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

Authors

  • Erik Ekengard Lund University
  • Ida Bergare Lund University
  • Josefine Hansson Lund University
  • Isa Doverbratt Lund University
  • Magda Monari Università di Bologna
  • Bhavna Gordhan 1. University of the Witwatersrand 2. National Health Laboratory Service
  • Bavesh Kana 1. University of the Witwatersrand 2. National Health Laboratory Service
  • Carmen de Kock University of Cape Town Medical School
  • Peter J. Smith University of Cape Town Medical School
  • Ebbe Nordlander Lund University

DOI:

https://doi.org/10.29356/jmcs.v61i2.263

Keywords:

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

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.

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Author Biographies

Erik Ekengard, Lund University

Inorganic Chemistry Research Group, Chemical Physics, Department of Chemistry

Ida Bergare, Lund University

Inorganic Chemistry Research Group, Chemical Physics, Department of Chemistry

Josefine Hansson, Lund University

Inorganic Chemistry Research Group, Chemical Physics, Department of Chemistry

Isa Doverbratt, Lund University

Center for Analysis and Synthesis, Department of Chemistry

Magda Monari, Università di Bologna

Dipartimento di Chimica “G. Ciamician”

Bhavna Gordhan, 1. University of the Witwatersrand 2. National Health Laboratory Service

1. DST/NRF Centre of Excellence for Biomedical TB Research, School of Pathology, Faculty of Health Sciences

Bavesh Kana, 1. University of the Witwatersrand 2. National Health Laboratory Service

1. DST/NRF Centre of Excellence for Biomedical TB Research, School of Pathology, Faculty of Health Sciences

Carmen de Kock, University of Cape Town Medical School

Division of Pharmacology, Department of Medicine

Peter J. Smith, University of Cape Town Medical School

Division of Pharmacology, Department of Medicine

Ebbe Nordlander, Lund University

Inorganic Chemistry Research Group, Chemical Physics, Department of Chemistry

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Published

2017-10-12

Issue

Vol. 61 No. 2 (2017): Special Issue dedicated to Prof. Roberto Sánchez-Delgado

Section

Regular Articles

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