Exploration of novel chemical space: synthesis and in vitro evaluation of N-functionalized tertiary sulfonimidamides

Izzo, Flavia; Schäfer, Martina; Lienau, Philip; Ganzer, Ursula; Stockman, Robert; Lücking, Ulrich

Abstract

An unprecedented set of structurally diverse sulfonimidamides (47 compounds) has been prepared by various N‐functionalization reactions of tertiary =NH sulfonimidamide 2 aa. These N‐functionalization reactions of model compound 2 aa include arylation, alkylation, trifluoromethylation, cyanation, sulfonylation, alkoxycarbonylation (carbamate formation) and aminocarbonylation (urea formation). Small molecule X‐ray analyses of selected N‐functionalized products are reported. To gain further insight into the properties of sulfonimidamides relevant to medicinal chemistry, a variety of structurally diverse reaction products were tested in selected in vitro assays. The described N‐functionalization reactions provide a short and efficient approach to structurally diverse sulfonimidamides which have been the subject of recent, growing interest in the life sciences.

Citation

Izzo, F., Schäfer, M., Lienau, P., Ganzer, U., Stockman, R., & Lücking, U. (2018). Exploration of novel chemical space: synthesis and in vitro evaluation of N-functionalized tertiary sulfonimidamides. Chemistry - A European Journal, 24(37), 9295-9304. https://doi.org/10.1002/chem.201801557

• Journal Article Type: Article
• Acceptance Date: May 4, 2018
• Online Publication Date: May 4, 2018
• Publication Date: Jul 2, 2018
• Deposit Date: Mar 13, 2019
• Publicly Available Date: Mar 14, 2019
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 24
• Issue: 37
• Pages: 9295-9304
• DOI: https://doi.org/10.1002/chem.201801557
• Public URL: https://nottingham-repository.worktribe.com/output/1636941
• Publisher URL: https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201801557
• Contract Date: Mar 14, 2019