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【结 构 式】 
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【药物名称】 【化学名称】8(S)-(Chloromethyl)-5-formyl-4-hydroxy-2-methyl-6-[3-(4-methoxyphenyl)-2(E)-propenoyl]-3,6,7,8-tetrahydrobenzo[1,2-b:4,3-b']dipyrrole-1-carboxylic acid methyl ester 【CA登记号】 【 分 子 式 】C25H23ClN2O6 【 分 子 量 】482.92486 |
【开发单位】Kyowa Hakko (Originator) 【药理作用】Oncolytic Drugs |
合成路线1
The segment-A moiety of duocarmycin analogue (I) was formylated with dichloromethyl methyl ether in the presence of TiCl4 to produce aldehyde (II). Opening of the cyclopropane ring of (II) by means of HCl in EtOAc gave rise to chloromethyl compound (III), which was subsequently coupled with 4-methoxycinnamic acid (IV) by means of EDC to furnish the title amide.
| 【1】 Okamoto, A.; Okabe, M.; Saito, H.; Amishiro, N.; Synthesis and antitumor activity of duocarmycin derivatives: Modification at the C-7 position of segement-A of A-ring pyrrole compounds. Bioorg Med Chem 2000, 8, 5, 1195. |
| 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) | 38365 | methyl (3bR,4aS)-2-methyl-8-oxo-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate | C14H14N2O3 | 详情 | 详情 | |
| (II) | 42106 | methyl (3bR,4aS)-7-formyl-2-methyl-8-oxo-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate | C15H14N2O4 | 详情 | 详情 | |
| (III) | 42107 | methyl (8S)-8-(chloromethyl)-5-formyl-4-hydroxy-2-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate | C15H15ClN2O4 | 详情 | 详情 | |
| (IV) | 42108 | (E)-3-(4-methoxyphenyl)-2-propenoic acid | 830-09-1 | C10H10O3 | 详情 | 详情 |
Extended Information