Literature DB >> 11511245

Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine: convergent synthesis of the aza-C-nucleoside immucillins.

G B Evans1, R H Furneaux, T L Hutchison, H S Kezar, P E Morris, V L Schramm, P C Tyler.   

Abstract

Means have been developed for the synthesis and addition of 9-deaza-9-lithiopurine derivatives to the carbohydrate-derived cyclic imine 6 in facile convergent syntheses of biologically active aza-C-nucleosides.

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Year:  2001        PMID： 11511245     DOI： 10.1021/jo0155613

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


  10 in total

1.  Synthesis of 2'-deoxy-9-deaza nucleosides using Heck methodology.

Authors:  Kartik Temburnikar; Kelin Brace; Katherine L Seley-Radtke
Journal:  J Org Chem       Date:  2013-07-05       Impact factor: 4.354

Review 2.  Enzymatic transition states, transition-state analogs, dynamics, thermodynamics, and lifetimes.

Authors:  Vern L Schramm
Journal:  Annu Rev Biochem       Date:  2011       Impact factor: 23.643

3.  Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines.

Authors:  Kartik W Temburnikar; Sarah C Zimmermann; Nathaniel T Kim; Christina R Ross; Christopher Gelbmann; Christine E Salomon; Gerald M Wilson; Jan Balzarini; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem       Date:  2014-03-03       Impact factor: 3.641

4.  Four generations of transition-state analogues for human purine nucleoside phosphorylase.

Authors:  Meng-Chiao Ho; Wuxian Shi; Agnes Rinaldo-Matthis; Peter C Tyler; Gary B Evans; Keith Clinch; Steven C Almo; Vern L Schramm
Journal:  Proc Natl Acad Sci U S A       Date:  2010-03-08       Impact factor: 11.205

5.  A proof-of-principle pharmacokinetic, pharmacodynamic, and clinical study with purine nucleoside phosphorylase inhibitor immucillin-H (BCX-1777, forodesine).

Authors:  Varsha Gandhi; John M Kilpatrick; William Plunkett; Mary Ayres; Leigh Harman; Min Du; Shanta Bantia; Jan Davisson; William G Wierda; Stefan Faderl; Hagop Kantarjian; Deborah Thomas
Journal:  Blood       Date:  2005-08-30       Impact factor: 22.113

6.  Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines.

Authors:  Kartik W Temburnikar; Christina R Ross; Gerald M Wilson; Jan Balzarini; Brian M Cawrse; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem       Date:  2015-06-16       Impact factor: 3.641

7.  Intracellular rebinding of transition-state analogues provides extended in vivo inhibition lifetimes on human purine nucleoside phosphorylase.

Authors:  Sara T Gebre; Scott A Cameron; Lei Li; Y S Babu; Vern L Schramm
Journal:  J Biol Chem       Date:  2017-08-09       Impact factor: 5.157

8.  Immucillins in custom catalytic-site cavities.

Authors:  Andrew S Murkin; Keith Clinch; Jennifer M Mason; Peter C Tyler; Vern L Schramm
Journal:  Bioorg Med Chem Lett       Date:  2008-08-19       Impact factor: 2.823

9.  Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics.

Authors:  Keith Clinch; Gary B Evans; Richard F G Fröhlich; Shivali A Gulab; Jemy A Gutierrez; Jennifer M Mason; Vern L Schramm; Peter C Tyler; Anthony D Woolhouse
Journal:  Bioorg Med Chem       Date:  2012-07-14       Impact factor: 3.641

10.  Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars.

Authors:  Milan Bergeron-Brlek; Michael Meanwell; Robert Britton
Journal:  Nat Commun       Date:  2015-04-23       Impact factor: 14.919
  10 in total

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