Literature DB >> 11514156

Piperazine-based CCR5 antagonists as HIV-1 inhibitors. I: 2(S)-methyl piperazine as a key pharmacophore element.

J R Tagat1, S W McCombie, R W Steensma, S Lin, D V Nazareno, B Baroudy, N Vantuno, S Xu, J Liu.   

Abstract

Optimization of the piperidino-piperazines 1 and 2 provided early leads 3 and 4, which showed good activity in the CCR5-RANTES binding assay and in antiviral assays. A systematic study around these structures showed that the 2(S)-methyl piperazine is essential for CCR5 affinity, which is further enhanced by forming the 2,6-dimethyl benzamide of the piperidine.

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Year:  2001        PMID： 11514156     DOI： 10.1016/s0960-894x(01)00381-x

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


  9 in total

1.  Discovery and characterization of vicriviroc (SCH 417690), a CCR5 antagonist with potent activity against human immunodeficiency virus type 1.

Authors:  Julie M Strizki; Cecile Tremblay; Serena Xu; Lisa Wojcik; Nicole Wagner; Waldemar Gonsiorek; R William Hipkin; Chuan-Chu Chou; Catherine Pugliese-Sivo; Yushi Xiao; Jayaram R Tagat; Kathleen Cox; Tony Priestley; Steve Sorota; Wei Huang; Martin Hirsch; Gregory R Reyes; Bahige M Baroudy
Journal:  Antimicrob Agents Chemother       Date:  2005-12       Impact factor: 5.191

2.  Orphan receptor ligand discovery by pickpocketing pharmacological neighbors.

Authors:  Tony Ngo; Andrey V Ilatovskiy; Alastair G Stewart; James L J Coleman; Fiona M McRobb; R Peter Riek; Robert M Graham; Ruben Abagyan; Irina Kufareva; Nicola J Smith
Journal:  Nat Chem Biol       Date:  2016-12-19       Impact factor: 15.040

Review 3.  Heterocyclic N-Oxides - An Emerging Class of Therapeutic Agents.

Authors:  A M Mfuh; O V Larionov
Journal:  Curr Med Chem       Date:  2015       Impact factor: 4.530

4.  Analysis of the mechanism by which the small-molecule CCR5 antagonists SCH-351125 and SCH-350581 inhibit human immunodeficiency virus type 1 entry.

Authors:  Fotini Tsamis; Svetlana Gavrilov; Francis Kajumo; Christoph Seibert; Shawn Kuhmann; Tom Ketas; Alexandra Trkola; Anadan Palani; John W Clader; Jayaram R Tagat; Stuart McCombie; Bahige Baroudy; John P Moore; Thomas P Sakmar; Tatjana Dragic
Journal:  J Virol       Date:  2003-05       Impact factor: 5.103

5.  Genetic and phenotypic analyses of human immunodeficiency virus type 1 escape from a small-molecule CCR5 inhibitor.

Authors:  Shawn E Kuhmann; Pavel Pugach; Kevin J Kunstman; Joann Taylor; Robyn L Stanfield; Amy Snyder; Julie M Strizki; Janice Riley; Bahige M Baroudy; Ian A Wilson; Bette T Korber; Steven M Wolinsky; John P Moore
Journal:  J Virol       Date:  2004-03       Impact factor: 5.103

6.  The differential sensitivity of human and rhesus macaque CCR5 to small-molecule inhibitors of human immunodeficiency virus type 1 entry is explained by a single amino acid difference and suggests a mechanism of action for these inhibitors.

Authors:  Erika Billick; Christoph Seibert; Pavel Pugach; Tom Ketas; Alexandra Trkola; Michael J Endres; Nicholas J Murgolo; Elizabeth Coates; Gregory R Reyes; Bahige M Baroudy; Thomas P Sakmar; John P Moore; Shawn E Kuhmann
Journal:  J Virol       Date:  2004-04       Impact factor: 5.103

7.  Discovery of Novel CCR5 Ligands as Anticolorectal Cancer Agents by Sequential Virtual Screening.

Authors:  Mariam A El-Zohairy; Darius P Zlotos; Martin R Berger; Hassan H Adwan; Yasmine M Mandour
Journal:  ACS Omega       Date:  2021-04-16

8.  Site-Selective Suzuki-Miyaura and Sonogashira Cross Coupling Reactions of the Bis(triflate) of 2,4'-Bis(hydroxy)diphenyl Sulfone.

Authors:  Rasheed Ahmad Khera; Asad Ali; Munawar Hussain; Muhammad Farooq Ibad; Alexander Villinger; Peter Langer
Journal:  ChemCatChem       Date:  2012-02-01       Impact factor: 5.686

9.  First synthesis of 4-(arylsulfonyl)phenols by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 2-arylsulfonyl-3-ethoxy-2-en-1-ones.

Authors:  Abdolmajid Riahi; Mohanad Shkoor; Olumide Fatunsin; Mathias Lubbe; Helmut Reinke; Peter Langer
Journal:  Tetrahedron Lett       Date:  2008-11-01       Impact factor: 2.415
  9 in total

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