Literature DB >> 22111907

Synthesis, antimalarial activity, and structure-activity relationship of 7-(2-phenoxyethoxy)-4(1H)-quinolones.

R Matthew Cross1, Niranjan K Namelikonda, Tina S Mutka, Lisa Luong, Dennis E Kyle, Roman Manetsch.   

Abstract

ICI 56,780 (5) displayed causal prophylactic and blood schizonticidal activity (ED50=0.05 mg/kg) in rodent malaria models but produced rapid acquisition of parasitological resistance in P. berghei infected mice. Herein we describe the synthesis of analogues of 5 with EC50 as low as 0.15 nM against multidrug resistant P. falciparum. Optimal activity with low cross-resistance indexes (RI) to atovaquone was achieved by introducing ortho-substituted aryl moieties at the 3-position of the 7-(2-phenoxyethoxy)-4(1H)-quinolone core.

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Year:  2011        PMID： 22111907      PMCID： PMC9247345          DOI： 10.1021/jm200718m

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   8.039


  19 in total

1.  Averting a malaria disaster.

Authors:  N J White; F Nosten; S Looareesuwan; W M Watkins; K Marsh; R W Snow; G Kokwaro; J Ouma; T T Hien; M E Molyneux; T E Taylor; C I Newbold; T K Ruebush; M Danis; B M Greenwood; R M Anderson; P Olliaro
Journal:  Lancet       Date:  1999-06-05       Impact factor: 79.321

Review 2.  Bacterial topoisomerase inhibitors: quinolone and pyridone antibacterial agents.

Authors:  Lester A Mitscher
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3.  Synthesis and structure-activity relationships of antimalarial 4-oxo-3-carboxyl quinolones.

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Journal:  Bioorg Med Chem       Date:  2010-02-11       Impact factor: 3.641

Review 4.  In vitro strategies for circumventing antimalarial drug resistance.

Authors:  W K Milhous; L Gerena; D E Kyle; A M Oduola
Journal:  Prog Clin Biol Res       Date:  1989

Review 5.  4-Quinolones: smart phones of the microbial world.

Authors:  Holly Huse; Marvin Whiteley
Journal:  Chem Rev       Date:  2010-08-11       Impact factor: 60.622

6.  Divergent route to access structurally diverse 4-quinolones via mono or sequential cross-couplings.

Authors:  R Matthew Cross; Roman Manetsch
Journal:  J Org Chem       Date:  2010-11-17       Impact factor: 4.354

7.  Endochin optimization: structure-activity and structure-property relationship studies of 3-substituted 2-methyl-4(1H)-quinolones with antimalarial activity.

Authors:  R Matthew Cross; Andrii Monastyrskyi; Tina S Mutka; Jeremy N Burrows; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2010-10-14       Impact factor: 7.446

Review 8.  New medicines to improve control and contribute to the eradication of malaria.

Authors:  Timothy N C Wells; Pedro L Alonso; Winston E Gutteridge
Journal:  Nat Rev Drug Discov       Date:  2009-10-16       Impact factor: 84.694

9.  Artemisinin resistance in Plasmodium falciparum malaria.

Authors:  Arjen M Dondorp; François Nosten; Poravuth Yi; Debashish Das; Aung Phae Phyo; Joel Tarning; Khin Maung Lwin; Frederic Ariey; Warunee Hanpithakpong; Sue J Lee; Pascal Ringwald; Kamolrat Silamut; Mallika Imwong; Kesinee Chotivanich; Pharath Lim; Trent Herdman; Sen Sam An; Shunmay Yeung; Pratap Singhasivanon; Nicholas P J Day; Niklas Lindegardh; Duong Socheat; Nicholas J White
Journal:  N Engl J Med       Date:  2009-07-30       Impact factor: 91.245

10.  Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique.

