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【结 构 式】 
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【药物名称】C-75 【化学名称】4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid 【CA登记号】191282-49-2 (cis-isomer), 191282-48-1 (trans-isomer) 【 分 子 式 】C14H22O4 【 分 子 量 】254.32904 |
【开发单位】Johns Hopkins University (Originator), Fasgen (Licensee) 【药理作用】Antiobesity Drugs, METABOLIC DRUGS, ONCOLYTIC DRUGS, Treatment of Nutritional Disorders, Carnitine O-Palmitoyltransferase 1 (CPT-1) Activators, Fatty Acid Synthase Inhibitors |
合成路线1
p-Methoxybenzyl itaconate (III) was prepared by reaction of itaconic anhydride (I) with p-methoxybenzyl alcohol (II) at 55-60 C (1). Condensation of the lithium enolate of (III) with nonanal (IV) in THF at -78 C gave adduct (V), which upon treatment with trifluoroacetic acid underwent cyclization and benzyl ester deprotection to yield the corresponding butyrolactone as a diastereomeric mixture. The major trans isomer was finally isolated by flash chromatography.
| 【1】 Mani, N.S.; Li, J.N.; Frehywot, G.; Pizer, E.S.; Kuhajda, F.P.; Townsend, G.A.; Syntesis and antitumor activity of an inhibitor fatty acid synthase. Proceedings of the National Academy of Sciences of the United States of America 2000, 97, 7, 3450. |
| 【2】 Kuhajda, F.P.; Mani, N.S.; Pasternack, G.R.; Townsend, C.A. (Johns Hopkins University); Inhibition of fatty acid synthase as a means to reduce adipocyte mass. WO 9718806 . |
| 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) | 12891 | 3-Methylenedihydro-2,5-furandione; Itaconic anhydride | 2170-03-8 | C5H4O3 | 详情 | 详情 |
| (II) | 38861 | 4-Methoxybenzenemethanol; (4-methoxyphenyl)methanol; 4-Methoxybenzyl alcohol; Anis alcohol; Anisyl Alcohol; 4-Anisic Alcohol; p-Anisyl alcohol; Anise alcohol | 105-13-5 | C8H10O2 | 详情 | 详情 |
| (III) | 38862 | 2-[2-[(4-methoxybenzyl)oxy]-2-oxoethyl]acrylic acid | C13H14O5 | 详情 | 详情 | |
| (IV) | 38863 | nonanal | 124-19-6 | C9H18O | 详情 | 详情 |
| (V) | 38864 | 2-(2-hydroxy-1-[[(4-methoxybenzyl)oxy]carbonyl]decyl)acrylic acid | C22H32O6 | 详情 | 详情 |