Literature DB >> 20031408

Aryl- and heteroaryl-substituted aminobenzo[a]quinolizines as dipeptidyl peptidase IV inhibitors.

Markus Boehringer1, Holger Fischer, Michael Hennig, Daniel Hunziker, Joerg Huwyler, Bernd Kuhn, Bernd M Loeffler, Thomas Luebbers, Patrizio Mattei, Robert Narquizian, Elena Sebokova, Urs Sprecher, Hans Peter Wessel.   

Abstract

Synthesis and SAR are described for a structurally distinct class of DPP-IV inhibitors based on aminobenzo[a]quinolizines bearing (hetero-)aromatic substituents in the S1 specificity pocket. The m-(fluoromethyl)-phenyl derivative (S,S,S)-2g possesses the best fit in the S1 pocket. However, (S,S,S)-2i, bearing a more hydrophilic 5-methyl-pyridin-2-yl residue as substituent for the S1 pocket, displays excellent in vivo activity and superior drug-like properties. Copyright (c) 2009 Elsevier Ltd. All rights reserved.

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Year:  2009        PMID： 20031408     DOI： 10.1016/j.bmcl.2009.12.025

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


  7 in total

Review 1.  A medicinal chemist's guide to molecular interactions.

Authors:  Caterina Bissantz; Bernd Kuhn; Martin Stahl
Journal:  J Med Chem       Date:  2010-07-22       Impact factor: 7.446

2.  Molecular dynamics and free energy studies of chirality specificity effects on aminobenzo[a]quinolizine inhibitors binding to DPP-IV.

Authors:  Cui Wei; Liang Desheng; Gao Jian; Luo Fang; Geng Lingling; Ji Mingjuan
Journal:  J Mol Model       Date:  2012-11-15       Impact factor: 1.810

Review 3.  Recent advances in transition metal-catalyzed Csp(2)-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation.

Authors:  Grégory Landelle; Armen Panossian; Sergiy Pazenok; Jean-Pierre Vors; Frédéric R Leroux
Journal:  Beilstein J Org Chem       Date:  2013-11-15       Impact factor: 2.883

4.  Comprehensive analysis of the Co-structures of dipeptidyl peptidase IV and its inhibitor.

Authors:  Hiroyuki Nojima; Kazuhiko Kanou; Genki Terashi; Mayuko Takeda-Shitaka; Gaku Inoue; Koichiro Atsuda; Chihiro Itoh; Chie Iguchi; Hajime Matsubara
Journal:  BMC Struct Biol       Date:  2016-08-05

5.  One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli-Cushman protocol.

Authors:  Aleksandar Pashev; Nikola Burdzhiev; Elena Stanoeva
Journal:  Beilstein J Org Chem       Date:  2020-06-24       Impact factor: 2.883

6.  Structure-Activity Relationship Studies of 4-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-6-imino-N-(naphthalen-2-yl)-1,3,5-triazin-2-amine (FPMINT) Analogues as Inhibitors of Human Equilibrative Nucleoside Transporters.

Authors:  Renkai Li; Winston Wing-Shum Mak; Jingjing Li; Chengwen Zheng; Polly Ho-Ting Shiu; Sai-Wang Seto; Simon Ming-Yuen Lee; George Pak-Heng Leung
Journal:  Front Pharmacol       Date:  2022-02-21       Impact factor: 5.810

7.  Strong nonadditivity as a key structure-activity relationship feature: distinguishing structural changes from assay artifacts.

Authors:  Christian Kramer; Julian E Fuchs; Klaus R Liedl
Journal:  J Chem Inf Model       Date:  2015-03-11       Impact factor: 4.956
  7 in total

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