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【结 构 式】 
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【药物名称】 【化学名称】1-(3,5-Diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol hydrochloride 【CA登记号】221659-13-8 【 分 子 式 】C17H18ClI2NO2 【 分 子 量 】557.60031 |
【开发单位】Molecular Design International (Originator) 【药理作用】Antidiabetic Drugs, Antiobesity Drugs, ENDOCRINE DRUGS, METABOLIC DRUGS, Treatment of Nutritional Disorders, Type 2 Diabetes Mellitus, Agents for, beta3-Adrenoceptor Agonists |
合成路线1
Acid chloride (II) was prepared by treatment of 3,5-diiodo-4-methoxyphenylacetic acid with oxalyl chloride (1). Coupling of (II) with amine (IV), obtained by reducing its nitro precursor (III) with LiAlH4, under Schotten-Baumann conditions furnished amide (V). Bischler-Napieralski cyclization of amide (V), followed by NaBH4 reduction of the intermediate dihydroisoquinoline yielded tetrahydroisoquinoline (VI). Finally, deprotection of the benzyl ether of (VI) by refluxing in the presence of HCl provided the title compound.
| 【1】 Shams, G.; Feller, D.R.; Zheng, W.; Konkar, A.A.; Miller, D.D.; Nikulin, V.I.; Vansal, S.S.; 2-Amino-4-benzyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridines: Novel selective beta3-adrenoceptor agonists. J Med Chem 1999, 42, 12, 2287. |
| 【2】 Feller, D.R.; Miller, D.D.; He, Y.; Vansal, S.S.; Nikulin, V.I.; Synthesis and human beta-adrenoceptor activity of 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol derivatives in vitro. J Med Chem 2000, 43, 4, 591. |
| 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) | 35234 | 2-(3,5-diiodo-4-methoxyphenyl)acetic acid | C9H8I2O3 | 详情 | 详情 | |
| (II) | 35235 | 2-(3,5-diiodo-4-methoxyphenyl)acetyl chloride | C9H7ClI2O2 | 详情 | 详情 | |
| (III) | 38829 | benzyl 3-[(E)-2-nitroethenyl]phenyl ether; 1-(benzyloxy)-3-[(E)-2-nitroethenyl]benzene | C15H13NO3 | 详情 | 详情 | |
| (IV) | 38830 | 3-(benzyloxy)phenethylamine; 2-[3-(benzyloxy)phenyl]-1-ethanamine | C15H17NO | 详情 | 详情 | |
| (V) | 38831 | N-[3-(benzyloxy)phenethyl]-2-(3,5-diiodo-4-methoxyphenyl)acetamide | C24H23I2NO3 | 详情 | 详情 | |
| (VI) | 38832 | 6-(benzyloxy)-1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline; benzyl 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydro-6-isoquinolinyl ether | C24H23I2NO2 | 详情 | 详情 |