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【结 构 式】 
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【分子编号】21810 【品名】2-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic acid; 3-Carboxmethyl rhadanine; Rhodanine-N-acetic acid 【CA登记号】5718-83-2 |
【 分 子 式 】C5H5NO3S2 【 分 子 量 】191.23164 【元素组成】C 31.4% H 2.64% N 7.32% O 25.1% S 33.54% |
与该中间体有关的原料药合成路线共 2 条
合成路线1
该中间体在本合成路线中的序号：(II)By condensation of beta-methylcinnamylaldehyde (I) with 3-(carboxymethyl)rhodanine (II) by means of sodium acetate in refluxing acetic acid.
| 【1】 Hiroshi, T.; Tetsuya, M.; Takeshi, M.; Akio, A.; Masanori, K.; Fumio, H.; Tadao, T.; Masaki, H. (Ono Pharmaceutical Co., Ltd.); Rhodanine derivs., process for their preparation, . EP 0047109; US 4464382 . |
| 【2】 Castaner, J.; Prous, J.; Epalrestat. Drugs Fut 1987, 12, 4, 336. |
合成路线2
该中间体在本合成路线中的序号：(IV)1-Methoxynaphthalene (I) was lithiated with n-butyllithium and subsequently treated with N-methylformanilide (II) to give the 2-naphthaldehyde (III). The Knoevenagel condensation of (III) with the rhodanineacetic acid (IV) in the presence of NaOAc in AcOH provided the target 5-(alkylidene)thiazolidine.
| 【1】 Fresneau, P.; Cussac, M.; Morand, J.M.; Szymonski, B.; Tranqui, D.; Leclerc, G.; Synthesis, activity, and molecular modeling of new 2,4-dioxo-5-(naphthylmethylene)-3-thiazolidineacetic acids and 2-thioxo analogues as potent aldose reductase inhibitors. J Med Chem 1998, 41, 24, 4706. |
| 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) | 21807 | methyl 1-naphthyl ether; 1-methoxynaphthalene | 2216-69-5 | C11H10O | 详情 | 详情 |
| (II) | 20360 | methyl(phenyl)formamide;N-Methylformanilide;N-Formyl-N-methylaniline;Methylphenylformamide;N-methyl-N-phenylformamide;N-Methyl-N-formylaniline;N-Formyl-N-methylaniline | 93-61-8 | C8H9NO | 详情 | 详情 |
| (III) | 21809 | 1-methoxy-2-naphthaldehyde | C12H10O2 | 详情 | 详情 | |
| (IV) | 21810 | 2-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic acid; 3-Carboxmethyl rhadanine; Rhodanine-N-acetic acid | 5718-83-2 | C5H5NO3S2 | 详情 | 详情 |
Extended Information