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【结 构 式】 
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【药物名称】 【化学名称】(1R,3R)-1-(2,6-Difluorophenyl)-3-methyl-3H-1,3-thiazolo[3,4-a]benzimidazole 【CA登记号】 【 分 子 式 】C16H12F2N2S 【 分 子 量 】302.34824 |
【开发单位】Katholieke Universiteit Leuven (Originator), Università degli Studi di Messina (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY |
合成路线1
The cyclization of a mixture of phenylene-1,2-diamine (I), 2-sulfanylpropionic acid (II) and 2,6-difluorobenzaldehyde (III) in refluxing benzene gives a mixture of the two diastereomers of 1-(2,6-difluorophenyl)-3-methyl-1H,3H-thiazolo[3,4-a]benzimidazole, from which the trans-(racemic)-(IV) isomer has been isolated by silica gel column chromatography. The enantiomeric resolution has been performed by chiral HPLC affording the (1R, 3R)-(IV) isomer, the target compound.
| 【1】 Chimirri, A.; Grasso, S.; Monforte, A.M.; Monforte, P.; Rao, A.; Zappala, M.; Bruno, G.; Nicolo, F.; Pannecouque, C.; Witvrouw, M.; De Clercq, E.; Synthesis, structure and in vitro anti-human immunodeficiency virus activity of novel 3-methyl-1H,3H-thiazolo[3,4-a]benzimidazoles. Antivir Chem Chemother 1998, 9, 5, 431. |
| 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) | 12824 | 2-Aminophenylamine; o-Phenylenediamine; 1,2-Benzenediamine | 95-54-5 | C6H8N2 | 详情 | 详情 |
| (II) | 24361 | 2-sulfanylpropionic acid; 2-mercaptopropionic acid | 57965-30-7 | C3H6O2S | 详情 | 详情 |
| (III) | 25504 | 2,6-difluorobenzaldehyde | 637-55-8 | C7H4F2O | 详情 | 详情 |
| (IV) | 25505 | (1R,3R)-1-(2,6-difluorophenyl)-3-methyl-3H-[1,3]thiazolo[3,4-a]benzimidazole | C16H12F2N2S | 详情 | 详情 |