Literature DB >> 20568776

Synthesis and evaluation of alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) as antimalarials.

Thomas Verbrugghen1, Paul Cos, Louis Maes, Serge Van Calenbergh.   

Abstract

Three alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) have been synthesized from diethyl but-3-enylphosphonate using a previously described method for the alpha-halogenation of alkylphosphonates. These analogues were evaluated for antimalarial potential in vitro against Plasmodium falciparum and in vivo in the P. berghei mouse model. All three analogues showed higher in vitro and/or in vivo potency than the reference compounds.

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Year:  2010        PMID： 20568776     DOI： 10.1021/jm100211e

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


  7 in total

1.  Structure-guided design and biosynthesis of a novel FR-900098 analogue as a potent Plasmodium falciparum 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr) inhibitor.

Authors:  Ryan E Cobb; Brian Bae; Zhi Li; Matthew A DeSieno; Satish K Nair; Huimin Zhao
Journal:  Chem Commun (Camb)       Date:  2015-02-14       Impact factor: 6.222

2.  Structure-Activity Relationships of the MEPicides: N-Acyl and O-Linked Analogs of FR900098 as Inhibitors of Dxr from Mycobacterium tuberculosis and Yersinia pestis.

Authors:  Géraldine San Jose; Emily R Jackson; Amanda Haymond; Chinchu Johny; Rachel L Edwards; Xu Wang; R Carl Brothers; Emma K Edelstein; Audrey R Odom; Helena I Boshoff; Robin D Couch; Cynthia S Dowd
Journal:  ACS Infect Dis       Date:  2016-10-12       Impact factor: 5.084

3.  Design of Potential Bisubstrate Inhibitors against Mycobacterium tuberculosis (Mtb) 1-Deoxy-D-Xylulose 5-Phosphate Reductoisomerase (Dxr)-Evidence of a Novel Binding Mode.

Authors:  Géraldine San Jose; Emily R Jackson; Eugene Uh; Chinchu Johny; Amanda Haymond; Lindsay Lundberg; Chelsea Pinkham; Kylene Kehn-Hall; Helena I Boshoff; Robin D Couch; Cynthia S Dowd
Journal:  Medchemcomm       Date:  2013-07-01       Impact factor: 3.597

4.  Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents.

Authors:  Charlotte Courtens; Martijn Risseeuw; Guy Caljon; Paul Cos; Serge Van Calenbergh
Journal:  ACS Med Chem Lett       Date:  2018-09-11       Impact factor: 4.345

5.  Molecular basis of fosmidomycin's action on the human malaria parasite Plasmodium falciparum.

Authors:  Tomonobu Umeda; Nobutada Tanaka; Yoshio Kusakabe; Masayuki Nakanishi; Yukio Kitade; Kazuo T Nakamura
Journal:  Sci Rep       Date:  2011-06-14       Impact factor: 4.379

6.  Synthesis of functionalized cinnamaldehyde derivatives by an oxidative Heck reaction and their use as starting materials for preparation of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors.

Authors:  Anneli Nordqvist; Christofer Björkelid; Mounir Andaloussi; Anna M Jansson; Sherry L Mowbray; Anders Karlén; Mats Larhed
Journal:  J Org Chem       Date:  2011-10-07       Impact factor: 4.354

7.  MEPicides: potent antimalarial prodrugs targeting isoprenoid biosynthesis.

Authors:  Rachel L Edwards; Robert C Brothers; Xu Wang; Maxim I Maron; Peter D Ziniel; Patricia S Tsang; Thomas E Kraft; Paul W Hruz; Kim C Williamson; Cynthia S Dowd; Audrey R Odom John
Journal:  Sci Rep       Date:  2017-08-21       Impact factor: 4.379
  7 in total

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