Scholz, M.S.M.S.ScholzWingen, L.M.L.M.WingenBrunst, S.S.BrunstWittmann, S.K.S.K.WittmannCardoso, I.L.A.I.L.A.CardosoWeizel, L.L.WeizelProschak, E.E.Proschak2022-03-062022-03-062020https://publica.fraunhofer.de/handle/publica/26695110.1016/j.ejmech.2019.111766In the present article we describe the creation of a small carboranylcarboxamide compound library followed by a screening campaign at the soluble epoxide hydrolase (sEH). We identified meta-carboranyl alkylamides, -anilides, and -benzylamides as potent sEH inhibitors. Furthermore, we optimized the scaffolds and we derived structure-activity relationships. The most potent benzylamide 33 (MS1) was similar to a previously reported adamantane derivative and gave an IC50 value of 0.07 mM for meta- and 0.08 mM for para-carborane at isolated sEH. The ortho-derivative suffered deboronation. The results underline the potential of carboranes as non-natural 3-D pharmacophores to extend the chemical space in drug discovery.en540571572journal article