Literature DB >> 20718474

A concise silylamine approach to 2-amino-3-hydroxy-indoles with potent in vivo antimalaria activity.

Sameer Urgaonkar1, Joseph F Cortese, Robert H Barker, Mandy Cromwell, Adelfa E Serrano, Dyann F Wirth, Jon Clardy, Ralph Mazitschek.   

Abstract

The development of a concise strategy to access 2-amino-3-hydroxy-indoles, which are disclosed as novel antimalarials with potent in vivo activity, is reported. Starting from isatins the target compounds are synthesized in 2 steps and in good yields via oxoindole intermediates by employing tert-butyldimethylsilyl amine (TBDMSNH(2)) as previously unexplored ammonia equivalent.

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Year:  2010        PMID： 20718474      PMCID： PMC7479540          DOI： 10.1021/ol101566h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  High-throughput Plasmodium falciparum growth assay for malaria drug discovery.

Authors:  Mary Lynn Baniecki; Dyann F Wirth; Jon Clardy
Journal:  Antimicrob Agents Chemother       Date:  2006-11-20       Impact factor: 5.191

2.  Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins.

Authors:  Ryo Shintani; Mitsunori Inoue; Tamio Hayashi
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-12       Impact factor: 15.336

3.  Catalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles.

Authors:  Nadine V Hanhan; Aziza H Sahin; Toby W Chang; James C Fettinger; Annaliese K Franz
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

4.  Synthesis and structure-activity relationships of 3-aryloxindoles: a new class of calcium-dependent, large conductance potassium (maxi-K) channel openers with neuroprotective properties.

Authors:  Piyasena Hewawasam; Matthew Erway; Sandra L Moon; Jay Knipe; Harvey Weiner; Christopher G Boissard; Debra J Post-Munson; Qi Gao; Stella Huang; Valentin K Gribkoff; Nicholas A Meanwell
Journal:  J Med Chem       Date:  2002-03-28       Impact factor: 7.446

5.  Thousands of chemical starting points for antimalarial lead identification.

Authors:  Francisco-Javier Gamo; Laura M Sanz; Jaume Vidal; Cristina de Cozar; Emilio Alvarez; Jose-Luis Lavandera; Dana E Vanderwall; Darren V S Green; Vinod Kumar; Samiul Hasan; James R Brown; Catherine E Peishoff; Lon R Cardon; Jose F Garcia-Bustos
Journal:  Nature       Date:  2010-05-20       Impact factor: 49.962

6.  Rhodium-catalyzed addition of arylboronic acids to isatins: an entry to diversity in 3-aryl-3-hydroxyoxindoles.

Authors:  Patrick Y Toullec; Richard B C Jagt; Johannes G de Vries; Ben L Feringa; Adriaan J Minnaard
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

7.  New ammonia equivalents for the Pd-catalyzed amination of aryl halides.

Authors:  X Huang; S L Buchwald
Journal:  Org Lett       Date:  2001-10-18       Impact factor: 6.005

8.  Chemical genetics of Plasmodium falciparum.

Authors:  W Armand Guiguemde; Anang A Shelat; David Bouck; Sandra Duffy; Gregory J Crowther; Paul H Davis; David C Smithson; Michele Connelly; Julie Clark; Fangyi Zhu; María B Jiménez-Díaz; María S Martinez; Emily B Wilson; Abhai K Tripathi; Jiri Gut; Elizabeth R Sharlow; Ian Bathurst; Farah El Mazouni; Joseph W Fowble; Isaac Forquer; Paula L McGinley; Steve Castro; Iñigo Angulo-Barturen; Santiago Ferrer; Philip J Rosenthal; Joseph L Derisi; David J Sullivan; John S Lazo; David S Roos; Michael K Riscoe; Margaret A Phillips; Pradipsinh K Rathod; Wesley C Van Voorhis; Vicky M Avery; R Kiplin Guy
Journal:  Nature       Date:  2010-05-20       Impact factor: 49.962

9.  In vitro evaluations of antimalarial drugs and their relevance to clinical outcomes.

Authors:  Eric H Ekland; David A Fidock
Journal:  Int J Parasitol       Date:  2008-04-01       Impact factor: 3.981

10.  One-step RhCl3-catalyzed deprotection of acyclic N-allyl amides.

Authors:  Michael J Zacuto; Feng Xu
Journal:  J Org Chem       Date:  2007-07-11       Impact factor: 4.354
  10 in total
  3 in total

1.  Identification and validation of tetracyclic benzothiazepines as Plasmodium falciparum cytochrome bc1 inhibitors.

Authors:  Carolyn K Dong; Sameer Urgaonkar; Joseph F Cortese; Francisco-Javier Gamo; Jose F Garcia-Bustos; Maria J Lafuente; Vishal Patel; Leila Ross; Bradley I Coleman; Emily R Derbyshire; Clary B Clish; Adelfa E Serrano; Mandy Cromwell; Robert H Barker; Jeffrey D Dvorin; Manoj T Duraisingh; Dyann F Wirth; Jon Clardy; Ralph Mazitschek
Journal:  Chem Biol       Date:  2011-12-23

2.  Aminoindoles, a novel scaffold with potent activity against Plasmodium falciparum.

Authors:  Robert H Barker; Sameer Urgaonkar; Ralph Mazitschek; Cassandra Celatka; Renato Skerlj; Joseph F Cortese; Erin Tyndall; Hanlan Liu; Mandy Cromwell; Amar Bir Sidhu; Jose E Guerrero-Bravo; Keila N Crespo-Llado; Adelfa E Serrano; Jing-Wen Lin; Chris J Janse; Shahid M Khan; Manoj Duraisingh; Bradley I Coleman; Inigo Angulo-Barturen; María Belén Jiménez-Díaz; Noemí Magán; Vanesa Gomez; Santiago Ferrer; María Santos Martínez; Sergio Wittlin; Petros Papastogiannidis; Thomas O'Shea; Jeffrey D Klinger; Mark Bree; Edward Lee; Mikaela Levine; Roger C Wiegand; Benito Munoz; Dyann F Wirth; Jon Clardy; Ian Bathurst; Edmund Sybertz
Journal:  Antimicrob Agents Chemother       Date:  2011-03-21       Impact factor: 5.191

3.  Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis.

Authors:  Suresh Pindi; Jianbin Wu; Guigen Li
Journal:  J Org Chem       Date:  2013-03-26       Impact factor: 4.354
  3 in total

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