Literature DB >> 24354316

Substituted 2-phenylimidazopyridines: a new class of drug leads for human African trypanosomiasis.

Hari Babu Tatipaka1, J Robert Gillespie, Arnab K Chatterjee, Neil R Norcross, Matthew A Hulverson, Ranae M Ranade, Pendem Nagendar, Sharon A Creason, Joshua McQueen, Nicole A Duster, Advait Nagle, Frantisek Supek, Valentina Molteni, Tanja Wenzler, Reto Brun, Richard Glynne, Frederick S Buckner, Michael H Gelb.   

Abstract

A phenotypic screen of a compound library for antiparasitic activity on Trypanosoma brucei, the causative agent of human African trypanosomiasis, led to the identification of substituted 2-(3-aminophenyl)oxazolopyridines as a starting point for hit-to-lead medicinal chemistry. A total of 110 analogues were prepared, which led to the identification of 64, a substituted 2-(3-aminophenyl)imidazopyridine. This compound showed antiparasitic activity in vitro with an EC50 of 2 nM and displayed reasonable druglike properties when tested in a number of in vitro assays. The compound was orally bioavailable and displayed good plasma and brain exposure in mice. Compound 64 cured mice infected with Trypanosoma brucei when dosed orally down to 2.5 mg/kg. Given its potent antiparasitic properties and its ease of synthesis, compound 64 represents a new lead for the development of drugs to treat human African trypanosomiasis.

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Year:  2014        PMID: 24354316      PMCID: PMC3962778          DOI: 10.1021/jm401178t

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  19 in total

1.  Structure-based design of submicromolar, biologically active inhibitors of trypanosomatid glyceraldehyde-3-phosphate dehydrogenase.

Authors:  A M Aronov; S Suresh; F S Buckner; W C Van Voorhis; C L Verlinde; F R Opperdoes; W G Hol; M H Gelb
Journal:  Proc Natl Acad Sci U S A       Date:  1999-04-13       Impact factor: 11.205

2.  DNA binding affinity of bisguanidine and bis(2-aminoimidazoline) derivatives with in vivo antitrypanosomal activity.

Authors:  Christophe Dardonville; Michael P Barrett; Reto Brun; Marcel Kaiser; Farial Tanious; W David Wilson
Journal:  J Med Chem       Date:  2006-06-15       Impact factor: 7.446

3.  Evidence that suramin and aurothiomalate are teratogenic in rat by disturbing yolk sac-mediated embryonic protein nutrition.

Authors:  S J Freeman; J B Lloyd
Journal:  Chem Biol Interact       Date:  1986-05       Impact factor: 5.192

4.  The Alamar Blue assay to determine drug sensitivity of African trypanosomes (T.b. rhodesiense and T.b. gambiense) in vitro.

Authors:  B Räz; M Iten; Y Grether-Bühler; R Kaminsky; R Brun
Journal:  Acta Trop       Date:  1997-11       Impact factor: 3.112

5.  Transport of glutathione prostaglandin A conjugates by the multidrug resistance protein 1.

Authors:  R Evers; N H Cnubben; J Wijnholds; L van Deemter; P J van Bladeren; P Borst
Journal:  FEBS Lett       Date:  1997-12-08       Impact factor: 4.124

6.  Rational modification of a candidate cancer drug for use against Chagas disease.

Authors:  James M Kraus; Christophe L M J Verlinde; Mandana Karimi; Galina I Lepesheva; Michael H Gelb; Frederick S Buckner
Journal:  J Med Chem       Date:  2009-03-26       Impact factor: 7.446

7.  In vitro and in vivo reversal of multidrug resistance by GF120918, an acridonecarboxamide derivative.

Authors:  F Hyafil; C Vergely; P Du Vignaud; T Grand-Perret
Journal:  Cancer Res       Date:  1993-10-01       Impact factor: 12.701

8.  Second generation tetrahydroquinoline-based protein farnesyltransferase inhibitors as antimalarials.

Authors:  Pravin Bendale; Srinivas Olepu; Praveen Kumar Suryadevara; Vivek Bulbule; Kasey Rivas; Laxman Nallan; Brian Smart; Kohei Yokoyama; Sudha Ankala; Prakash Rao Pendyala; David Floyd; Louis J Lombardo; David K Williams; Frederick S Buckner; Debopam Chakrabarti; Christophe L M J Verlinde; Wesley C Van Voorhis; Michael H Gelb
Journal:  J Med Chem       Date:  2007-08-28       Impact factor: 7.446

9.  Efficacy, pharmacokinetics, and metabolism of tetrahydroquinoline inhibitors of Plasmodium falciparum protein farnesyltransferase.

Authors:  Wesley C Van Voorhis; Kasey L Rivas; Pravin Bendale; Laxman Nallan; Carolyn Hornéy; Lynn K Barrett; Kevin D Bauer; Brian P Smart; Sudha Ankala; Oliver Hucke; Christophe L M J Verlinde; Debopam Chakrabarti; Corey Strickland; Kohei Yokoyama; Frederick S Buckner; Andrew D Hamilton; David K Williams; Louis J Lombardo; David Floyd; Michael H Gelb
Journal:  Antimicrob Agents Chemother       Date:  2007-07-02       Impact factor: 5.191

Review 10.  Drug resistance in African trypanosomiasis: the melarsoprol and pentamidine story.

Authors:  Nicola Baker; Harry P de Koning; Pascal Mäser; David Horn
Journal:  Trends Parasitol       Date:  2013-01-30
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1.  Whole-Cell Phenotypic Screening of Medicines for Malaria Venture Pathogen Box Identifies Specific Inhibitors of Plasmodium falciparum Late-Stage Development and Egress.

