Literature DB >> 16759871

Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes.

Yuxiang Dong1, Yuanqing Tang, Jacques Chollet, Hugues Matile, Sergio Wittlin, Susan A Charman, William N Charman, Josefina Santo Tomas, Christian Scheurer, Christopher Snyder, Bernard Scorneaux, Saroj Bajpai, Scott A Alexander, Xiaofang Wang, Maniyan Padmanilayam, Srinivasa R Cheruku, Reto Brun, Jonathan L Vennerstrom.   

Abstract

Based on the structures of several lipophilic trioxolane antimalarial prototypes, we set out to determine which functional groups were associated with good antimalarial profiles and identify more polar (lower LogP/LogD) lead compounds with good physicochemical properties. More lipophilic trioxolanes tended to have better oral activities than their more polar counterparts. Trioxolanes with a wide range of neutral and basic, but not acidic, functional groups had good antimalarial profiles.

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Year:  2006        PMID: 16759871     DOI: 10.1016/j.bmc.2006.05.041

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


  14 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

Review 3.  Plant-derived natural product research aimed at new drug discovery.

Authors:  Hideji Itokawa; Susan L Morris-Natschke; Toshiyuki Akiyama; Kuo-Hsiung Lee
Journal:  J Nat Med       Date:  2008-04-22       Impact factor: 2.343

4.  Structure-Activity Relationship of Antischistosomal Ozonide Carboxylic Acids.

Authors:  Jianbo Wu; Xiaofang Wang; Francis C K Chiu; Cécile Häberli; David M Shackleford; Eileen Ryan; Sriraghavan Kamaraj; Vivek J Bulbule; Alexander I Wallick; Yuxiang Dong; Karen L White; Paul H Davis; Susan A Charman; Jennifer Keiser; Jonathan L Vennerstrom
Journal:  J Med Chem       Date:  2020-03-19       Impact factor: 7.446

5.  The activity of dispiro peroxides against Fasciola hepatica.

Authors:  Xiaofang Wang; Qingjie Zhao; Mireille Vargas; Yuxiang Dong; Kamaraj Sriraghavan; Jennifer Keiser; Jonathan L Vennerstrom
Journal:  Bioorg Med Chem Lett       Date:  2011-07-19       Impact factor: 2.823

Review 6.  The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.

Authors:  Lukas Wanka; Khalid Iqbal; Peter R Schreiner
Journal:  Chem Rev       Date:  2013-02-25       Impact factor: 60.622

7.  In vivo activity of aryl ozonides against Schistosoma species.

Authors:  Jennifer Keiser; Katrin Ingram; Mireille Vargas; Jacques Chollet; Xiaofang Wang; Yuxiang Dong; Jonathan L Vennerstrom
Journal:  Antimicrob Agents Chemother       Date:  2011-11-21       Impact factor: 5.191

8.  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

9.  Peroxide bond-dependent antiplasmodial specificity of artemisinin and OZ277 (RBx11160).

Authors:  Marcel Kaiser; Sergio Wittlin; Angela Nehrbass-Stuedli; Yuxiang Dong; Xiaofang Wang; Andrew Hemphill; Hugues Matile; Reto Brun; Jonathan L Vennerstrom
Journal:  Antimicrob Agents Chemother       Date:  2007-06-11       Impact factor: 5.191

10.  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

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