The Solubility and Stability of Heterocyclic Chalcones Compared to Trans-chalcone

Stephen Sweeting, Charlie Hall, Jason Potticary, Natalie E Pridmore, Stephen D Warren, Matthew E Cremeens, Gemma D D'Ambruoso, Masaomi Matsumoto, Simon R Hall

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Abstract

Heterocyclic chalcones are a recently explored subgroup of chalcones that have sparked interest due to their significant antibacterial and antifungal capabilities. Herein, we assess the structure and solubility of two such compounds, (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one and (E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one. Single crystals of (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one were grown, allowing structural comparisons between the heterocyclic chalcones and (2E)-1,3-diphenylprop-2-en-1-one, trivially known as trans-chalcone. The two heterocyclic chalcones were found to be less soluble in all solvents tested and have higher melting points than trans-chalcone, likely due to their stronger intermolecular interactions arising from their heterocyclic nature. Interestingly, however, it was found that the addition of the thiophene ring in (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one increased both the melting point and solubility of the sample compared to (E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one. This observation may be key for the future crystal engineering of heterocyclic chalcones for pharmaceutical applications.
Original languageEnglish
Pages (from-to)13-17
Number of pages4
JournalActa Crystallographica Section B
VolumeB76
Issue number1
DOIs
Publication statusPublished - 1 Feb 2020

Keywords

  • crystal structure
  • heterocyclic chalcones
  • solubility
  • thermal stability
  • intermolecular interactions
  • chalcones
  • crystals

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