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【结 构 式】 
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【药物名称】 【化学名称】2-[N-(Benzyloxycarbonyl)-L-leucyl-glycyl-L-prolyl]benzothiazole 【CA登记号】 【 分 子 式 】C28H32N4O5S 【 分 子 量 】536.65504 |
【开发单位】CNRS (Originator), Universidade de Brasilia (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antitrypanosomals, Treatment of Protozoal Diseases |
合成路线1
Condensation of the Weinreb amide of N-Boc-proline (I) with the lithium anion of benzothiazole (II) in THF at -78 C gave benzothiazolyl ketone (III), which was reduced with NaBH4 to afford the diastereomeric mixture of alcohols (IV). Deprotection of the Boc group of (IV) by means of HCl in EtOAc provided pyrrolidine (V). This was then coupled with Z-leucyl-glycine (VI) in the presence of PyBOP to give the peptidyl alcohol (VII). Finally, Swern oxidation of (VII) furnished the corresponding ketone.
| 【1】 Santana, J.; Gullet, C.; Schrével, J.; Frappier, F.; Maoulida, C.; Grellier, P.; Joyeau, R.; Teixeira, A.R.L.; Synthesis and activity of pyrrolidinyl- and thiazolidinyl-dipeptide derivatives as inhibitors of the Tc80 prolyl oligopeptidase from Trypanosoma cruzi. Eur J Med Chem 2000, 35, 2, 257. |
| 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) | 46320 | tert-butyl (2S)-2-[[methoxy(methyl)amino]carbonyl]-1-pyrrolidinecarboxylate | C12H22N2O4 | 详情 | 详情 | |
| (II) | 36784 | 1,3-benzothiazole | 95-16-9 | C7H5NS | 详情 | 详情 |
| (III) | 46321 | tert-butyl (2S)-2-(1,3-benzothiazol-2-ylcarbonyl)-1-pyrrolidinecarboxylate | C17H20N2O3S | 详情 | 详情 | |
| (IV) | 46322 | tert-butyl (2S)-2-[(R)-1,3-benzothiazol-2-yl(hydroxy)methyl]-1-pyrrolidinecarboxylate | C17H22N2O3S | 详情 | 详情 | |
| (V) | 46323 | (R)-1,3-benzothiazol-2-yl[(2S)pyrrolidinyl]methanol | C12H14N2OS | 详情 | 详情 | |
| (VI) | 46318 | 2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoyl)amino]acetic acid | C16H22N2O5 | 详情 | 详情 | |
| (VII) | 46324 | benzyl (1S)-1-[[(2-[(2S)-2-[(R)-1,3-benzothiazol-2-yl(hydroxy)methyl]pyrrolidinyl]-2-oxoethyl)amino]carbonyl]-3-methylbutylcarbamate | C28H34N4O5S | 详情 | 详情 |