Cao Jianjing, Prisinzano Thomas E, Okunola Oluyomi M, Kopajtic Theresa, Shook Matthew, Katz Jonathan L, Newman Amy Hauck
Medicinal Chemistry, National Institute on Drug Abuse - Intramural Research Program, National Institutes of Health, 333 Cassell Drive, Baltimore, MD 21224.
ACS Med Chem Lett. 2010 Oct 10;2(1):48-52. doi: 10.1021/ml1002025.
A series of modafinil (1) analogues was synthesized wherein 1) para-halo-substitutents were added to the aryl rings, 2) the sulfoxide function was removed, and 3) the primary amide group was replaced with secondary and tertiary amides and amines to investigate the effects of these chemical modifications on DAT, SERT and NET binding. In addition, the locomotor-stimulant effects in mice of (±)-modafinil (1), its R- and S-enantiomers and its para-chloro sulfinylacetamide analogue (5c) were compared to those of cocaine.
合成了一系列莫达非尼（1）类似物，其中：1）在芳环上添加对卤代取代基；2）去除亚砜官能团；3）将伯酰胺基团替换为仲酰胺、叔酰胺和胺，以研究这些化学修饰对多巴胺转运体（DAT）、5-羟色胺转运体（SERT）和去甲肾上腺素转运体（NET）结合的影响。此外，还比较了（±）-莫达非尼（1）、其R-和S-对映体及其对氯亚磺酰乙酰胺类似物（5c）在小鼠体内的运动刺激作用与可卡因的作用。
