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【结 构 式】 
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【药物名称】Atrimustine, Busramustine, Bestrabucil, KM-2210, Kregan 【化学名称】(17beta)-Estra-1,3,5(10)-triene-3,17-diol 3-benzoate 17-[[4-[4-[bis(2-chloroethyl)amino]phenyl]-1-oxobutoxy]acetate] 【CA登记号】75219-46-4 【 分 子 式 】C41H47Cl2NO6 【 分 子 量 】720.74084 |
【开发单位】Kureha (Originator) 【药理作用】ONCOLYTIC DRUGS, DNA-Damaging Drugs |
合成路线1
The benzoylation of 1,3,5(10)-estratrien-3,17beta-diol (I) with benzoyl chloride (II) by means of NaOH in THF-water gives 3-benzoyloxy-1,3,5(10)-estratrien-17beta-ol (III), which is acylated with bromoacetyl bromide (IV) by means of pyridine in THF-CCl4 yielding 3-benzoyloxy-17beta-bromoacetoxy 1,3,5(10)-estratriene (V). Finally, this compound is condensed with silver 4-[4-[bis(2-chloroethyl)amino]phenyl]butyrate (VI) in DMSO.
| 【1】 Asano, K.; Tamura, H.; Tanaka, H.; Enomoto, S.; Novel estradiol compound, its preparation and anti-tumor agent containing the same. BE 0878186; JP 55027121 . |
| 【2】 Castaner, J.; Serradell, M.N.; KM-2210. Drugs Fut 1984, 9, 5, 334. |
| 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) | 34210 | (8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | 50-28-2 | C18H24O2 | 详情 | 详情 |
| (II) | 10643 | (1S,2S,3R,4S,7S,8S,10R,13S)-10-(acetoxy)-1,7-bis(benzyloxy)-13-[[tert-butyl(dimethyl)silyl]oxy]-8,12,15,15-tetramethyl-5,9-dioxo-4-[(phenylsulfanyl)methyl]tricyclo[9.3.1.0(3,8)]pentadec-11-en-2-yl benzoate | C55H66O9SSi | 详情 | 详情 | |
| (III) | 34211 | (8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate | C25H28O3 | 详情 | 详情 | |
| (IV) | 14005 | 2-Bromoacetyl bromide; Bromoacetyl bromide | 598-21-0 | C2H2Br2O | 详情 | 详情 |
| (V) | 34212 | (8R,9S,13S,14S,17S)-17-[(2-bromoacetyl)oxy]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate | C27H29BrO4 | 详情 | 详情 | |
| (VI) | 34213 | silver(1+) 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate | C14H18AgCl2NO2 | 详情 | 详情 |