Reversible and competitive cinnamoyl triazole inhibitors of tissue transglutaminase

Chemical Biology & Drug Design
Christophe PardinJeffrey W Keillor

Abstract

A series of 15 cinnamoyl triazole derivatives was prepared by Cu(I)-catalyzed azide/alkyne [3+2]-cycloaddition reactions and examined as inhibitors of guinea-pig liver transglutaminase. Several compounds exhibited activity as reversible inhibitors that were competitive with acyl donor transglutaminase substrates. For example, triazole 4d has a K(i) value of 174 nM and represents one of the most potent reversible transglutaminase inhibitors reported to date.

References

Dec 1, 1991·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·C S GreenbergR H Rice
Dec 12, 2001·Neurochemistry International·Marcela V KarpujLawrence Steinman
Dec 12, 2001·Neurochemistry International·Soo Youl KimPeter M Steinert
Nov 13, 2003·Chembiochem : a European Journal of Chemical Biology·Ashraf BrikChi-Huey Wong
Dec 18, 2003·Drug Discovery Today·Hartmuth C Kolb, K Barry Sharpless
Jan 9, 2004·Protein Expression and Purification·Steve M F G GilletJoelle N Pelletier
Mar 11, 2004·Protein Science : a Publication of the Protein Society·Roberto A ChicaJoelle N Pelletier
Jun 3, 2004·Chembiochem : a European Journal of Chemical Biology·Michael D BestChi-Huey Wong
Nov 19, 2004·Organic Letters·Krishnamoorthy SivakumarQian Wang
Mar 23, 2005·Bioorganic & Medicinal Chemistry Letters·Eric DuvalGregory D Cuny
Jun 4, 2005·Chembiochem : a European Journal of Chemical Biology·Ashraf BrikChi-Huey Wong
Jan 6, 2006·Journal of Medicinal Chemistry·Ravindranadh V SomuCourtney C Aldrich
Jan 20, 2006·Journal of Medicinal Chemistry·Francesca PagliaiArmando A Genazzani
Dec 15, 2006·Organic Letters·Thanh LuuRik R Tykwinski
Jun 28, 2008·The Journal of Organic Chemistry·Christophe PardinJeffrey W Keillor

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Citations

Nov 17, 2012·World Journal of Gastroenterology : WJG·Naiyana GujralAlan B R Thomson
Sep 12, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Johanna SzabóErzsébet Mernyák
Oct 23, 2012·Protein Expression and Purification·Isabelle RoyJeffrey W Keillor
Jan 4, 2012·Pharmacology & Therapeutics·Hilary Grosso, M Maral Mouradian
Sep 22, 2009·Gastroenterology·Detlef SchuppanDonatella Barisani
May 7, 2009·Journal of Neurochemistry·Thomas M JeitnerArthur J L Cooper
May 24, 2014·Pharmacology & Therapeutics·F I TaraziS A Mousa
Sep 29, 2011·European Journal of Medicinal Chemistry·Christophe MenendezMichel Baltas
Jan 17, 2014·Bioorganic & Medicinal Chemistry Letters·Markus PietschReik Löser
Dec 17, 2014·Trends in Pharmacological Sciences·Jeffrey W KeillorAbdullah Akbar
May 18, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Johanna SzabóErzsébet Mernyák
Apr 29, 2016·Chemistry, an Asian Journal·Raj KamalRavinder Kumar
May 4, 2011·The Journal of Organic Chemistry·Jinling HeNoritaka Mizuno
Jul 23, 2014·The Journal of Organic Chemistry·Emmanuel B Castillo-ContrerasGregory R Dake
Sep 30, 2010·The American Journal of Gastroenterology·Maud PinierJean-Christophe Leroux
Nov 2, 2019·Critical Reviews in Food Science and Nutrition·Yi Zhang, Benjamin K Simpson
Mar 1, 2012·Organic & Biomolecular Chemistry·Manjunath LamaniKandikere Ramaiah Prabhu
Oct 6, 2021·Expert Opinion on Therapeutic Targets·Jeffrey W Keillor, Gail V W Johnson

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