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An Efficient New Route to Dihydropyranobenzimidazole Inhibitors of HCV Replication
Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA 92182, USA
Department of Chemistry and Biochemistry, University of California, La Jolla, San Diego, CA 92093, USA
* Authors to whom correspondence should be addressed.
Received: 15 November 2010; in revised form: 24 December 2010 / Accepted: 28 December 2010 / Published: 30 December 2010
Abstract: A class of dihydropyranobenzimidazole inhibitors was recently discovered that acts against the hepatitis C virus (HCV) in a new way, binding to the IRES-IIa subdomain of the highly conserved 5' untranslated region of the viral RNA and thus preventing the ribosome from initiating translation. However, the reported synthesis of these compounds is lengthy and low-yielding, the intermediates are troublesome to purify, and the route is poorly structured for the creation of libraries. We report a streamlined route to this class of inhibitors in which yields are far higher and most intermediates are crystalline. In addition, a key variable side chain is introduced late in the synthesis, allowing analogs to be easily synthesized for optimization of antiviral activity.
Keywords: HCV; benzimidazole; RNA; replication; inhibitor
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MDPI and ACS Style
Parker, M.A.; Satkiewicz, E.; Hermann, T.; Bergdahl, B.M. An Efficient New Route to Dihydropyranobenzimidazole Inhibitors of HCV Replication. Molecules 2011, 16, 281-290.
Parker MA, Satkiewicz E, Hermann T, Bergdahl BM. An Efficient New Route to Dihydropyranobenzimidazole Inhibitors of HCV Replication. Molecules. 2011; 16(1):281-290.
Parker, Matthew A.; Satkiewicz, Emily; Hermann, Thomas; Bergdahl, B. Mikael. 2011. "An Efficient New Route to Dihydropyranobenzimidazole Inhibitors of HCV Replication." Molecules 16, no. 1: 281-290.