Literature DB >> 18353653

Electronically stabilized versions of the antimalarial acetal trioxanes artemether and artesunate.

Gary H Posner1, William A Maio, Alvin S Kalinda.   

Abstract

From 9-substituted DHA, several new artemisinin-derived C-10 acetal ethers and esters were prepared with either a 9-fluoro or a 9-sulfonyl substituent. The very strong inductive electron-withdrawing C-9 substituent is shown to retard considerably C-10 ionization (acid-promoted etherification) of 9-fluoro-DHA and 9-sulfonyl-DHA.

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Year:  2008        PMID： 18353653      PMCID： PMC2668193          DOI： 10.1016/j.bmc.2008.03.010

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  10 in total

1.  Artemisone--a highly active antimalarial drug of the artemisinin class.

Authors:  Richard K Haynes; Burkhard Fugmann; Jörg Stetter; Karl Rieckmann; Hans-Dietrich Heilmann; Ho-Wai Chan; Man-Ki Cheung; Wai-Lun Lam; Ho-Ning Wong; Simon L Croft; Livia Vivas; Lauren Rattray; Lindsay Stewart; Wallace Peters; Brian L Robinson; Michael D Edstein; Barbara Kotecka; Dennis E Kyle; Bernhard Beckermann; Michael Gerisch; Martin Radtke; Gabriele Schmuck; Wolfram Steinke; Ute Wollborn; Karl Schmeer; Axel Römer
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-20       Impact factor: 15.336

Review 2.  Fluoroartemisinins: metabolically more stable antimalarial artemisinin derivatives.

Authors:  Jean-Pierre Bégué; Danièle Bonnet-Delpon
Journal:  ChemMedChem       Date:  2007-05       Impact factor: 3.466

3.  Convenient access both to highly antimalaria-active 10-arylaminoartemisinins, and to 10-alkyl ethers including artemether, arteether, and artelinate.

Authors:  Richard K Haynes; Ho-Wai Chan; Wing-Yan Ho; Cliff Ki-Fung Ko; Lucia Gerena; Dennis E Kyle; Wallace Peters; Brian L Robinson
Journal:  Chembiochem       Date:  2005-04       Impact factor: 3.164

4.  Synthesis, antimalarial activity, biomimetic iron(II) chemistry, and in vivo metabolism of novel, potent C-10-phenoxy derivatives of dihydroartemisinin.

Authors:  P M O'Neill; A Miller; L P Bishop; S Hindley; J L Maggs; S A Ward; S M Roberts; F Scheinmann; A V Stachulski; G H Posner; B K Park
Journal:  J Med Chem       Date:  2001-01-04       Impact factor: 7.446

5.  Malaria-infected mice are cured by a single dose of novel artemisinin derivatives.

Authors:  Gary H Posner; Ik-Hyeon Paik; Wonsuk Chang; Kristina Borstnik; Sandra Sinishtaj; Andrew S Rosenthal; Theresa A Shapiro
Journal:  J Med Chem       Date:  2007-04-17       Impact factor: 7.446

6.  New adamantane-based spiro 1,2,4-trioxanes orally effective against rodent and simian malaria.

Authors:  Chandan Singh; Rani Kanchan; Upasana Sharma; Sunil K Puri
Journal:  J Med Chem       Date:  2007-02-08       Impact factor: 7.446

7.  Conversion of artemisinin (qinghaosu) to iso-artemisitene and to 9-epi-artemisinin1.

Authors:  N Acton; D L Klayman
Journal:  Planta Med       Date:  1987-06       Impact factor: 3.352

8.  Antimalarial and antitumor evaluation of novel C-10 non-acetal dimers of 10beta-(2-hydroxyethyl)deoxoartemisinin.

Authors:  J Prince Jeyadevan; Patrick G Bray; James Chadwick; Amy E Mercer; Aoife Byrne; Stephen A Ward; B Kevin Park; Dominic P Williams; Rick Cosstick; Jill Davies; Adrian P Higson; Ed Irving; Gary H Posner; Paul M O'Neill
Journal:  J Med Chem       Date:  2004-02-26       Impact factor: 7.446

9.  Malaria-infected mice are cured by oral administration of new artemisinin derivatives.

Authors:  Gary H Posner; Wonsuk Chang; Lindsey Hess; Lauren Woodard; Sandra Sinishtaj; Aimee R Usera; William Maio; Andrew S Rosenthal; Alvin S Kalinda; John G D'Angelo; Kimberly S Petersen; Remo Stohler; Jacques Chollet; Josefina Santo-Tomas; Christopher Snyder; Matthias Rottmann; Sergio Wittlin; Reto Brun; Theresa A Shapiro
Journal:  J Med Chem       Date:  2008-01-31       Impact factor: 7.446

10.  Structure-activity relationships of the antimalarial agent artemisinin. 7. Direct modification of (+)-artemisinin and in vivo antimalarial screening of new, potential preclinical antimalarial candidates.

Authors:  Mitchell A Avery; Maria Alvim-Gaston; Jeffrey A Vroman; Baogen Wu; Arba Ager; Wallace Peters; Brian L Robinson; William Charman
Journal:  J Med Chem       Date:  2002-09-12       Impact factor: 7.446
  10 in total
  1 in total

1.  7,9-Diaryl-1,6,8-trioxaspiro[4.5]dec-3-en-2-ones: readily accessible and highly potent anticancer compounds.

Authors:  Michael P D'Erasmo; William B Smith; Alberto Munoz; Poornima Mohandas; Andrew S Au; Jason J Marineau; Luis E N Quadri; James E Bradner; Ryan P Murelli
Journal:  Bioorg Med Chem Lett       Date:  2014-06-12       Impact factor: 2.823
  1 in total

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