Literature DB >> 20443225

Synthesis and SAR of novel isoquinoline CXCR4 antagonists with potent anti-HIV activity.

John F Miller1, Kristjan S Gudmundsson, Leah D'Aurora Richardson, Stephen Jenkinson, Andrew Spaltenstein, Michael Thomson, Pat Wheelan.   

Abstract

Using AMD070 as a starting point for structural modification, a novel series of isoquinoline CXCR4 antagonists was developed. A structure-activity scan of alternate lower heterocycles led to the 3-isoquinolinyl moiety as an attractive replacement for benzimidazole. Side chain optimization in the isoquinoline series led to a number of compounds with low nanomolar anti-HIV activities and promising rat PK properties.

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Year:  2010        PMID： 20443225     DOI： 10.1016/j.bmcl.2010.03.118

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


  9 in total

1.  Discovery of N-Alkyl Piperazine Side Chain Based CXCR4 Antagonists with Improved Drug-like Properties.

Authors:  Yesim A Tahirovic; Valarie M Truax; Robert J Wilson; Edgars Jecs; Huy H Nguyen; Eric J Miller; Michelle B Kim; Katie M Kuo; Tao Wang; Chi S Sum; Mary E Cvijic; Gretchen M Schroeder; Lawrence J Wilson; Dennis C Liotta
Journal:  ACS Med Chem Lett       Date:  2018-04-09       Impact factor: 4.345

2.  Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

3.  Pharmacophore modeling, atom based 3D-QSAR and Molecular docking approaches to screen C-X-C chemokine receptor type 4 antagonists as microbicides for human immunodeficiency virus-1.

Authors:  Radhika Ramachandran; Shanmughavel Piramanyagam
Journal:  Virusdisease       Date:  2017-09-26

Review 4.  Structural Analysis of Chemokine Receptor-Ligand Interactions.

Authors:  Marta Arimont; Shan-Liang Sun; Rob Leurs; Martine Smit; Iwan J P de Esch; Chris de Graaf
Journal:  J Med Chem       Date:  2017-03-10       Impact factor: 7.446

5.  Discovery of tetrahydroisoquinoline-based CXCR4 antagonists.

Authors:  Valarie M Truax; Huanyu Zhao; Brooke M Katzman; Anthony R Prosser; Ana A Alcaraz; Manohar T Saindane; Randy B Howard; Deborah Culver; Richard F Arrendale; Prahbakar R Gruddanti; Taylor J Evers; Michael G Natchus; James P Snyder; Dennis C Liotta; Lawrence J Wilson
Journal:  ACS Med Chem Lett       Date:  2013-09-05       Impact factor: 4.345

6.  Determination of the binding mode for the cyclopentapeptide CXCR4 antagonist FC131 using a dual approach of ligand modifications and receptor mutagenesis.

Authors:  S Thiele; J Mungalpara; A Steen; M M Rosenkilde; J Våbenø
Journal:  Br J Pharmacol       Date:  2014-12       Impact factor: 8.739

7.  Synthesis and Anti-HIV Activity of a Novel Series of Isoquinoline-Based CXCR4 Antagonists.

Authors:  Mastaneh Safarnejad Shad; Sandra Claes; Eline Goffin; Tom Van Loy; Dominique Schols; Steven De Jonghe; Wim Dehaen
Journal:  Molecules       Date:  2021-10-18       Impact factor: 4.411

Review 8.  Small molecule inhibitors of CXCR4.

Authors:  Bikash Debnath; Shili Xu; Fedora Grande; Antonio Garofalo; Nouri Neamati
Journal:  Theranostics       Date:  2013-01-15       Impact factor: 11.556

9.  Synthetic Activators of Cell Migration Designed by Constructive Machine Learning.

Authors:  Dominique Bruns; Daniel Merk; Karthiga Santhana Kumar; Martin Baumgartner; Gisbert Schneider
Journal:  ChemistryOpen       Date:  2019-10-23       Impact factor: 2.911
  9 in total

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