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【结 构 式】 
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【药物名称】CT-5219 【化学名称】N-Acetyl-4-thia-D-prolyl-[4-O-(2,6-dichlorobenzyl)]-L-tyrosine 【CA登记号】217478-98-3 【 分 子 式 】C22H22Cl2N2O5S 【 分 子 量 】497.40104 |
【开发单位】Celltech (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Cell Adhesion Inhibitors, Integrin alpha4beta1 (VLA-4) Antagonists |
合成路线1
Coupling of N-acetyl-D-thioproline (I) with tyrosine methyl ester (II) using EDC and HOBt yielded dipeptide (III). Subsequent alkylation of the tyrosine phenolic group of (III) with 2,6-dichlorobenzyl bromide (IV) and NaH produced the dichlorobenzyl ether (V). The methyl ester group of (V) was finally hydrolyzed employing LiOH in aqueous THF.
| 【1】 Head, J.C.; Warrellow, G.J.; Archibald, S.C. (Celltech Chiroscience plc); Anti-inflammatory tyrosine derivs.. EP 0984981; US 6093696; WO 9854207 . |
| 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) | 40791 | (4S)-3-acetyl-1,3-thiazolidine-4-carboxylic acid | 24877-72-3 | C6H9NO3S | 详情 | 详情 |
| (II) | 21431 | methyl (2S)-2-amino-3-(4-hydroxyphenyl)propanoate | 1080-06-4 | C10H13NO3 | 详情 | 详情 |
| (III) | 40792 | methyl (2S)-2-([[(4S)-3-acetyl-1,3-thiazolidin-4-yl]carbonyl]amino)-3-(4-hydroxyphenyl)propanoate | C16H20N2O5S | 详情 | 详情 | |
| (IV) | 40793 | 2-(bromomethyl)-1,3-dichlorobenzene | 20443-98-5 | C7H5BrCl2 | 详情 | 详情 |
| (V) | 40794 | methyl (2S)-2-([[(4S)-3-acetyl-1,3-thiazolidin-4-yl]carbonyl]amino)-3-[4-[(2,6-dichlorobenzyl)oxy]phenyl]propanoate | C23H24Cl2N2O5S | 详情 | 详情 |
Extended Information