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【结 构 式】 
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【药物名称】BCX-1170 【化学名称】Furan-2-carboxylic acid 4-[3-amino-3-imino-1(E)-propenyl]phenyl ester methanesulfonate 【CA登记号】 【 分 子 式 】C15H16N2O6S 【 分 子 量 】352.36857 |
【开发单位】BioCryst (Originator) 【药理作用】Cardiovascular Diseases (Not Specified), CARDIOVASCULAR DRUGS, Complement Inhibitors, Serine Protease Inhibitors |
合成路线1
The reaction of 4-hydroxybenzaldehyde (I) with cyanacetic acid (II) by means of pyridine in toluene gives the 3-(4-hydroxyphenyl)propenenitrile (III), which by reaction first with methanolic HCl and then with methanolic ammonia is converted into the amidine (IV). Finally, this compound is condensed with 2-furylcarbonyl chloride (V) in pyridine and treated with methanesulfonic acid to afford the target sulfonate.
| 【1】 Niwas, S.; Moore, R.; Kilpatrick, J.M.; Babu, Y.S.; Johnson, H.; Kellogg, D.; Development of novel inhibitors of complement and coagulation serine proteases. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 088. |
| 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) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (II) | 12591 | Cyanoacetic Acid; 2-Cyanoacetic acid | 372-09-8 | C3H3NO2 | 详情 | 详情 |
| (III) | 27819 | (E)-3-(4-hydroxyphenyl)-2-propenenitrile | C9H7NO | 详情 | 详情 | |
| (IV) | 27820 | (E)-3-(4-hydroxyphenyl)-2-propenimidamide | C9H10N2O | 详情 | 详情 | |
| (V) | 26093 | 2-Furoyl chloride | 527-69-5 | C5H3ClO2 | 详情 | 详情 |
合成路线2
The acylation of (E)-3-(4-hydroxyphenyl)-2-propenamide (VI) with acetic anhydride gives the 4[(E)-3-amino-3-oxo-1-propenyl]phenyl acetate (VII), which by reaction first with BF3 ethearate and then with ammonia is converted into the amidine (IV). Finally, this compound is condensed with 2-furylcarbonyl chloride (V) in pyridine and treated with methanesulfonic acid to afford the target sulfonate.
| 【1】 Niwas, S.; Moore, R.; Kilpatrick, J.M.; Babu, Y.S.; Johnson, H.; Kellogg, D.; Development of novel inhibitors of complement and coagulation serine proteases. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 088. |