Literature DB >> 24900242

Benzimidazole-2-pyrazole HIF Prolyl 4-Hydroxylase Inhibitors as Oral Erythropoietin Secretagogues.

Mark D Rosen1, Hariharan Venkatesan1, Hillary M Peltier1, Scott D Bembenek1, Kimon C Kanelakis1, Lucy X Zhao1, Barry E Leonard1, Frances M Hocutt1, Xiaodong Wu1, Heather L Palomino1, Theresa I Brondstetter1, Peter V Haugh1, Laurence Cagnon1, Wen Yan1, Lisa A Liotta1, Andrew Young1, Tara Mirzadegan1, Nigel P Shankley1, Terrance D Barrett1, Michael H Rabinowitz1.   

Abstract

HIF prolyl 4-hydroxylases (PHD) are a family of enzymes that mediate key physiological responses to hypoxia by modulating the levels of hypoxia inducible factor 1-α (HIF1α). Certain benzimidazole-2-pyrazole carboxylates were discovered to be PHD2 inhibitors using ligand- and structure-based methods and found to be potent, orally efficacious stimulators of erythropoietin secretion in vivo.

Entities:  

Keywords:  HIF; PHD inhibitors; Prolyl 4-hydroxylase inhibitors; anemia; epo; erythropoietin; erythropoietin stimulating agents; hypoxia inducible factor

Year:  2010        PMID： 24900242      PMCID： PMC4007848          DOI： 10.1021/ml100198y

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  24 in total

1.  2-oxoglutarate analogue inhibitors of HIF prolyl hydroxylase.

Authors:  David R Mole; Imre Schlemminger; Luke A McNeill; Kirsty S Hewitson; Christopher W Pugh; Peter J Ratcliffe; Christopher J Schofield
Journal:  Bioorg Med Chem Lett       Date:  2003-08-18       Impact factor: 2.823

2.  Design and synthesis of a series of novel pyrazolopyridines as HIF-1alpha prolyl hydroxylase inhibitors.

Authors:  Namal C Warshakoon; Shengde Wu; Angelique Boyer; Richard Kawamoto; Sean Renock; Kevin Xu; Matthew Pokross; Artem G Evdokimov; Songtao Zhou; Carol Winter; Richard Walter; Marlene Mekel
Journal:  Bioorg Med Chem Lett       Date:  2006-11-01       Impact factor: 2.823

3.  A novel series of imidazo[1,2-a]pyridine derivatives as HIF-1alpha prolyl hydroxylase inhibitors.

Authors:  Namal C Warshakoon; Shengde Wu; Angelique Boyer; Richard Kawamoto; Justin Sheville; Sean Renock; Kevin Xu; Matthew Pokross; Artem G Evdokimov; Richard Walter; Marlene Mekel
Journal:  Bioorg Med Chem Lett       Date:  2006-09-08       Impact factor: 2.823

Review 4.  Hypoxia inducible factor prolyl 4-hydroxylase enzymes: center stage in the battle against hypoxia, metabolic compromise and oxidative stress.

Authors:  Ambreena Siddiq; Leila R Aminova; Rajiv R Ratan
Journal:  Neurochem Res       Date:  2007-03-07       Impact factor: 3.996

Review 5.  In vivo functions of the prolyl-4-hydroxylase domain oxygen sensors: direct route to the treatment of anaemia and the protection of ischaemic tissues.

Authors:  D M Katschinski
Journal:  Acta Physiol (Oxf)       Date:  2009-01-24       Impact factor: 6.311

6.  HIFalpha targeted for VHL-mediated destruction by proline hydroxylation: implications for O2 sensing.

Authors:  M Ivan; K Kondo; H Yang; W Kim; J Valiando; M Ohh; A Salic; J M Asara; W S Lane; W G Kaelin
Journal:  Science       Date:  2001-04-05       Impact factor: 47.728

7.  The prolyl 4-hydroxylase inhibitor ethyl-3,4-dihydroxybenzoate generates effective iron deficiency in cultured cells.

Authors:  Jian Wang; Joan L Buss; Guohua Chen; Prem Ponka; Kostas Pantopoulos
Journal:  FEBS Lett       Date:  2002-10-09       Impact factor: 4.124

8.  Dipeptidyl-quinolone derivatives inhibit hypoxia inducible factor-1α prolyl hydroxylases-1, -2, and -3 with altered selectivity.

Authors:  Justin K Murray; Chenera Balan; Alan M Allgeier; Annie Kasparian; Vellarkad Viswanadhan; Christopher Wilde; Jennifer R Allen; Sean C Yoder; Gloria Biddlecome; Randall W Hungate; Les P Miranda
Journal:  J Comb Chem       Date:  2010-09-13

9.  2-trihalogenomethylbenzazoles. 3. Reactions of 2-trichloromethylbenzimidazole with nucleophiles.

