Literature DB >> 29348813

Synthesis and Structure-Activity Relationship Study of Biliatresone, a Plant Isoflavonoid That Causes Biliary Atresia.

Michelle A Estrada1, Xiao Zhao2, Kristin Lorent2, Alyssa Kriegermeier3, Seika A Nagao1, Simon Berritt1, Rebecca G Wells2,4,5, Michael Pack2,6, Jeffrey D Winkler1.   

Abstract

We report the first synthesis of the plant isoflavonoid biliatresone. The convergent synthesis has been applied to the synthesis of several analogs, which have facilitated the first structure-activity relationship study for this environmental toxin that, on ingestion, recapitulates the phenotype of biliary atresia.

Entities:  

Year:  2017        PMID： 29348813      PMCID： PMC5767885          DOI： 10.1021/acsmedchemlett.7b00479

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


  8 in total

Review 1.  Biliary atresia.

Authors:  Barbara Anne Haber; Pierre Russo
Journal:  Gastroenterol Clin North Am       Date:  2003-09       Impact factor: 3.806

Review 2.  Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective.

Authors:  Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Identification of a plant isoflavonoid that causes biliary atresia.

Authors:  Kristin Lorent; Weilong Gong; Kyung A Koo; Orith Waisbourd-Zinman; Sara Karjoo; Xiao Zhao; Ian Sealy; Ross N Kettleborough; Derek L Stemple; Peter A Windsor; Stephen J Whittaker; John R Porter; Rebecca G Wells; Michael Pack
Journal:  Sci Transl Med       Date:  2015-05-06       Impact factor: 17.956

4.  Biliatresone, a Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone.

Authors:  Kyung A Koo; Kristin Lorent; Weilong Gong; Peter Windsor; Stephen J Whittaker; Michael Pack; Rebecca G Wells; John R Porter
Journal:  Chem Res Toxicol       Date:  2015-07-20       Impact factor: 3.739

5.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

6.  Extrahepatic cholangiocyte cilia are abnormal in biliary atresia.

Authors:  Sara Karjoo; Nicholas J Hand; Lorena Loarca; Pierre A Russo; Joshua R Friedman; Rebecca G Wells
Journal:  J Pediatr Gastroenterol Nutr       Date:  2013-07       Impact factor: 2.839

7.  Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

Authors:  Darcy A Culkin; John F Hartwig
Journal:  Acc Chem Res       Date:  2003-04       Impact factor: 22.384

8.  Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.

Authors:  Nicholas C Bruno; Matthew T Tudge; Stephen L Buchwald
Journal:  Chem Sci       Date:  2013       Impact factor: 9.825
  8 in total
  3 in total

1.  Impaired Redox and Protein Homeostasis as Risk Factors and Therapeutic Targets in Toxin-Induced Biliary Atresia.

Authors:  Xiao Zhao; Kristin Lorent; Diana Escobar-Zarate; Ramakrishnan Rajagopalan; Kathleen M Loomes; Kevin Gillespie; Clementina Mesaros; Michelle A Estrada; Ian A Blair; Jeffrey D Winkler; Nancy B Spinner; Marcella Devoto; Michael Pack
Journal:  Gastroenterology       Date:  2020-06-04       Impact factor: 22.682

Review 2.  Biliatresone: progress in biliary atresia study.

Authors:  Jia-Jie Zhu; Yi-Fan Yang; Rui Dong; Shan Zheng
Journal:  World J Pediatr       Date:  2022-09-27       Impact factor: 9.186

3.  Extrahepatic cholangiocyte obstruction is mediated by decreased glutathione, Wnt and Notch signaling pathways in a toxic model of biliary atresia.

Authors:  Sophia Fried; Dafna Gilboa; Adi Har-Zahav; Pierre-Marie Lavrut; Yu Du; Sara Karjoo; Pierre Russo; Raanan Shamir; Rebecca G Wells; Orith Waisbourd-Zinman
Journal:  Sci Rep       Date:  2020-05-05       Impact factor: 4.379
  3 in total

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