2-(9-anthrylmethyl)-1H-isoindole-1,3(2H)-dione -Drug Synthesis Database

【结构式】

【分子编号】30394

【品名】2-(9-anthrylmethyl)-1H-isoindole-1,3(2H)-dione

【CA登记号】

【分子式】C₂₃H₁₅NO₂

【分子量】337.37764

【元素组成】C 81.88% H 4.48% N 4.15% O 9.48%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

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.

参考文献中间体

合成目标

【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