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【结 构 式】

【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
Extended Information