Literature DB >> 19703776

Synthesis and antimalarial activity of new chloroquine analogues carrying a multifunctional linear side chain.

Daniel P Iwaniuk1, Eric D Whetmore, Nicholas Rosa, Kekeli Ekoue-Kovi, John Alumasa, Angel C de Dios, Paul D Roepe, Christian Wolf.   

Abstract

We report the synthesis and in vitro antimalarial activity of several new 4-amino- and 4-alkoxy-7-chloroquinolines carrying a linear dibasic side chain. Many of these chloroquine analogues have submicromolar antimalarial activity versus HB3 (chloroquine sensitive) and Dd2 (chloroquine resistant strain of Plasmodium falciparum) and low resistance indices were obtained in most cases. Importantly, compounds 11-15 and 24 proved to be more potent against Dd2 than chloroquine. Branching of the side chain structure proved detrimental to the activity against the CQR strain.

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Year:  2009        PMID： 19703776      PMCID： PMC2749251          DOI： 10.1016/j.bmc.2009.08.003

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


  25 in total

Review 1.  Medical need, scientific opportunity and the drive for antimalarial drugs.

Authors:  Robert G Ridley
Journal:  Nature       Date:  2002-02-07       Impact factor: 49.962

2.  Structure-activity relationships in 4-aminoquinoline antiplasmodials. The role of the group at the 7-position.

Authors:  Catherine H Kaschula; Timothy J Egan; Roger Hunter; Nicoletta Basilico; Silvia Parapini; Donatella Taramelli; Erica Pasini; Diego Monti
Journal:  J Med Chem       Date:  2002-08-01       Impact factor: 7.446

Review 3.  Chemotherapeutic agents against malaria: what next after chloroquine?

Authors:  José N Domínguez
Journal:  Curr Top Med Chem       Date:  2002-11       Impact factor: 3.295

4.  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

5.  Novel short chain chloroquine analogues retain activity against chloroquine resistant K1 Plasmodium falciparum.

Authors:  Paul A Stocks; Kaylene J Raynes; Patrick G Bray; B Kevin Park; Paul M O'Neill; Stephen A Ward
Journal:  J Med Chem       Date:  2002-11-07       Impact factor: 7.446

6.  Structure-function relationships in aminoquinolines: effect of amino and chloro groups on quinoline-hematin complex formation, inhibition of beta-hematin formation, and antiplasmodial activity.

Authors:  T J Egan; R Hunter; C H Kaschula; H M Marques; A Misplon; J Walden
Journal:  J Med Chem       Date:  2000-01-27       Impact factor: 7.446

Review 7.  The neglected burden of Plasmodium vivax malaria.

Authors:  K Mendis; B J Sina; P Marchesini; R Carter
Journal:  Am J Trop Med Hyg       Date:  2001 Jan-Feb       Impact factor: 2.345

8.  Solution structures of antimalarial drug-heme complexes.

Authors:  Alison Leed; Kateri DuBay; Lyann M B Ursos; Devin Sears; Angel C De Dios; Paul D Roepe
Journal:  Biochemistry       Date:  2002-08-13       Impact factor: 3.162

9.  Inhibition of heme crystal growth by antimalarials and other compounds: implications for drug discovery.

Authors:  Curtis Robert Chong; David Joseph Sullivan
Journal:  Biochem Pharmacol       Date:  2003-12-01       Impact factor: 5.858

10.  Carbon isosteres of the 4-aminopyridine substructure of chloroquine: effects on pK(a), hematin binding, inhibition of hemozoin formation, and parasite growth.

Authors:  Srinivasa R Cheruku; Souvik Maiti; Arnulf Dorn; Bernard Scorneaux; Apurba K Bhattacharjee; William Y Ellis; Jonathan L Vennerstrom
Journal:  J Med Chem       Date:  2003-07-03       Impact factor: 7.446
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  8 in total

1.  A chemotype that inhibits three unrelated pathogenic targets: the botulinum neurotoxin serotype A light chain, P. falciparum malaria, and the Ebola filovirus.

Authors:  Igor Opsenica; James C Burnett; Rick Gussio; Dejan Opsenica; Nina Todorović; Charlotte A Lanteri; Richard J Sciotti; Montip Gettayacamin; Nicoletta Basilico; Donatella Taramelli; Jonathan E Nuss; Laura Wanner; Rekha G Panchal; Bogdan A Solaja; Sina Bavari
Journal:  J Med Chem       Date:  2011-01-25       Impact factor: 7.446

2.  Novel 4-aminoquinoline analogs highly active against the blood and sexual stages of Plasmodium in vivo and in vitro.

Authors:  Fabián E Sáenz; Tina Mutka; Kenneth Udenze; Ayoade M J Oduola; Dennis E Kyle
Journal:  Antimicrob Agents Chemother       Date:  2012-06-18       Impact factor: 5.191

3.  Cytostatic versus cytocidal activities of chloroquine analogues and inhibition of hemozoin crystal growth.

Authors:  Alexander P Gorka; John N Alumasa; Katy S Sherlach; Lauren M Jacobs; Katherine B Nickley; Jonathan P Brower; Angel C de Dios; Paul D Roepe
Journal:  Antimicrob Agents Chemother       Date:  2012-10-31       Impact factor: 5.191

4.  The development and validation of an LC-MS/MS method for the determination of a new anti-malarial compound (TK900D) in human whole blood and its application to pharmacokinetic studies in mice.

Authors:  Efrem T Abay; Jan H van der Westhuizen; Kenneth J Swart; Liezl Gibhard; Matshawandile Tukulula; Kelly Chibale; Lubbe Wiesner
Journal:  Malar J       Date:  2014-01-31       Impact factor: 2.979

5.  Identification of β-hematin inhibitors in a high-throughput screening effort reveals scaffolds with in vitro antimalarial activity.

Authors:  Rebecca D Sandlin; Kim Y Fong; Kathryn J Wicht; Holly M Carrell; Timothy J Egan; David W Wright
Journal:  Int J Parasitol Drugs Drug Resist       Date:  2014-09-11       Impact factor: 4.077

6.  Antiplasmodial activity of chloroquine analogs against chloroquine-resistant parasites, docking studies and mechanisms of drug action.

Authors:  Nicolli B de Souza; Arturene M L Carmo; Adilson D da Silva; Tanos C C França; Antoniana U Krettli
Journal:  Malar J       Date:  2014-12-02       Impact factor: 2.979

7.  New trifluoromethyl triazolopyrimidines as anti-Plasmodium falciparum agents.

Authors:  Núbia Boechat; Luiz C S Pinheiro; Thiago S Silva; Anna C C Aguiar; Alcione S Carvalho; Monica M Bastos; Carolina C P Costa; Sergio Pinheiro; Angelo C Pinto; Jorge S Mendonça; Karen D B Dutra; Alessandra L Valverde; Osvaldo A Santos-Filho; Isabela P Ceravolo; Antoniana U Krettli
Journal:  Molecules       Date:  2012-07-10       Impact factor: 4.411

8.  Development of potent autophagy inhibitors that sensitize oncogenic BRAF V600E mutant melanoma tumor cells to vemurafenib.

Authors:  Megan L Goodall; Tong Wang; Katie R Martin; Matthew G Kortus; Audra L Kauffman; Jeffrey M Trent; Stephen Gately; Jeffrey P MacKeigan
Journal:  Autophagy       Date:  2014-06       Impact factor: 16.016
  8 in total

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