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Crystal Structure of a Benzimidazole Hepatitis C Virus Inhibitor Free and in Complex with the Viral RNA Target

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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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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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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA

    Sergey M. Dibrov & Thomas Hermann

  2. Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA, 92182, USA

    Matthew A. Parker & B. Mikael Bergdahl

Authors
  1. Sergey M. Dibrov
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  2. Matthew A. Parker
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  3. B. Mikael Bergdahl
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  4. Thomas Hermann
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Corresponding author

Correspondence to Thomas Hermann.

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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

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