Authors:  B C Ennis; G Holan; E L Samuel
Journal:  J Chem Soc Perkin 1       Date:  1967

10.  Transport of iron and other transition metals into cells as revealed by a fluorescent probe.

Authors:  W Breuer; S Epsztejn; P Millgram; I Z Cabantchik
Journal:  Am J Physiol       Date:  1995-06
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  17 in total

1.  Inverse solvent isotope effects demonstrate slow aquo release from hypoxia inducible factor-prolyl hydroxylase (PHD2).

Authors:  Shannon C Flagg; Nitai Giri; Serap Pektas; Michael J Maroney; Michael J Knapp
Journal:  Biochemistry       Date:  2012-08-09       Impact factor: 3.162

2.  Increased Turnover at Limiting O2 Concentrations by the Thr(387) → Ala Variant of HIF-Prolyl Hydroxylase PHD2.

Authors:  Serap Pektas; Cornelius Y Taabazuing; Michael J Knapp
Journal:  Biochemistry       Date:  2015-04-28       Impact factor: 3.162

3.  Affinity-Based Fluorescence Polarization Assay for High-Throughput Screening of Prolyl Hydroxylase 2 Inhibitors.

Authors:  Yonghua Lei; Tianhan Hu; Xingsen Wu; Yue Wu; Qichao Bao; Lianshan Zhang; Hua Xia; Haopeng Sun; Qidong You; Xiaojin Zhang
Journal:  ACS Med Chem Lett       Date:  2015-11-09       Impact factor: 4.345

4.  Screening chelating inhibitors of HIF-prolyl hydroxylase domain 2 (PHD2) and factor inhibiting HIF (FIH).

Authors:  Shannon C Flagg; Cristina B Martin; Cornelius Y Taabazuing; Breanne E Holmes; Michael J Knapp
Journal:  J Inorg Biochem       Date:  2012-03-17       Impact factor: 4.155

5.  Prolyl hydroxylase inhibition corrects functional iron deficiency and inflammation-induced anaemia in rats.

Authors:  Terrance D Barrett; Heather L Palomino; Theresa I Brondstetter; Kimon C Kanelakis; Xiaodong Wu; Wen Yan; Katherine P Merton; Freddy Schoetens; Jing Ying Ma; Judy Skaptason; Jingjin Gao; Da-Thao Tran; Hariharan Venkatesan; Mark D Rosen; Nigel P Shankley; Michael H Rabinowitz
Journal:  Br J Pharmacol       Date:  2015-06-26       Impact factor: 8.739

6.  Discovery of a new molecular probe ML228: an activator of the hypoxia inducible factor (HIF) pathway.

Authors:  Jimmy R Theriault; Andrew S Felts; Brittney S Bates; Jose R Perez; Michelle Palmer; Shawn R Gilbert; Eric S Dawson; Julie L Engers; Craig W Lindsley; Kyle A Emmitte
Journal:  Bioorg Med Chem Lett       Date:  2011-11-28       Impact factor: 2.823

Review 7.  Imposing function down a (cupin)-barrel: secondary structure and metal stereochemistry in the αKG-dependent oxygenases.

Authors:  John A Hangasky; Cornelius Y Taabazuing; Meaghan A Valliere; Michael J Knapp
Journal:  Metallomics       Date:  2013-04       Impact factor: 4.526

8.  Structural investigations of the nickel-induced inhibition of truncated constructs of the JMJD2 family of histone demethylases using X-ray absorption spectroscopy.

Authors:  Nitai Charan Giri; Lisa Passantino; Hong Sun; Maria Antonietta Zoroddu; Max Costa; Michael J Maroney
Journal:  Biochemistry       Date:  2013-06-07       Impact factor: 3.162

Review 9.  Recent examples of α-ketoglutarate-dependent mononuclear non-haem iron enzymes in natural product biosyntheses.

Authors:  Shu-Shan Gao; Nathchar Naowarojna; Ronghai Cheng; Xueting Liu; Pinghua Liu
Journal:  Nat Prod Rep       Date:  2018-08-15       Impact factor: 13.423

10.  Dual-action inhibitors of HIF prolyl hydroxylases that induce binding of a second iron ion.

Authors:  Kar Kheng Yeoh; Mun Chiang Chan; Armin Thalhammer; Marina Demetriades; Rasheduzzaman Chowdhury; Ya-Min Tian; Ineke Stolze; Luke A McNeill; Myung Kyu Lee; Esther C Y Woon; Mukram M Mackeen; Akane Kawamura; Peter J Ratcliffe; Jasmin Mecinović; Christopher J Schofield
Journal:  Org Biomol Chem       Date:  2012-11-15       Impact factor: 3.876
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