94001-59-9Relevant articles and documents
Novel and High Affinity 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues as Atypical Dopamine Transporter Inhibitors
Cao, Jianjing,Slack, Rachel D.,Bakare, Oluyomi M.,Burzynski, Caitlin,Rais, Rana,Slusher, Barbara S.,Kopajtic, Theresa,Bonifazi, Alessandro,Ellenberger, Michael P.,Yano, Hideaki,He, Yi,Bi, Guo-Hua,Xi, Zheng-Xiong,Loland, Claus J.,Newman, Amy Hauck
, p. 10676 - 10691 (2016/12/16)
The development of pharmacotherapeutic treatments of psychostimulant abuse has remained a challenge, despite significant efforts made toward relevant mechanistic targets, such as the dopamine transporter (DAT). The atypical DAT inhibitors have received attention due to their promising pharmacological profiles in animal models of cocaine and methamphetamine abuse. Herein, we report a series of modafinil analogues that have an atypical DAT inhibitor profile. We extended SAR by chemically manipulating the oxidation states of the sulfoxide and the amide functional groups, halogenating the phenyl rings, and/or functionalizing the terminal nitrogen with substituted piperazines, resulting in several novel leads such as 11b, which demonstrated high DAT affinity (Ki = 2.5 nM) and selectivity without producing concomitant locomotor stimulation in mice, as compared to cocaine. These results are consistent with an atypical DAT inhibitor profile and suggest that 11b may be a potential lead for development as a psychostimulant abuse medication.
Protic ionic liquids as recyclable solvents for the acid catalysed synthesis of diphenylmethyl thioethers
Henderson, Luke C.,Thornton, Megan T.,Byrne, Nolene,Fox, Bronwyn L.,Waugh, Kelsey D.,Squire, Jennifer S.,Servinis, Linden,Delaney, Joshua P.,Brozinski, Hannah L.,Andrighetto, Luke M.,Altimari, Jarrad M.
, p. 634 - 639 (2013/08/15)
The acid catalysed formation of diphenylmethyl (DPM) thioethers was successfully achieved using the protic ionic liquid (pIL) triethylamine: methanesulfonic acid (TeaMs) as the reaction solvent under microwave irradiation. A slight excess of methanesulfon
An efficient and chemoselective method for protection of thiols catalyzed by aluminumdodecatungstophosphate (AlPW12O40), as a highly water tolerant Lewis acid catalyst
Firouzabadi, Habib,Iranpoor, Nasser,Jafari, Abbas Ali
, p. 2683 - 2686 (2007/10/03)
Protection of various thiols with diphenylmethanol was achieved in high yields at room temperature using catalytic amounts of AlPW12O 40 in CH2Cl2. In the presence of this catalyst, protection of SH versus OH was achieved with high chemoselectivity and yields. The catalyst can be easily recovered and reused. Deprotection of DPM thioethers was also achieved using molecular iodine at reflux in CH2Cl 2 in high yields.
