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

Ekengard, Erik LU ; Bergare, Ida; Doverbratt, Isa LU ; Monari, Magda; Gordhan, Bhavna; Kana, Bavesh; de Kock, Carmen; Smith, Peter J; Nordlander, Ebbe LU and Hansson, Josefine (2017) In Journal of the Mexican Chemical Society 61(2). p.158-166
Abstract

The synthesis and characterization of N-(2-((7-chloroquino-lin-4-yl)amino)ethyl)pyrazine-2-carboxamide (L), an aminoquinoline – pyrazinamide hybrid, and the complexes (N-(2-((7-chloroquino-lin-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... (More)

The synthesis and characterization of N-(2-((7-chloroquino-lin-4-yl)amino)ethyl)pyrazine-2-carboxamide (L), an aminoquinoline – pyrazinamide hybrid, and the complexes (N-(2-((7-chloroquino-lin-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)pyr-azine-2-carboxamide)(cyclopentadienyl)chloro-iridium chloride are presented.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Chloroquine, Half-sandwich, Malaria, Organometallic, Pyrazinamide, Tuberculosis
in
Journal of the Mexican Chemical Society
volume
61
issue
2
pages
9 pages
publisher
Mexican Chemical Society
external identifiers
  • scopus:85026772040
ISSN
1870-249X
language
English
LU publication?
yes
id
35421630-063b-4912-8fec-acc169c403fb
date added to LUP
2017-09-01 10:26:08
date last changed
2017-09-01 10:26:08
@article{35421630-063b-4912-8fec-acc169c403fb,
  abstract     = {<p>The synthesis and characterization of N-(2-((7-chloroquino-lin-4-yl)amino)ethyl)pyrazine-2-carboxamide (L), an aminoquinoline – pyrazinamide hybrid, and the complexes (N-(2-((7-chloroquino-lin-4-yl)amino)ethyl)pyrazine-2-carboxamide)(cyclopentadienyl) chlorido-rhodium or iridium hexafluorophosphate ([M(L)(Cp*)Cl] PF<sub>6</sub>; 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)pyr-azine-2-carboxamide)(cyclopentadienyl)chloro-iridium chloride are presented.</p>},
  author       = {Ekengard, Erik and Bergare, Ida and Doverbratt, Isa and Monari, Magda and Gordhan, Bhavna and Kana, Bavesh and de Kock, Carmen and Smith, Peter J and Nordlander, Ebbe and Hansson, Josefine },
  issn         = {1870-249X},
  keyword      = {Chloroquine,Half-sandwich,Malaria,Organometallic,Pyrazinamide,Tuberculosis},
  language     = {eng},
  month        = {04},
  number       = {2},
  pages        = {158--166},
  publisher    = {Mexican Chemical Society},
  series       = {Journal of the Mexican Chemical Society},
  title        = {A pyrazine amide – 4-aminoquinoline hybrid and its rhodium and iridium pentamethylcyclopentadienyl complexes; evaluation of anti-mycobacterial and anti-plasmodial activities},
  volume       = {61},
  year         = {2017},
}