Literature DB >> 17189686

Weak base dispiro-1,2,4-trioxolanes: potent antimalarial ozonides.

Yuanqing Tang1, Yuxiang Dong, Sergio Wittlin, Susan A Charman, Jacques Chollet, Francis C K Chiu, William N Charman, Hugues Matile, Heinrich Urwyler, Arnulf Dorn, Saroj Bajpai, Xiaofang Wang, Maniyan Padmanilayam, Jean M Karle, Reto Brun, Jonathan L Vennerstrom.   

Abstract

Thirty weak base 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. Amino amide trioxolanes had the best combination of antimalarial and biopharmaceutical properties. Guanidine, aminoxy, and amino acid trioxolanes had poor antimalarial activity. Lipophilic trioxolanes were less stable metabolically than their more polar counterparts.

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Year:  2006        PMID： 17189686     DOI： 10.1016/j.bmcl.2006.12.007

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  9 in total

1.  Structure-activity relationship of an ozonide carboxylic acid (OZ78) against Fasciola hepatica.

Authors:  Qingjie Zhao; Mireille Vargas; Yuxiang Dong; Lin Zhou; Xiaofang Wang; Kamaraj Sriraghavan; Jennifer Keiser; Jonathan L Vennerstrom
Journal:  J Med Chem       Date:  2010-05-27       Impact factor: 7.446

2.  Synthesis and antimalarial activity of new 4-amino-7-chloroquinolyl amides, sulfonamides, ureas and thioureas.

Authors:  Kekeli Ekoue-Kovi; Kimberly Yearick; Daniel P Iwaniuk; Jayakumar K Natarajan; John Alumasa; Angel C de Dios; Paul D Roepe; Christian Wolf
Journal:  Bioorg Med Chem       Date:  2008-11-12       Impact factor: 3.641

3.  In Vitro Susceptibility of Leishmania infantum to Artemisinin Derivatives and Selected Trioxolanes.

Authors:  Sofia Cortes; Andreia Albuquerque; Lília I L Cabral; Liliana Lopes; Lenea Campino; Maria L S Cristiano
Journal:  Antimicrob Agents Chemother       Date:  2015-05-26       Impact factor: 5.191

4.  Overcoming drug resistance to heme-targeted antimalarials by systematic side chain variation of 7-chloro-4-aminoquinolines.

Authors:  Kimberly Yearick; Kekeli Ekoue-Kovi; Daniel P Iwaniuk; Jayakumar K Natarajan; John Alumasa; Angel C de Dios; Paul D Roepe; Christian Wolf
Journal:  J Med Chem       Date:  2008-03-18       Impact factor: 7.446

5.  Acidity enhances the formation of a persistent ozonide at aqueous ascorbate/ozone gas interfaces.

Authors:  Shinichi Enami; M R Hoffmann; A J Colussi
Journal:  Proc Natl Acad Sci U S A       Date:  2008-05-16       Impact factor: 11.205

6.  4-N-, 4-S-, and 4-O-chloroquine analogues: influence of side chain length and quinolyl nitrogen pKa on activity vs chloroquine resistant malaria.

Authors:  Jayakumar K Natarajan; John N Alumasa; Kimberly Yearick; Kekeli A Ekoue-Kovi; Leah B Casabianca; Angel C de Dios; Christian Wolf; Paul D Roepe
Journal:  J Med Chem       Date:  2008-06-26       Impact factor: 7.446

Review 7.  Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products.

Authors:  Alexander O Terent'ev; Dmitry A Borisov; Vera A Vil'; Valery M Dembitsky
Journal:  Beilstein J Org Chem       Date:  2014-01-08       Impact factor: 2.883

8.  Highly active ozonides selected against drug resistant malaria.

Authors:  Lis Lobo; Bruno de Sousa; Lília Cabral; Maria Ls Cristiano; Fátima Nogueira
Journal:  Mem Inst Oswaldo Cruz       Date:  2016-06-07       Impact factor: 2.743

9.  Treatment of a chemoresistant neuroblastoma cell line with the antimalarial ozonide OZ513.

Authors:  Don W Coulter; Timothy R McGuire; John G Sharp; Erin M McIntyre; Yuxiang Dong; Xiaofang Wang; Shawn Gray; Gracey R Alexander; Nagendra K Chatuverdi; Shantaram S Joshi; Xiaoyu Chen; Jonathan L Vennerstrom
Journal:  BMC Cancer       Date:  2016-11-08       Impact factor: 4.430
  9 in total

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