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【结 构 式】 
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【药物名称】Naringenin 【化学名称】(-)-5,7-Dihydroxy-2(S)-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one 【CA登记号】480-41-1 【 分 子 式 】C15H12O5 【 分 子 量 】272.25989 |
【开发单位】 【药理作用】Atherosclerosis Therapy, CARDIOVASCULAR DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Cell Adhesion Inhibitors |
合成路线1
The condensation of phloroglucinol (I) with 4-methoxycarbonyloxy)cinnamoyl chloride (II) by means AlCl3 in hot nitrobenzene gives 4'-O-methoxycarbonylnaringenin (III), which is hydrolyzed with NH3 in water-acetone.
| 【1】 Rosenmund, M.; Rosenmund, K.W.; Uber die synthese des naringenins und phloretins. Ber 1928, 61, 2608-13. |
| 【2】 Castaner, J.; Serradell, M.N.; Aboul-Enein, H.Y.; Naringenin. Drugs Fut 1984, 9, 9, 653-654. |
合成路线2
The condensation of 2,4,6-trihydroxyacetophenone (IV) with tetraacetylbromoglucose (V) by means of NaOH in acetone-water gives tetraacetylphloracetophenone-4-O-glucoside (VI), which is condensed with 4-hydroxybenzaldehyde (VII), by means of KOH in alcohol yielding the chalcone derivative (VIII). Finally, this compound is cyclized and deprotected by a treatment with refluxing aqueous HCl.
| 【1】 Zemplen, G.; Bognar, R.; Synthese eines phloracetophenon-glucosids, eines naringenin-glucosids und des p-phlorhizins. Ber 1942, 75, 645-655. |
| 【2】 Castaner, J.; Serradell, M.N.; Aboul-Enein, H.Y.; Naringenin. Drugs Fut 1984, 9, 9, 653-654. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 34293 | 1-(2,4,6-trihydroxyphenyl)-1-ethanone | 480-66-0 | C8H8O4 | 详情 | 详情 |
| (V) | 27260 | (2R,3R,4S,5S,6R)-4,5-bis(acetoxy)-6-[(acetoxy)methyl]-2-bromotetrahydro-2H-pyran-3-yl acetate | 572-09-8 | C14H19BrO9 | 详情 | 详情 |
| (VI) | 34294 | (2R,3R,4S,5R)-6-(4-acetyl-3,5-dihydroxyphenoxy)-4,5-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-2H-pyran-3-yl acetate | C22H26O13 | 详情 | 详情 | |
| (VII) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (VIII) | 34295 | (E)-1-(2,6-dihydroxy-4-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one | C21H22O10 | 详情 | 详情 |