Abstract
The crystal structure of 8-((dimethylamino)methyl)-1-(3-(dimethylamino)propyl)-1,7,8,9-tetrahydrochromeno[5,6-d]imidazol-2-amine (1), an inhibitor of the hepatitis C virus internal ribosome entry site, is described and compared to the structure of the compound in complex with the viral RNA target. Compound 1 crystallized by pentane vapor diffusion into dichloroethane solution. It crystallized in the monoclinic system, P21/c space group with unit cell parameters a = 15.7950(5) Å, b = 14.0128(4) Å, c = 8.8147(3) Å, β = 94.357(2)° and a cell volume of 1945.34(11) A−3. Packing interactions in the small molecule crystal lattice correspond to key interactions of the compound with the viral RNA target.
Graphical Abstract
The crystal structure of the title compound is described free and in complex with its viral target.
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References
Parsons J, Castaldi MP, Dutta S, Dibrov SM, Wyles DL, Hermann T (2009) Nature Chem Biol 5:823–825
Dibrov SM, Ding K, Brunn ND, Parker MA, Bergdahl BM, Wyles DL, Hermann T (2012) Proc Nat Acad Sci USA 109(14):5223–5228
Parker MA, Satkiewicz E, Hermann T, Bergdahl BM (2011) Molecules 16:281–290
Bruker (2005) SAINT. Bruker AXS, Madison, Wisconsin
Bruker (2001) SADABS: v.2.01, an empirical absorption correction program. Bruker AXS, Madison
Sheldrick GM (1997) SHELX-97, Program for crystal structure refinement. University of Gottingen, Germany
Acknowledgments
This work was supported in part by the National Institutes of Health, Grant No. AI72012. Support of the NMR facility by the National Science Foundation is acknowledged (CRIF Grant CHE-0741968).
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Dibrov, S.M., Parker, M.A., Bergdahl, B.M. et al. Crystal Structure of a Benzimidazole Hepatitis C Virus Inhibitor Free and in Complex with the Viral RNA Target. J Chem Crystallogr 43, 235–239 (2013). https://doi.org/10.1007/s10870-013-0410-5
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DOI: https://doi.org/10.1007/s10870-013-0410-5