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Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on leishmania major growth and trypanosoma brucei trypanothione reductase

A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being co...

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Main Authors: Marcu, Ana (Author) , Schurigt, Uta (Author) , Müller, Klaus (Author) , Moll, Heidrun (Author) , Krauth-Siegel, Renate (Author) , Prinz, Helge (Author)
Format: Article (Journal)
Language:English
Published: 27 January 2016
In: European journal of medicinal chemistry
Year: 2015, Volume: 108, Pages: 436-443
ISSN:1768-3254
DOI:10.1016/j.ejmech.2015.11.023
Online Access:Verlag, lizenzpflichtig, Volltext: http://dx.doi.org/10.1016/j.ejmech.2015.11.023
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Author Notes:Ana Marcu, Uta Schurigt, Klaus Müller, Heidrun Moll, R. Luise Krauth-Siegel, Helge Prinz

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520 |a A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being comparable or superior to those of the reference antiprotozoal drugs. Furthermore, we explored the structure-activity relationships of N-10 haloacetamides that influence the potency of such analogs toward inhibition of L. major promastigote growth in vitro. With respect to the mechanism of action, selected compounds were evaluated for time-dependent inactivation of Trypanosoma brucei trypanothione reductase. Our results are indicative of a covalent interaction which could account for potent antiprotozoal activities. 
534 |c 2015 
650 4 |a Acetamides 
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650 4 |a Enzyme Inhibitors 
650 4 |a Leishmania major 
650 4 |a Molecular Structure 
650 4 |a NADH, NADPH Oxidoreductases 
650 4 |a Oxazines 
650 4 |a Parasitic Sensitivity Tests 
650 4 |a Phenothiazines 
650 4 |a Phenoxazines 
650 4 |a Structure-Activity Relationship 
650 4 |a Trypanosoma brucei brucei 
650 4 |a Trypanothione reductase 
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