Authors:  Alok Tanala Patra; Tejashri Hingamire; Meenakshi A Belekar; Aoli Xiong; Gowtham Subramanian; Zbynek Bozdech; Peter Preiser; Dhanasekaran Shanmugam; Rajesh Chandramohanadas
Journal:  Antimicrob Agents Chemother       Date:  2020-04-21       Impact factor: 5.191

Review 2.  Recent developments in drug discovery for leishmaniasis and human African trypanosomiasis.

Authors:  Advait S Nagle; Shilpi Khare; Arun Babu Kumar; Frantisek Supek; Andriy Buchynskyy; Casey J N Mathison; Naveen Kumar Chennamaneni; Nagendar Pendem; Frederick S Buckner; Michael H Gelb; Valentina Molteni
Journal:  Chem Rev       Date:  2014-11-03       Impact factor: 60.622

3.  Discovery of N-(2-aminoethyl)-N-benzyloxyphenyl benzamides: New potent Trypanosoma brucei inhibitors.

Authors:  Andriy Buchynskyy; J Robert Gillespie; Matthew A Hulverson; Joshua McQueen; Sharon A Creason; Ranae M Ranade; Nicole A Duster; Michael H Gelb; Frederick S Buckner
Journal:  Bioorg Med Chem       Date:  2016-11-12       Impact factor: 3.641

4.  Development of 5-Aminopyrazole-4-carboxamide-based Bumped-Kinase Inhibitors for Cryptosporidiosis Therapy.

Authors:  Wenlin Huang; Matthew A Hulverson; Ryan Choi; Samuel L M Arnold; Zhongsheng Zhang; Molly C McCloskey; Grant R Whitman; Robert C Hackman; Kasey L Rivas; Lynn K Barrett; Kayode K Ojo; Wesley C Van Voorhis; Erkang Fan
Journal:  J Med Chem       Date:  2019-03-15       Impact factor: 7.446

5.  Novel Bumped Kinase Inhibitors Are Safe and Effective Therapeutics in the Calf Clinical Model for Cryptosporidiosis.

Authors:  Deborah A Schaefer; Dana P Betzer; Kylie D Smith; Zachary G Millman; Hannah C Michalski; Sarah E Menchaca; Jennifer A Zambriski; Kayode K Ojo; Matthew A Hulverson; Samuel L M Arnold; Kasey L Rivas; Rama S R Vidadala; Wenlin Huang; Lynn K Barrett; Dustin J Maly; Erkang Fan; Wesley C Van Voorhis; Michael W Riggs
Journal:  J Infect Dis       Date:  2016-10-17       Impact factor: 5.226

6.  Synthesis of novel amide and urea derivatives of thiazol-2-ethylamines and their activity against Trypanosoma brucei rhodesiense.

Authors:  Donald A Patrick; Tanja Wenzler; Sihyung Yang; Patrick T Weiser; Michael Zhuo Wang; Reto Brun; Richard R Tidwell
Journal:  Bioorg Med Chem       Date:  2016-04-02       Impact factor: 3.641

7.  In Vitro and In Vivo Studies of the Trypanocidal Effect of Novel Quinolines.

Authors:  A S G Nefertiti; M M Batista; P B Da Silva; D G J Batista; C F Da Silva; R B Peres; E C Torres-Santos; E F Cunha-Junior; E Holt; D W Boykin; R Brun; T Wenzler; M N C Soeiro
Journal:  Antimicrob Agents Chemother       Date:  2018-01-25       Impact factor: 5.191

8.  Pharmacokinetics and In Vivo Efficacy of Pyrazolopyrimidine, Pyrrolopyrimidine, and 5-Aminopyrazole-4-Carboxamide Bumped Kinase Inhibitors against Toxoplasmosis.

Authors:  Matthew A Hulverson; Igor Bruzual; Erin V McConnell; Wenlin Huang; Rama S R Vidadala; Ryan Choi; Samuel L M Arnold; Grant R Whitman; Molly C McCloskey; Lynn K Barrett; Kasey L Rivas; Suzanne Scheele; Amy E DeRocher; Marilyn Parsons; Kayode K Ojo; Dustin J Maly; Erkang Fan; Wesley C Van Voorhis; J Stone Doggett
Journal:  J Infect Dis       Date:  2019-04-16       Impact factor: 5.226

9.  Triazolopyrimidines and Imidazopyridines: Structure-Activity Relationships and in Vivo Efficacy for Trypanosomiasis.

Authors:  Pendem Nagendar; J Robert Gillespie; Zackary M Herbst; Ranae M Ranade; Nora M R Molasky; Omeed Faghih; Rachael M Turner; Michael H Gelb; Frederick S Buckner
Journal:  ACS Med Chem Lett       Date:  2018-12-04       Impact factor: 4.345

10.  Bumped-Kinase Inhibitors for Cryptosporidiosis Therapy.

Authors:  Matthew A Hulverson; Sumiti Vinayak; Ryan Choi; Deborah A Schaefer; Alejandro Castellanos-Gonzalez; Rama S R Vidadala; Carrie F Brooks; Gillian T Herbert; Dana P Betzer; Grant R Whitman; Hayley N Sparks; Samuel L M Arnold; Kasey L Rivas; Lynn K Barrett; A Clinton White; Dustin J Maly; Michael W Riggs; Boris Striepen; Wesley C Van Voorhis; Kayode K Ojo
Journal:  J Infect Dis       Date:  2017-04-15       Impact factor: 5.226

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