【结 构 式】 |
【药物名称】 【化学名称】5-[2-[4-(1H-Imidazol-1-ylmethyl)phenoxy]ethoxy]-2,3-diphenylpyrazine 【CA登记号】 【 分 子 式 】C28H24N4O2 【 分 子 量 】448.52908 |
【开发单位】SSP (Originator) 【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Inducible Nitric Oxide Synthase (NOS-2) Inhibitors |
合成路线1
Alkylation of 5,6-diphenyl-2-pyrazinol (I) with mesylate derivative (II) furnishes the pyrazinyl ether (III). The aldehyde function of (III) is then reduced to alcohol (IV) employing NaBH4 in EtOH. Chlorination of alcohol (IV) by means of SOCl2 in the presence of catalytic DMF leads to the benzyl chloride (V). This is finally condensed with imidazole (VI) in hot DMF to yield the title compound
【1】 Konno, F.; Honda, H.; Ishii, F.; et al.; Novel anti-inflammatory agents with NO (nitric oxide) inhibition. 21st Symp Med Chem (Nov 28 2001, Kyoto) 2001, Abst 2P-24. |
【2】 Takeda, S.; Sato, S.; Takahashi, Y.; Nagao, Y.; Konno, F.; Ohtsuka, M.; Isomae, K.; Honda, H.; Hirota, H.; Kawamoto, N.; Ishii, F. (SSP Co., Ltd.); Imidazole derivs. or salts thereof and drugs containing the derivs. or the salts. EP 1295880; WO 0200648 . |
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) | 62497 | 5,6-diphenyl-2-pyrazinol | C16H12N2O | 详情 | 详情 | |
(II) | 62498 | 2-(4-formylphenoxy)ethyl methanesulfonate | C10H12O5S | 详情 | 详情 | |
(III) | 62499 | 4-{2-[(5,6-diphenyl-2-pyrazinyl)oxy]ethoxy}benzaldehyde | C25H20N2O3 | 详情 | 详情 | |
(IV) | 62500 | (4-{2-[(5,6-diphenyl-2-pyrazinyl)oxy]ethoxy}phenyl)methanol | C25H22N2O3 | 详情 | 详情 | |
(V) | 62501 | 5-{2-[4-(chloromethyl)phenoxy]ethoxy}-2,3-diphenylpyrazine; 2-[4-(chloromethyl)phenoxy]ethyl 5,6-diphenyl-2-pyrazinyl ether | C25H21ClN2O2 | 详情 | 详情 | |
(VI) | 10255 | Imidazole; 1H-Imidazole | 288-32-4 | C3H4N2 | 详情 | 详情 |
Extended Information