Literature DB >> 12467630

1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists: modifications of the arylpropylpiperidine side chains.

Christopher L Lynch1, Christopher A Willoughby, Jeffrey J Hale, Edward J Holson, Richard J Budhu, Amy L Gentry, Keith G Rosauer, Charles G Caldwell, Ping Chen, Sander G Mills, Malcolm MacCoss, Scott Berk, Liya Chen, Kevin T Chapman, Lorraine Malkowitz, Martin S Springer, Sandra L Gould, Julie A DeMartino, Salvatore J Siciliano, Margaret A Cascieri, Anthony Carella, Gwen Carver, Karen Holmes, William A Schleif, Renee Danzeisen, Daria Hazuda, Joseph Kessler, Janet Lineberger, Michael Miller, Emilio A Emini.   

Abstract

The 4-(3-phenylprop-1-yl)piperidine moiety of the 1,3,4-trisubstituted pyrrolidine CCR5 antagonist 1 was modified with electron deficient aromatics as well as replacement of the benzylic methylene with sulfones, gem-difluoromethylenes and alcohols in an effort to balance the antiviral potency with reasonable pharmacokinetics.

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Year:  2003        PMID: 12467630     DOI: 10.1016/s0960-894x(02)00829-6

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  5 in total

1.  Controlling the Cleavage of Carbon-Carbon Bonds To Generate α,α-Difluorobenzyl Carbanions for the Construction of Difluoromethylbenzenes.

Authors:  Hari R Khatri; Changho Han; Erica Luong; Xiaoliang Pan; Amna T Adam; Maali D Alshammari; Yihan Shao; David A Colby
Journal:  J Org Chem       Date:  2019-09-06       Impact factor: 4.354

2.  Anibamine, a natural product CCR5 antagonist, as a novel lead for the development of anti-prostate cancer agents.

Authors:  Xueping Zhang; Kendra M Haney; Amanda C Richardson; Eden Wilson; David A Gewirtz; Joy L Ware; Zendra E Zehner; Yan Zhang
Journal:  Bioorg Med Chem Lett       Date:  2010-06-08       Impact factor: 2.823

3.  Radical Retrosynthesis.

Authors:  Joel M Smith; Stephen J Harwood; Phil S Baran
Journal:  Acc Chem Res       Date:  2018-08-02       Impact factor: 22.384

4.  Comparative docking study of anibamine as the first natural product CCR5 antagonist in CCR5 homology models.

Authors:  Guo Li; Kendra M Haney; Glen E Kellogg; Yan Zhang
Journal:  J Chem Inf Model       Date:  2009-01       Impact factor: 4.956

5.  Selective single C-F bond arylation of trifluoromethylalkene derivatives.

Authors:  Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

  5 in total

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