Co-reporter:Hanmo Zhang, Kyu Ok Jeon, E. Ben Hay, Steven J. Geib, Dennis P. Curran, and Matthew G. LaPorte
Organic Letters 2014 Volume 16(Issue 1) pp:94-97
Publication Date(Web):December 6, 2013
DOI:10.1021/ol403078e
A radical [3 + 2]-divinylcyclopropane annulation cascade has been extended to encompass five D-ring variants of the meloscine/epimeloscine core structure. Representative ABCD tetracyclic intermediates were further elaborated with novel substituted E-rings through subsequent transformations of advanced intermediates that provided opportunities for late-stage variation of the B-ring (lactam) N-substituents which were also developed.
Co-reporter:Matthew G. LaPorte, Dimas José da Paz Lima, Feng Zhang, Malabika Sen, Jennifer R. Grandis, Daniel Camarco, Yun Hua, Paul A. Johnston, John S. Lazo, Lynn O. Resnick, Peter Wipf, Donna M. Huryn
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 21) pp:5081-5085
Publication Date(Web):1 November 2014
DOI:10.1016/j.bmcl.2014.09.001
Synthesis and SAR investigation of 2-guanidinoquinazolines, initially identified in a high content screen for selective STAT3 pathway inhibitors, led to a more potent analog (11c) that demonstrated improved anti-proliferative activity against a panel of HNSCC cell lines.Graphical abstract
Co-reporter:Matthew G. LaPorte, Sammi Tsegay, Ki Bum Hong, Chunliang Lu, Cheng Fang, Lirong Wang, Xiang-Qun Xie, and Paul E. Floreancig
ACS Combinatorial Science 2013 Volume 15(Issue 7) pp:344
Publication Date(Web):June 3, 2013
DOI:10.1021/co4000387
A library of spirooxindoles containing varied elements of structural and stereochemical diversity has been constructed via a three step, one pot nitrile hydrozirconation-acylation-cyclization reaction sequence from common acyclic indole intermediates. The resulting library was evaluated for novelty through comparison with MLSMR and Maybridge compound collections.Keywords: nitrile hydrozirconation-acylation-cyclization cascade; spirooxindoles
Co-reporter:Randy W. Jackson, Matthew G. LaPorte, Torsten Herbertz, Tandy L. Draper, Janet A. Gaboury, Susan R. Rippin, Ravi Patel, Srinivas K. Chunduru, Christopher A. Benetatos, Dorothy C. Young, Christopher J. Burns, Stephen M. Condon
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 11) pp:3227-3231
Publication Date(Web):1 June 2011
DOI:10.1016/j.bmcl.2011.04.052
We describe the structure–activity relationship of the C7-position of pyrano[3,4-b]indole-based inhibitors of HCV NS5B polymerase. Further exploration of the allosteric binding site led to the discovery of the significantly more potent compounds 13 and 14.We describe the structure–activity relationship of the C7-position of pyrano[3,4-b]indole-based inhibitors of HCV NS5B polymerase. Further exploration of the allosteric binding site led to the discovery of the significantly more potent compounds 13 and 14.
Co-reporter:Matthew G. LaPorte, Tandy L. Draper, Lori E. Miller, Charles W. Blackledge, Lara K. Leister, Eugene Amparo, Alison R. Hussey, Dorothy C. Young, Srinivas K. Chunduru, Christopher A. Benetatos, Gerry Rhodes, Ariamala Gopalsamy, Torsten Herbertz, Christopher J. Burns, Stephen M. Condon
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 9) pp:2968-2973
Publication Date(Web):1 May 2010
DOI:10.1016/j.bmcl.2010.03.002
We describe the structure–activity relationship of the C1-group of pyrano[3,4-b]indole based inhibitors of HCV NS5B polymerase. Further exploration of the allosteric binding site led to the discovery of the significantly more potent compound 12.We describe the structure–activity relationship of the C1-group of pyrano[3,4-b]indole based inhibitors of HCV NS5B polymerase. Further exploration of the allosteric binding site led to the discovery of the significantly more potent compound 12.
