【结 构 式】 |
【分子编号】54750 【品名】4-oxo-N-propyl-4-(2-thioxo-1,3-thiazolidin-3-yl)butanamide 【CA登记号】 |
【 分 子 式 】C10H16N2O2S2 【 分 子 量 】260.38132 【元素组成】C 46.13% H 6.19% N 10.76% O 12.29% S 24.63% |
合成路线1
该中间体在本合成路线中的序号:(IX)The reaction of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (I) with SOCl2, followed by dechlorination with Zn/HCl, gives 5-hydroxy-2-methyl-4H-pyran-4-one (II), which is condensed with formaldehyde to yield 3-hydroxy-2-(hydroxymethyl)-6-methyl-4H-pyran-4-one (III). The protection of the aromatic OH group of (III) with Bn-Br affords the benzyl ether (IV), which is treated with methylamine to provide the corresponding 4-pyridone (V). The reaction of the OH group of (V) with phthalimide (VI) by means of DEAD and PPh3 gives the expected phthalimido derivative (VII), which is cleaved with hydrazine to yield the aminomethyl derivative (VIII). The condensation of the amino group of (VIII) with the activated amide (IX) (obtained by condensation of N-propylsuccinamic acid (X) with 2-thiazolidinone (XI) by means of DCC and DMAP) affords the adduct (XII), which is finally debenzylated by hydrogenation with H2 over Pd/C to provide the target succinamide derivative.
【1】 Liu, Z.D.; et al.; Design, synthesis, and evaluation of novel 2-substituted 3-hydroxypyridin-4-ones: Structure-activity investigation of metalloenzyme inhibition by iron chelators. J Med Chem 2002, 45, 3, 631. |
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) | 13501 | Kojic acid; 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one | 501-30-4 | C6H6O4 | 详情 | 详情 |
(II) | 45934 | 5-hydroxy-2-methyl-4H-pyran-4-one | C6H6O3 | 详情 | 详情 | |
(III) | 48643 | 3-hydroxy-2-(hydroxymethyl)-6-methyl-4H-pyran-4-one | C7H8O4 | 详情 | 详情 | |
(IV) | 48644 | 3-(benzyloxy)-2-(hydroxymethyl)-6-methyl-4H-pyran-4-one | C14H14O4 | 详情 | 详情 | |
(V) | 54747 | 3-(benzyloxy)-2-(hydroxymethyl)-1,6-dimethyl-4(1H)-pyridinone | C15H17NO3 | 详情 | 详情 | |
(VI) | 12376 | Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione | 85-41-6 | C8H5NO2 | 详情 | 详情 |
(VII) | 54748 | 2-{[3-(benzyloxy)-1,6-dimethyl-4-oxo-1,4-dihydro-2-pyridinyl]methyl}-1H-isoindole-1,3(2H)-dione | C23H20N2O4 | 详情 | 详情 | |
(VIII) | 54749 | 2-(aminomethyl)-3-(benzyloxy)-1,6-dimethyl-4(1H)-pyridinone | C15H18N2O2 | 详情 | 详情 | |
(IX) | 54750 | 4-oxo-N-propyl-4-(2-thioxo-1,3-thiazolidin-3-yl)butanamide | C10H16N2O2S2 | 详情 | 详情 | |
(X) | 54752 | 4-oxo-4-(propylamino)butanoic acid | C7H13NO3 | 详情 | 详情 | |
(XI) | 54751 | Thiazolidine-2-thione | C3H5NS2 | 详情 | 详情 | |
(XII) | 54753 | N~1~-{[3-(benzyloxy)-1,6-dimethyl-4-oxo-1,4-dihydro-2-pyridinyl]methyl}-N~4~-propylsuccinamide | C22H29N3O4 | 详情 | 详情 |