Literature DB >> 23139074

C3'/C4'-Stereochemical Effects of Digitoxigenin α-L-/α-D-Glycoside in Cancer Cytotoxicity.

John W Hinds1, Sean B McKenna, Ehesan U Sharif, Hua-Yu L Wang, Novruz G Akhmedov, George A O'Doherty.   

Abstract

Sweet'n low in stereo: A Wharton reaction was employed along with a diastereoselective palladium-catalyzed glycosylation and other post-glycosylation transformations to synthesize digitoxin analogues. Cytotoxic evaluation against a panel of cancer cell lines uncovered the stereochemical and substitutional limits of the C3'/C4'-hydroxy functionality in digitoxin monosaccharide.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 23139074     DOI： 10.1002/cmdc.201200465

Source DB:  PubMed          Journal:  ChemMedChem        ISSN： 1860-7179            Impact factor:   3.466


  10 in total

1.  Influence of Sugar Amine Regiochemistry on Digitoxigenin Neoglycoside Anticancer Activity.

Authors:  Jianjun Zhang; Larissa V Ponomareva; Nitin S Nandurkar; Yaxia Yuan; Lei Fang; Chang-Guo Zhan; Jon S Thorson
Journal:  ACS Med Chem Lett       Date:  2015-08-12       Impact factor: 4.345

2.  Merremoside D: de novo synthesis of the purported structure, NMR analysis, and comparison of spectral data.

Authors:  Ehesan U Sharif; Hua-Yu Leo Wang; Novruz G Akhmedov; George A O'Doherty
Journal:  Org Lett       Date:  2013-12-19       Impact factor: 6.005

3.  Digitoxin analogues with improved anticytomegalovirus activity.

Authors:  Hongyi Cai; Hua-Yu L Wang; Rajkumar Venkatadri; De-Xue Fu; Michael Forman; Sumit O Bajaj; Hongyan Li; George A O'Doherty; Ravit Arav-Boger
Journal:  ACS Med Chem Lett       Date:  2014-01-25       Impact factor: 4.345

4.  Cryptocaryol Structure-Activity Relationship Study of Cancer Cell Cytotoxicity and Ability to Stabilize PDCD4.

Authors:  Michael F Cuccarese; Yanping Wang; Penny J Beuning; George A O'Doherty
Journal:  ACS Med Chem Lett       Date:  2014-02-17       Impact factor: 4.345

5.  Synthesis and direct comparison of the anticancer activities of phomopsolides D and E and two 7-oxa-/7-aza-analogues.

Authors:  Alhanouf Z Aljahdali; Seth A Freedman; Jana Scott; Miaosheng Li; George A O'Doherty
Journal:  Medchemcomm       Date:  2019-05-08       Impact factor: 3.597

6.  Stereochemical Structure Activity Relationship Studies (S-SAR) of Tetrahydrolipstatin.

Authors:  Xiaofan Liu; Yanping Wang; Richard I Duclos; George A O'Doherty
Journal:  ACS Med Chem Lett       Date:  2018-02-21       Impact factor: 4.345

7.  A novel use of gentamicin in the ROS-mediated sensitization of NCI-H460 lung cancer cells to various anticancer agents.

Authors:  Michael F Cuccarese; Amit Singh; Mansoor Amiji; George A O'Doherty
Journal:  ACS Chem Biol       Date:  2013-10-17       Impact factor: 5.100

8.  21-Benzylidene digoxin: a proapoptotic cardenolide of cancer cells that up-regulates Na,K-ATPase and epithelial tight junctions.

Authors:  Sayonarah C Rocha; Marco T C Pessoa; Luiza D R Neves; Silmara L G Alves; Luciana M Silva; Herica L Santos; Soraya M F Oliveira; Alex G Taranto; Moacyr Comar; Isabella V Gomes; Fabio V Santos; Natasha Paixão; Luis E M Quintas; François Noël; Antonio F Pereira; Ana C S C Tessis; Natalia L S Gomes; Otacilio C Moreira; Ruth Rincon-Heredia; Fernando P Varotti; Gustavo Blanco; Jose A F P Villar; Rubén G Contreras; Leandro A Barbosa
Journal:  PLoS One       Date:  2014-10-07       Impact factor: 3.240

9.  Ru-catalyzed sequence for the synthesis of cyclic amido-ethers.

Authors:  Barry M Trost; Ehesan U Sharif; James J Cregg
Journal:  Chem Sci       Date:  2016-09-12       Impact factor: 9.825

10.  Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.

Authors:  Michael Mulzer; Brandon J Tiegs; Yanping Wang; Geoffrey W Coates; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2014-07-18       Impact factor: 15.419
  10 in total

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