Literature DB >> 18331795

Fluoroolefins as amide bond mimics in dipeptidyl peptidase IV inhibitors.

Scott D Edmondson1, Lan Wei, Jinyou Xu, Jackie Shang, Shiyao Xu, Jianmei Pang, Ashok Chaudhary, Dennis C Dean, Huaibing He, Barbara Leiting, Kathryn A Lyons, Reshma A Patel, Sangita B Patel, Giovanna Scapin, Joseph K Wu, Maria G Beconi, Nancy A Thornberry, Ann E Weber.   

Abstract

The synthesis, selectivity, rat pharmacokinetic profile, and drug metabolism profiles of a series of potent fluoroolefin-derived DPP-4 inhibitors (4) are reported. A radiolabeled fluoroolefin 33 was shown to possess a high propensity to form reactive metabolites, thus revealing a potential liability for this class of DPP-4 inhibitors.

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Year:  2008        PMID: 18331795     DOI: 10.1016/j.bmcl.2008.02.050

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


  8 in total

1.  Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents.

Authors:  Rui Guo; Xiaotian Qi; Hengye Xiang; Paul Geaneotes; Ruihan Wang; Peng Liu; Yi-Ming Wang
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-14       Impact factor: 15.336

2.  Palladium-Catalyzed Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes.

Authors:  Richard T Thornbury; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-11       Impact factor: 15.336

3.  Rhodium-catalysed C(sp(2))-C(sp(2)) bond formation via C-H/C-F activation.

Authors:  Panpan Tian; Chao Feng; Teck-Peng Loh
Journal:  Nat Commun       Date:  2015-06-17       Impact factor: 14.919

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.  Rhodium-Catalyzed Merging of 2-Arylquinazolinone and 2,2-Difluorovinyl Tosylate: Diverse Synthesis of Monofluoroolefin Quinazolinone Derivatives.

Authors:  Ning Wang; Qin Yang; Zhihong Deng; Xuechun Mao; Yiyuan Peng
Journal:  ACS Omega       Date:  2020-06-15

6.  Design and Synthesis of New α-hydroxy β-fluoro/β-trifluoromethyl and Unsaturated Phosphonates from Carbohydrate-Derived Building Blocks via Pudovik and Horner-Wadsworth-Emmons Reactions.

Authors:  Monika Bilska-Markowska; Wojciech Jankowski; Marcin Hoffmann; Marcin Kaźmierczak
Journal:  Molecules       Date:  2022-08-24       Impact factor: 4.927

7.  Identification of novel human dipeptidyl peptidase-IV inhibitors of natural origin (part I): virtual screening and activity assays.

Authors:  Laura Guasch; Maria José Ojeda; Noemí González-Abuín; Esther Sala; Adrià Cereto-Massagué; Miquel Mulero; Cristina Valls; Montserrat Pinent; Anna Ardévol; Santiago Garcia-Vallvé; Gerard Pujadas
Journal:  PLoS One       Date:  2012-09-12       Impact factor: 3.240

8.  A Difluoromethylene Linchpin/Synthon: Application in Conjunction with Anion Relay Chemistry (ARC) Permits Ready Access to Diverse Difluoromethylene Scaffolds.

Authors:  Kevin T O'Brien; Jonathan W Nadraws; Amos B Smith
Journal:  Org Lett       Date:  2020-11-11       Impact factor: 6.005

  8 in total

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