A pyrazine amide – 4-aminoquinoline hybrid and its rhodium and iridium pentamethylcyclopentadienyl complexes; evaluation of anti-mycobacterial and anti-plasmodial activities

Erik Ekengard, Ida Bergare, Josefine Hansson, Isa Doverbratt, Magda Monari, Bhavna Gordhan, Bavesh Kana, Carmen de Kock, Peter J. Smith, Ebbe Nordlander

Abstract


The synthesis and characterization of N-(2-((7-chloroquinolin-4-yl)amino)ethyl)pyrazine-2-carboxamide (L), an aminoquinoline – pyrazinamide hybrid, and the complexes (N-(2-((7-chloroquinolin-4-yl)amino)ethyl)pyrazine-2-carboxamide)(cyclopentadienyl) chlorido-rhodium or iridium hexafluorophosphate ([M(L)(Cp*)Cl] PF6; M = Rh, Ir) and the corresponding chlorido salts ([M(L)(Cp*) Cl]Cl; M = Rh, Ir) are described. The ligand and the hexafluorophosphate salts of the metal complexes have been evaluated for anti-plasmodial and anti-mycobacterial activity. The rhodium and the iridium complexes were significantly more active against M. tuberculosis than the free ligand. The crystallographically determined molecular structures of complexes (N-(2-((7-chloroquinolin-4-yl)amino)ethyl)pyrazine-2-carboxamide)(cyclopentadienyl)chlororhodium hexafluoro-phosphate and (N-(2-((7-chloroquinolin-4-yl)amino)ethyl)pyrazine-2-carboxamide)(cyclopentadienyl)chloro-iridium chloride are presented.

Keywords


Malaria; tuberculosis; half-sandwich; organometallic; chloroquine; pyrazinamide

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Copyright (c) 2017 Erik Ekengard, Ida Bergare, Josefine Hansson, Isa Doverbratt, Magda Monari, Bhavna Gordhan, Bavesh Kana, Carmen de Kock, Peter J. Smith, Ebbe Nordlander

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