283.33279

【开发单位】Pfizer (Originator)

【药理作用】Antiallergy/Antiasthmatic Drugs, Antiplatelet Therapy, Asthma Therapy, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, RESPIRATORY DRUGS, Prostanoid TP (Thromboxane A2) Antagonists, Thromboxane Synthase Inhibitors

合成路线1

The condensation of 2-methyl-3-(1H-imidazol-1-ylmethyl)indole (III) with acrylonitrile (IV) by means of benzyltrimethylammonium hydroxide (B) in dioxane gives 1-(2-cyanoethyl)-2-methyl-3-(1H-imidazol-1-ylmethyl)indole (V), which is then hydrolyzed with KOH in water. The reaction of compound (III) with methyl acrylate (VI) in the same conditions as before gives 1-(2-methoxy-carbonylethyl)-2-methyl-3-(1H-imidazol-1-ylmethyl)indole (VII), which is also hydrolyzed. Compound (III) can be obtained from 2-methylindole (I).

1 Cross, P.E.; Dickinson, R.P.; Randall, M.J.; Parry, M.J.; K-38485, a novel, selective thromboxane synthetase inhibitor with prolonged activity in vivo. N Am Med Chem Symp 1982, 68.
2 Cross, P.E.; Dickinson, R.P. (Pfizer Inc.); Inhibition of thromboxane synthetase by 3-(1-imidazolylalkyl)indoles. NL 8001351 .
3 Serradell, M.N.; Castaner, J.; Blancafort, P.; Grau, M.; UK-38485. Drugs Fut 1983, 8, 11, 947.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 10255 Imidazole; 1H-Imidazole 288-32-4 C3H4N2 详情 详情
(B) 36194 N,N,N-trimethyl(phenyl)methanaminium 4525-46-6 C10H16N 详情 详情
(I) 28747 2-methyl-1H-indole 95-20-5 C9H9N 详情 详情
(II) 36192 N,N-dimethyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine; N,N-dimethyl(2-methyl-1H-indol-3-yl)methanamine C12H16N2 详情 详情
(III) 36193 3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indole C13H13N3 详情 详情
(IV) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(V) 36195 3-[3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indol-1-yl]propanenitrile C16H16N4 详情 详情
(VI) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(VII) 36196 methyl 3-[3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indol-1-yl]propanoate C17H19N3O2 详情 详情
Extended Information