新产品编号:2091913
Chemical Name: 5-(2-Bromo-9H-fluoren-9-ylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile hydrochloride
项目整合开发状态: Biological Testing
项目研究机构: Universit?degli Studi di Bologna (Originator), Universit?degli Studi di Firenze (Originator), Universit?Paris Nord (Originator)
合成路线: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.
合成路线:Alkylation of the lithium salt of 2-(3,4-dimethoxyphenyl)isobutyronitrile (I) with 1,3-dibromopropane (II) gave the bromo nitrile (III).Conversion of bromide (III) into the desired primary amine (VI) was achieved through a Gabriel synthesis by condensation with potassium phthalimide (IV),followed by hydrazinolysis of the resultant N-substituted phthalimide (V).A two-step procedure was finally employed for the reductive alkylation of amine (VI),consisting of condensation between amine (VI) and the bromo fluorenone (VII) in the presence of titanium isopropoxide and then reduction of the intermediate (VIII) with NaBH3CN.
📌 参考资料/链接：
参考文献标题: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
文献作者:Teodori,E.; Dei,S.; Quidu,P.; Budriesi,R.; Chiarini,A.; Garnier-Suillerot,A.; Gualtieri,F.; Manetti,D.; Romanelli,M.N.; Scapecchi,S.
参考来源:J Med Chem 1999,42(10),1687
📄 详细内容
合成路线:Alkylation of the lithium salt of 2-(3,4-dimethoxyphenyl)isobutyronitrile (I) with 1,3-dibromopropane (II) gave the bromo nitrile (III).Conversion of bromide (III) into the desired primary amine (VI) was achieved through a Gabriel synthesis by condensation with potassium phthalimide (IV),followed by hydrazinolysis of the resultant N-substituted phthalimide (V).A two-step procedure was finally employed for the reductive alkylation of amine (VI),consisting of condensation between amine (VI) and the bromo fluorenone (VII) in the presence of titanium isopropoxide and then reduction of the intermediate (VIII) with NaBH3CN.
合成路线:The title amide is obtained by acylation of N,N-dimethyl-1,4-butanediamine (I) with 4-iodobenzoyl chloride (II) in the presence of Et3N in CH2Cl2.
参考文献标题:Structure-activity relationships and optimisation of the selective MDR modulator 2-(3,4-dimethoxyphenyl)-5-(9-fluorenylamino)-2-(methylethyl) pentanenitrile and its N-methyl derivative
文献作者:Dei,S.; Teodori,E.; Garnier-Suillerot,A.; Gualtieri,F.; Scapecchi,S.; Budriesi,R.; Chiarini,A.
参考来源:Bioorg Med Chem 2001,9(10),2673