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【结 构 式】 
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【药物名称】MM-36 【化学名称】5-(Anthracen-9ylmethylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile hydrochloride 【CA登记号】 【 分 子 式 】C31H35ClN2O2 【 分 子 量 】503.0898 |
【开发单位】Università degli Studi di Bologna (Originator), Università degli Studi di Firenze (Originator) 【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS |
合成路线1
Reaction of 2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile (I) with 1,3-dibromopropane (II) in the presence of n-butyllithium at -78 C provided bromonitrile (III). Alkylation of potassium phthalimide (V) with 9-(chloromethyl)anthracene (IV) yielded the N-alkylated phthalimide (VI), and subsequent hydrazinolysis gave the aminomethyl compound (VIII). Finally, amine (VIII) was alkylated with bromide (III) in Et3N at 60 C to produce the title compound, which was isolated as the corresponding hydrochloride salt.
| 【1】 Teodori, E.; Dei, S.; Quidu, P.; et al.; Design, synthesis, and in vitro activity of catamphiphilic reverters of multidrug resistance: Discovery of a selective, highly efficacious chemosensitizer with potency in the nanomolar range. J Med Chem 1999, 42, 10, 1687. |
| 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) | 30391 | 2-(3,4-dimethoxyphenyl)-3-methylbutanenitrile; alpha-Isopropylveratryl cyanide | 20850-49-1 | C13H17NO2 | 详情 | 详情 |
| (II) | 12581 | 1,3-Dibromopropane | 109-64-8 | C3H6Br2 | 详情 | 详情 |
| (III) | 30392 | 5-bromo-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile | C16H22BrNO2 | 详情 | 详情 | |
| (IV) | 30393 | 9-(chloromethyl)anthracene | 24463-19-2 | C15H11Cl | 详情 | 详情 |
| (V) | 27890 | Potassium phthalimide | 1074-82-4 | C8H4KNO2 | 详情 | 详情 |
| (VI) | 30394 | 2-(9-anthrylmethyl)-1H-isoindole-1,3(2H)-dione | C23H15NO2 | 详情 | 详情 | |
| (VII) | 30395 | 9-anthrylmethanamine; 9-anthrylmethylamine | 2476-68-8 | C15H13N | 详情 | 详情 |