6533b822fe1ef96bd127d7d0
RESEARCH PRODUCT
Methyl 4-[5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-imidazol-2-ylsulfanyl]butanoate
Stefan LauferDieter SchollmeyerPierre KochChristiane Bäuerleinsubject
CrystallographyQD901-999ChemistryHydrogen bondNucleophilic substitutionGeneral Materials ScienceGeneral ChemistryCrystal structureDihedral angleCondensed Matter PhysicsBioinformaticsOrganic PapersMedicinal chemistrydescription
The title compound, C19H18FN3O2S, was synthesized in the course of studies on 2-alkylsufanylimidazoles as p38 mitogen-activated protein kinase inhibitors. The synthesis was achieved by nucleophilic substitution of 4-(4-fluorophenyl)-5-(pyridin-4-yl)-1,3-dihydroimidazole-2-thione with methyl 4-bromobutanoate. The five-membered heterocycle makes dihedral angles of 32.4 (2) and 18.3 (2)° with the fluorophenyl and pyridinyl rings, respectively, indicating a low degree of conjugation between these rings. Intramolecular C—H...N and intermolecular N—H...N hydrogen bonds as well as C—H...π interactions seem to be effective in stabilization of the crystal structure.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-04-17 | Acta Crystallographica Section E Structure Reports Online |