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【结 构 式】 
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【药物名称】SB-RA-131012 【化学名称】[2aR-(2aα,4β,4aβ,6β,9α,10β,11β,12α,12aα,12bα)]- 6,9,12b-Triacetoxy-12-benzoyloxy-4-[3-(4-benzoylphenyl)- 2(E)-propenoyloxy]-10,11-(carbonyldioxy)- 4a,8,13,13-tetramethyl-2a,3,4,4a,5,6,10,11,12,12a,12bdodecahydro- 1H-7,11-methanocyclododeca[3,4]benz- [1,2-b]oxet-5-one 【CA登记号】 【 分 子 式 】C50H48O16 【 分 子 量 】904.93046 |
【开发单位】State Univ. New York at Stony Brook, Stony Brook, NY (US); Roswell Park Cancer Inst., Buffalo, NY (US) 【药理作用】ONCOLYTIC DRUGS, RESISTANCE MODIFIERS |
合成路线1
Palladium-catalyzed coupling of 4-bromobenzophenone (I) with methyl acrylate (II) afforded 4-benzoylcinnamic ester (III), which was hydrolyzed to acid (IV) with NaOH. Condensation with taxane derivative (V) in the presence of DCC and DMAP then provided the target ester.
| 【1】 Bernacki, R.J.; Ojima, I. (State University of New York, Albany); Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compsns. thereof. EP 0966456; US 5811452; WO 9830553 . |
| 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) | 18447 | (4-bromophenyl)(phenyl)methanone | 90-90-4 | C13H9BrO | 详情 | 详情 |
| (II) | 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 |
| (III) | 18449 | methyl (E)-3-(4-benzoylphenyl)-2-propenoate | C17H14O3 | 详情 | 详情 | |
| (IV) | 18450 | (E)-3-(4-benzoylphenyl)-2-propenoic acid | C16H12O3 | 详情 | 详情 | |
| (V) | 18451 | (1S,2S,4S,7R,9S,10S,12R,15R,16S)-4,12,15-tris(acetoxy)-9-hydroxy-10,14,20,20-tetramethyl-11,18-dioxo-6,17,19-trioxapentacyclo[11.6.1.0(1,16).0(3,10).0(4,7)]icos-13-en-2-yl benzoate | C34H38O14 | 详情 | 详情 |