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【结 构 式】 
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【药物名称】SU-740(non-complexed), SU-840 【化学名称】4-tert-Butyl-2'-(carboxymethoxy)-4'-(3-methyl-2-butenyloxy)chalcone beta-cyclodextrin complex 【CA登记号】134336-72-4 (noncomplexed) 【 分 子 式 】C26H30O5 【 分 子 量 】422.526 |
【开发单位】Taisho (Originator) 【药理作用】Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS |
合成路线1
The synthesis of free compound is performed as follows: The condensation of 2-hydroxy-4-(3-methyl-2-butenyloxy)acetophenone (I) with 4-tert-butylbenzaldehyde (II) by means of KOH in hot ethanol gives 3-(4-tert-butylphenyl)-1-[4-hydroxy-4-(3-methyl-2-butenyloxy)phenyl]-2(E)-propen-1-one (III), which is condensed with ethyl bromoacetate (IV) by means of KOH in acetone to afford (E)-2-[2-(4-tert-butylcinnamoyl)-4-(3-methyl-2-butenyloxy)phenoxy] acetic acid ethyl ester (V). Finally, this compound is hydrolyzed with KOH in hot ethanol-water.
| 【1】 Yokomori, S.; Saijo, K.; Matsunaga, T.; Nakashima, Y.; Hatayama, K. (Taisho Pharmaceutical Co., Ltd.); Chalcone derivs. EP 0412803; JP 1991163042 . |
| 【2】 Yokomori, S.; Saijo, K.; Hatayama, M. (Taisho Pharmaceutical Co., Ltd.); Antiulcerative agents. JP 1993058885 . |
| 【3】 Rabasseda, X.; Castañer, J.; Mealy, N.; SU-840. Drugs Fut 1994, 19, 10, 923. |
| 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) | 16637 | 1-[2-hydroxy-4-[(3-methyl-2-butenyl)oxy]phenyl]-1-ethanone | C13H16O3 | 详情 | 详情 | |
| (II) | 16638 | 4-(tert-butyl)benzaldehyde; 4-tert-Butyl-benzaldehyde | 939-97-9 | C11H14O | 详情 | 详情 |
| (III) | 16639 | (E)-3-[4-(tert-butyl)phenyl]-1-[2-hydroxy-4-[(3-methyl-2-butenyl)oxy]phenyl]-2-propen-1-one | C24H28O3 | 详情 | 详情 | |
| (IV) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (V) | 16641 | ethyl 2-[2-[(E)-3-[4-(tert-butyl)phenyl]-2-propenoyl]-5-[(3-methyl-2-butenyl)oxy]phenoxy]acetate | C28H34O5 | 详情 | 详情 |