Literature DB >> 27648672

Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates.

Robert A Matthiesen1, Veronica S Wills1, Joseph I Metzger1, Sarah A Holstein2, David F Wiemer1.   

Abstract

Isoprenoid-substituted bisphosphonates are known to serve as inhibitors of the enzyme geranylgeranyl diphosphate synthase, and their activity can be highly sensitive to olefin stereochemistry. A mixture of homogeranyl and homoneryl triazole bisphosphonates has previously demonstrated potent activity, and thus stereocontrolled syntheses of the individual isomers have been developed.

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Year:  2016        PMID： 27648672      PMCID： PMC5297151          DOI： 10.1021/acs.joc.6b01693

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  19 in total

Review 1.  Geranylgeranyl diphosphate synthase: an emerging therapeutic target.

Authors:  A J Wiemer; D F Wiemer; R J Hohl
Journal:  Clin Pharmacol Ther       Date:  2011-11-02       Impact factor: 6.875

Review 2.  The relationship between the chemistry and biological activity of the bisphosphonates.

Authors:  Frank H Ebetino; Anne-Marie L Hogan; Shuting Sun; Maria K Tsoumpra; Xuchen Duan; James T Triffitt; Aaron A Kwaasi; James E Dunford; Bobby L Barnett; Udo Oppermann; Mark W Lundy; Alan Boyde; Boris A Kashemirov; Charles E McKenna; R Graham G Russell
Journal:  Bone       Date:  2011-04-09       Impact factor: 4.398

3.  Potent Triazole Bisphosphonate Inhibitor of Geranylgeranyl Diphosphate Synthase.

Authors:  Veronica S Wills; Cheryl Allen; Sarah A Holstein; David F Wiemer
Journal:  ACS Med Chem Lett       Date:  2015-10-28       Impact factor: 4.345

4.  Total synthesis of epothilone D: the nerol/macroaldolization approach.

Authors:  Ludger A Wessjohann; Günther O Scheid; Uwe Eichelberger; Sumaira Umbreen
Journal:  J Org Chem       Date:  2013-10-22       Impact factor: 4.354

5.  Synthesis of dendritic polyglycerol anions and their efficiency toward L-selectin inhibition.

Authors:  Marie Weinhart; Dominic Gröger; Sven Enders; Jens Dernedde; Rainer Haag
Journal:  Biomacromolecules       Date:  2011-05-20       Impact factor: 6.988

6.  Ligand-controlled regiodivergent Ni-catalyzed reductive carboxylation of allyl esters with CO2.

Authors:  Toni Moragas; Josep Cornella; Ruben Martin
Journal:  J Am Chem Soc       Date:  2014-12-12       Impact factor: 15.419

7.  A new motif for inhibitors of geranylgeranyl diphosphate synthase.

Authors:  Benjamin J Foust; Cheryl Allen; Sarah A Holstein; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2016-06-10       Impact factor: 3.641

8.  Mono- and dialkyl isoprenoid bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.

Authors:  Andrew J Wiemer; Jose S Yu; Kimberly M Lamb; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2007-09-18       Impact factor: 3.641

9.  Triazole-based inhibitors of geranylgeranyltransferase II.

Authors:  Xiang Zhou; Sara V Hartman; Ella J Born; Jacqueline P Smits; Sarah A Holstein; David F Wiemer
Journal:  Bioorg Med Chem Lett       Date:  2012-12-01       Impact factor: 2.823

10.  Synthesis of isoprenoid bisphosphonate ethers through C-P bond formations: Potential inhibitors of geranylgeranyl diphosphate synthase.

Authors:  Xiang Zhou; Jacqueline E Reilly; Kathleen A Loerch; Raymond J Hohl; David F Wiemer
Journal:  Beilstein J Org Chem       Date:  2014-07-18       Impact factor: 2.883
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  12 in total

1.  In Vivo Evaluation of Isoprenoid Triazole Bisphosphonate Inhibitors of Geranylgeranyl Diphosphate Synthase: Impact of Olefin Stereochemistry on Toxicity and Biodistribution.

Authors:  Staci L Haney; Yashpal S Chhonker; Michelle L Varney; Geoffrey Talmon; Lynette M Smith; Daryl J Murry; Sarah A Holstein
Journal:  J Pharmacol Exp Ther       Date:  2019-08-16       Impact factor: 4.030

2.  ω-Hydroxy isoprenoid bisphosphonates as linkable GGDPS inhibitors.

Authors:  Nazmul H Bhuiyan; Michelle L Varney; Deep S Bhattacharya; William M Payne; Aaron M Mohs; Sarah A Holstein; David F Wiemer
Journal:  Bioorg Med Chem Lett       Date:  2019-08-20       Impact factor: 2.823

3.  Preclinical investigation of a potent geranylgeranyl diphosphate synthase inhibitor.

Authors:  Staci L Haney; Yashpal S Chhonker; Michelle L Varney; Geoffrey Talmon; Daryl J Murry; Sarah A Holstein
Journal:  Invest New Drugs       Date:  2018-03-02       Impact factor: 3.850

4.  Selective opioid growth factor receptor antagonists based on a stilbene isostere.

Authors:  David P Stockdale; Michelle B Titunick; Jessica M Biegler; Jessie L Reed; Alyssa M Hartung; David F Wiemer; Patricia J McLaughlin; Jeffrey D Neighbors
Journal:  Bioorg Med Chem       Date:  2017-06-27       Impact factor: 3.641

5.  Olefin Isomers of a Triazole Bisphosphonate Synergistically Inhibit Geranylgeranyl Diphosphate Synthase.

Authors:  Cheryl Allen; Sandhya Kortagere; Huaxiang Tong; Robert A Matthiesen; Joseph I Metzger; David F Wiemer; Sarah A Holstein
Journal:  Mol Pharmacol       Date:  2017-01-05       Impact factor: 4.436

6.  Bishomoisoprenoid triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase.

Authors:  Veronica S Wills; Joseph I Metzger; Cheryl Allen; Michelle L Varney; David F Wiemer; Sarah A Holstein
Journal:  Bioorg Med Chem       Date:  2017-03-04       Impact factor: 3.641

7.  Amides as bioisosteres of triazole-based geranylgeranyl diphosphate synthase inhibitors.

Authors:  Daniel B Goetz; Michelle L Varney; David F Wiemer; Sarah A Holstein
Journal:  Bioorg Med Chem       Date:  2020-06-30       Impact factor: 3.641

8.  α-Methylation enhances the potency of isoprenoid triazole bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.

Authors:  Robert A Matthiesen; Michelle L Varney; Pauline C Xu; Alex S Rier; David F Wiemer; Sarah A Holstein
Journal:  Bioorg Med Chem       Date:  2017-10-19       Impact factor: 3.641

Review 9.  The Hydrolysis of Phosphinates and Phosphonates: A Review.

Authors:  Nikoletta Harsági; György Keglevich
Journal:  Molecules       Date:  2021-05-11       Impact factor: 4.411

10.  Impact of α-modifications on the activity of triazole bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.

Authors:  Alisa E R Fairweather; Daniel B Goetz; Chloe M Schroeder; Nazmul H Bhuiyan; Michelle L Varney; David F Wiemer; Sarah A Holstein
Journal:  Bioorg Med Chem       Date:  2021-07-11       Impact factor: 3.461
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