Literature DB >> 16154747

Trifluoroethylamines as amide isosteres in inhibitors of cathepsin K.

W Cameron Black1, Christopher I Bayly, Dana E Davis, Sylvie Desmarais, Jean-Pierre Falgueyret, Serge Léger, Chun Sing Li, Frédéric Massé, Daniel J McKay, James T Palmer, M David Percival, Joël Robichaud, Nancy Tsou, Robert Zamboni.   

Abstract

The P2-P3 amide of dipeptide cathepsin K inhibitors can be replaced by the metabolically stable trifluoroethylamine group. The non-basic nature of the nitrogen allows the important hydrogen bond to Gly66 to be made. The resulting compounds are 10- to 20-fold more potent than the corresponding amide derivatives. Compound 8 is a 5 pM inhibitor of human cathepsin K with >10,000-fold selectivity over other cathepsins.

Entities:  

Mesh：

Substances：

Year:  2005        PMID： 16154747     DOI： 10.1016/j.bmcl.2005.07.071

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


  14 in total

1.  Optimization of dipeptidic inhibitors of cathepsin L for improved Toxoplasma gondii selectivity and CNS permeability.

Authors:  Jeffery D Zwicker; Nicolas A Diaz; Alfredo J Guerra; Paul D Kirchhoff; Bo Wen; Duxin Sun; Vern B Carruthers; Scott D Larsen
Journal:  Bioorg Med Chem Lett       Date:  2018-03-09       Impact factor: 2.823

2.  Trifluoromethylation of Secondary Nitroalkanes.

Authors:  Amber A S Gietter-Burch; Vijayarajan Devannah; Donald A Watson
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

Review 3.  Amide Bond Bioisosteres: Strategies, Synthesis, and Successes.

Authors:  Shikha Kumari; Angelica V Carmona; Amit K Tiwari; Paul C Trippier
Journal:  J Med Chem       Date:  2020-08-04       Impact factor: 7.446

4.  Synthesis and Opioid Activity of Tyr1 -ψ[(Z)CF=CH]-Gly2 and Tyr1 -ψ[(S)/(R)-CF3 CH-NH]-Gly2 Leu-enkephalin Fluorinated Peptidomimetics.

Authors:  Somnath Narayan Karad; Mohan Pal; Rachel S Crowley; Thomas E Prisinzano; Ryan A Altman
Journal:  ChemMedChem       Date:  2017-04-05       Impact factor: 3.466

5.  Bioisostere Effects on the EPSA of Common Permeability-Limiting Groups.

Authors:  Andrew K Ecker; Dorothy A Levorse; Daniel A Victor; Matthew J Mitcheltree
Journal:  ACS Med Chem Lett       Date:  2022-05-23       Impact factor: 4.632

6.  Amino-oxetanes as amide isosteres by an alternative defluorosulfonylative coupling of sulfonyl fluorides.

Authors:  Juan J Rojas; Rosemary A Croft; Alistair J Sterling; Edward L Briggs; Daniele Antermite; Daniel C Schmitt; Luka Blagojevic; Peter Haycock; Andrew J P White; Fernanda Duarte; Chulho Choi; James J Mousseau; James A Bull
Journal:  Nat Chem       Date:  2022-01-27       Impact factor: 24.274

7.  2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors.

Authors:  Truong Thanh Tung; Thang Nguyen Quoc
Journal:  RSC Med Chem       Date:  2021-09-08

8.  Reversible cysteine protease inhibitors show promise for a Chagas disease cure.

Authors:  Momar Ndao; Christian Beaulieu; W Cameron Black; Elise Isabel; Fabio Vasquez-Camargo; Milli Nath-Chowdhury; Frédéric Massé; Christophe Mellon; Nathalie Methot; Deborah A Nicoll-Griffith
Journal:  Antimicrob Agents Chemother       Date:  2013-12-09       Impact factor: 5.191

9.  Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

Authors:  Chibueze I Onyeagusi; Steven J Malcolmson
Journal:  ACS Catal       Date:  2020-10-12       Impact factor: 13.084

10.  Tyr1-ψ[( Z)CF═CH]-Gly2 Fluorinated Peptidomimetic Improves Distribution and Metabolism Properties of Leu-Enkephalin.

Authors:  Ryan A Altman; Krishna K Sharma; Lian G Rajewski; Paul C Toren; Michael J Baltezor; Mohan Pal; Somnath N Karad
Journal:  ACS Chem Neurosci       Date:  2018-04-19       Impact factor: 4.418
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.