European Journal of Medicinal Chemistry p. 225 - 245 (2017)
Update date:2022-08-15
Topics:
Frings, Marcus
Bolm, Carsten
Blum, Andreas
Gnamm, Christian
Sulfoximines, sulfondiimides and sulfonimidamides are fascinating but not yet fully explored variants of the common sulfone or sulfonamide motif. In this study, we report the physicochemical and in vitro properties of sulfoximines and compare them with related analogs and isosteres. Furthermore, we present a matched molecular pair analysis of compounds from drug discovery projects within Boehringer Ingelheim. We demonstrate that the sulfoximine moiety is a chemically stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability. Moreover, their additional vectors at nitrogen enable simple chemical modifications and thus facilitate exploration and fine-tuning of the molecular properties. We conclude that sulfoximines and their congeners do not exhibit any intrinsic flaw but significantly enrich the toolbox of medicinal chemists.
View MoreDisynthesis Chemical Technology Co. Ltd.
Contact:+86-571-88194596
Address:Dengyun road 380, Gongshu district, Hangzhou city, China
SHANGHAI RORY FINE CHEMICALS CO.,LTD
Contact:0086-21-50702305/50343389
Address:Pudong Avenue 3040 building 2 room 103/50343389
Yantai Derun Liquid Crystal Materials Co. Ltd.
website:http://www.ytderun.com
Contact:86-535-6300169
Address:ROOM 90, XIANGFU STREET, FUSHAN NEW-HIGH-TECH IDUSTRY ZONE, YANTAI
Changzhou Medi-tech Bioscientific Co., Ltd.
Contact:86-519-83246372
Address:Number 115 Menghedadao Road, Changzhou, Jiangsu, China
Shanghai PotentPharm Science and Technology Co.,Ltd
Contact:86-021-51969655
Address:Unit B, Building 18, No.300, Chuantu Rd,Pudong District, Shanghai 201202, China
Doi:10.1002/hlca.19830660211
(1983)Doi:10.1016/S0031-9422(00)83738-3
(1986)Doi:10.1016/S0040-4039(03)00902-X
(2003)Doi:10.1021/jm00250a003
(1974)Doi:10.1016/S0040-4039(03)00848-7
(2003)Doi:10.1007/s13738-019-01711-5
(2019)