Cyrhetrenyl and ferrocenyl 1,3,4-thiadiazole derivatives: Synthesis, characterization, crystal structures and in vitro antitubercular activity

Cristóbal Quintana, A. Hugo Klahn, Vania Artigas, Mauricio Fuentealba, Christophe Biot, Iman Halloum, Laurent Kremer, Rodrigo Arancibia

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

A new series of cyrhetrenyl and ferrocenyl 1,3,4-thiadiazoles (TDZs) were designed, synthesized and characterized. The condensation-cyclization reaction of organometallic-cyanide with the corresponding thiosemicarbazide produces the ferrocenyl-TDZs (3a-c) and cyrhetrenyl analogues (4ac). The structures of all products were inferred from their elemental analysis, 1H and 13C NMR spectra and MS. The molecular structures of 3b and 4b were confirmed using X-ray crystallography. The electronic effects of cyrhetrenyl (4a-c) and ferrocenyl (3a-c) bound directly to the thiadiazole ring have been correlated with the chemical shift of the exocyclic amine proton and 13C shift of the carbon at the 5-position. The X-ray crystal structure of 3b and 4b indicates that the rhenium compound 4b possesses a more extensive conjugated π-system. The activity of the new organometallic-TDZs was evaluated in vitro against Mycobacterium tuberculosis. The incorporation of any organometallic fragment into the thiadiazole skeleton showed a comparable but lower antitubercular activity than isoniazid.

Original languageEnglish
Pages (from-to)48-50
Number of pages3
JournalInorganic Chemistry Communications
Volume55
DOIs
StatePublished - May 2015
Externally publishedYes

Keywords

  • 1,3,4-Thiadiazole
  • Anti-Mycobacterium tuberculosis
  • Cyrhetrene
  • Ferrocene
  • Tuberculosis

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