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【结 构 式】 
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【药物名称】 【化学名称】[5R-(5alpha,5abeta,8aalpha,9beta)]-9-(4-Amino-5-propyl-4H-1,2,4-triazol-3-ylsulfanyl)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 【CA登记号】165392-41-6 【 分 子 式 】C26H28N4O7S 【 分 子 量 】540.59966 |
【开发单位】Beijing Medical University (Originator), Lanzhou University (Originator) 【药理作用】Oncolytic Drugs, DNA-Intercalating Drugs, Epipodophyllotoxins |
合成路线1
Reaction of butyric acid hydrazide (I) with CS-2 and KOH gave dithiocarbamate (II), which was cyclized to aminotriazole (III) upon treatment with hydrazine. Demethylation of podophyllotoxin (IV) with HBr, followed by treatment with BaCO3 afforded 4'-demethyl epipodophyllotoxin (V). Finally, condensation of (V) with triazole (III) in the presence of trifluoroacetic acid furnished the title compound.
| 【1】 Chen, Y.Z.; Lu, K.K.; Synthesis and antitumor activities of 4beta-S-(5''-alkyl-4''-amino-1'',2'',4''-triazole-3''-yl)-4-deoxy-4'-O-demethyl-epipodophyllotoxin derivatives. Acta Pharm Sin 1999, 34, 1, 63. |
| 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) | 25210 | butanohydrazide | 3538-65-6 | C4H10N2O | 详情 | 详情 |
| (II) | 25211 | 2-butyryl-1-hydrazinecarbodithioate | C5H9N2OS2 | 详情 | 详情 | |
| (III) | 25212 | 1-amino-5-propyl-1H-pyrrol-2-ylhydrosulfide | C7H12N2S | 详情 | 详情 | |
| (IV) | 14608 | (5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one; Podophyllotoxin | 518-28-5 | C22H22O8 | 详情 | 详情 |
| (V) | 13053 | (5R,5aR,8aR,9S)-9-Hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one | 6559-91-7 | C21H20O8 | 详情 | 详情 |