Authors:  R E Desjardins; C J Canfield; J D Haynes; J D Chulay
Journal:  Antimicrob Agents Chemother       Date:  1979-12       Impact factor: 5.191
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  14 in total

1.  4(1H)-Quinolones with liver stage activity against Plasmodium berghei.

Authors:  Alexis N Lacrue; Fabián E Sáenz; R Matthew Cross; Kenneth O Udenze; Andrii Monastyrskyi; Steven Stein; Tina S Mutka; Roman Manetsch; Dennis E Kyle
Journal:  Antimicrob Agents Chemother       Date:  2012-11-05       Impact factor: 5.191

2.  4(1H)-pyridone and 4(1H)-quinolone derivatives as antimalarials with erythrocytic, exoerythrocytic, and transmission blocking activities.

Authors:  Andrii Monastyrskyi; Dennis E Kyle; Roman Manetsch
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

3.  Design and Synthesis of Orally Bioavailable Piperazine Substituted 4(1H)-Quinolones with Potent Antimalarial Activity: Structure-Activity and Structure-Property Relationship Studies.

Authors:  Raghupathi Neelarapu; Jordany R Maignan; Cynthia L Lichorowic; Andrii Monastyrskyi; Tina S Mutka; Alexis N LaCrue; Lynn D Blake; Debora Casandra; Sherwin Mashkouri; Jeremy N Burrows; Paul A Willis; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2018-02-09       Impact factor: 7.446

Review 4.  Recent advances in malaria drug discovery.

Authors:  Marco A Biamonte; Jutta Wanner; Karine G Le Roch
Journal:  Bioorg Med Chem Lett       Date:  2013-03-27       Impact factor: 2.823

5.  4-(1H)-Quinolones and 1,2,3,4-Tetrahydroacridin-9(10H)-ones prevent the transmission of Plasmodium falciparum to Anopheles freeborni.

Authors:  Fabián E Sáenz; Alexis N Lacrue; R Matthew Cross; Jordany R Maignan; Kenneth O Udenze; Roman Manetsch; Dennis E Kyle
Journal:  Antimicrob Agents Chemother       Date:  2013-09-30       Impact factor: 5.191

6.  Progress in the Optimization of 4(1H)-Quinolone Derivatives as Antimalarials Targeting the Erythrocytic, the Exoerythrocytic and the Transmitting Stages of the Malaria Parasite.

Authors:  Fabian Brockmeyer; Roman Manetsch
Journal:  Chimia (Aarau)       Date:  2017-04-26       Impact factor: 1.656

7.  Aminoalkoxycarbonyloxymethyl Ether Prodrugs with a pH-Triggered Release Mechanism: A Case Study Improving the Solubility, Bioavailability, and Efficacy of Antimalarial 4(1H)-Quinolones with Single Dose Cures.

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Journal:  J Med Chem       Date:  2021-05-12       Impact factor: 8.039

Review 8.  Antimalarial pharmacology and therapeutics of atovaquone.

Authors:  Gemma L Nixon; Darren M Moss; Alison E Shone; David G Lalloo; Nicholas Fisher; Paul M O'Neill; Stephen A Ward; Giancarlo A Biagini
Journal:  J Antimicrob Chemother       Date:  2013-01-04       Impact factor: 5.790

9.  ICI 56,780 Optimization: Structure-Activity Relationship Studies of 7-(2-Phenoxyethoxy)-4(1H)-quinolones with Antimalarial Activity.

Authors:  Jordany R Maignan; Cynthia L Lichorowic; James Giarrusso; Lynn D Blake; Debora Casandra; Tina S Mutka; Alexis N LaCrue; Jeremy N Burrows; Paul A Willis; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2016-07-12       Impact factor: 8.039

10.  Computational Study of Quinolone Derivatives to Improve their Therapeutic Index as Anti-malaria Agents: QSAR and QSTR.

Authors:  Maryam Iman; Asghar Davood; Ali Khamesipour
Journal:  Iran J Pharm Res       Date:  2015       Impact factor: 1.696
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