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【结 构 式】 
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【药物名称】 【化学名称】5-[5-(10H-Phenothiazin-10-ylmethyl)-1,3,4-thiadiazol-2-ylaminomethyl]-2-thioxoperhydropyrimidine-4,6-dione 【CA登记号】 【 分 子 式 】C20H16N6O2S3 【 分 子 量 】468.58152 |
【开发单位】Chaudhary Charan Singh University (Originator), Lala Lajpat Rai Memorial Med Col (Originator) 【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS |
合成路线1
Alkylation of phenothiazine (I) by ethyl chloroacetate (II) in the presence of K2CO3 affords the ester (III). Subsequent condensation of (III) with thiosemicarbazide (IV) gives the acyl thiosemicarbazide (V), which is cyclized to the thiadiazole derivative (VI) in concentrated H2SO4. Finally, Mannich condensation of aminothiadiazole (VI) with thiobarbituric acid (VII) and formaldehyde furnishes the desired compound.
| 【1】 Archana; Rani, P.; Bajaj, K.; Srivastava, V.K.; Chandra, R.; Kumar, A.; Synthesis of newer indolyl/phenothiazinyl substituted 2-oxo/thiobarbituric acid derivatives as potent anticonvulsant agents. Arzneim-Forsch Drug Res 2003, 53, 5, 301. |
| 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) | 57751 | 10H-Phenothiazine; 2,3,5,6-Dibenzo-1,4-thiazine; Dibenzo-1.4-thiazine; Dibenzothiazine; Phenothiazine; Thiodiphenylamine | 92-84-2 | C12H9NS | 详情 | 详情 |
| (II) | 16601 | ethyl chloroacetate; ethyl 2-chloroacetate | 105-39-5 | C4H7ClO2 | 详情 | 详情 |
| (III) | 64835 | ethyl 2-(10H-phenothiazin-10-yl)acetate | C16H15NO2S | 详情 | 详情 | |
| (IV) | 12954 | 1-Hydrazinecarbothioamide; Thiosemicarbazide | 79-19-6 | CH5N3S | 详情 | 详情 |
| (V) | 64836 | 2-[2-(10H-phenothiazin-10-yl)acetyl]-1-hydrazinecarbothioamide | C15H14N4OS2 | 详情 | 详情 | |
| (VI) | 64837 | 5-(10H-phenothiazin-10-ylmethyl)-1,3,4-thiadiazol-2-amine; 5-(10H-phenothiazin-10-ylmethyl)-1,3,4-thiadiazol-2-ylamine | C15H12N4S2 | 详情 | 详情 | |
| (VII) | 64838 | 2-thioxodihydro-4,6(1H,5H)-pyrimidinedione | C4H4N2O2S | 详情 | 详情 |