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The solubility and stability of heterocyclic chalcones compared with trans ‐chalcone
Author(s) -
Sweeting Stephen G.,
Hall Charlie L.,
Potticary Jason,
Pridmore Natalie E.,
Warren Stephen D.,
Cremeens Matthew E.,
D'Ambruoso Gemma D.,
Matsumoto Masaomi,
Hall Simon R.
Publication year - 2020
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520619015907
Subject(s) - chalcone , solubility , melting point , chemistry , antifungal , thiophene , intermolecular force , ring (chemistry) , medicinal chemistry , stereochemistry , organic chemistry , molecule , medicine , dermatology
Heterocyclic chalcones are a recently explored subgroup of chalcones that have sparked interest due to their significant antibacterial and antifungal capabilities. Herein, the structure and solubility of two such compounds, ( E )‐1‐(1 H ‐pyrrol‐2‐yl)‐3‐(thiophen‐2‐yl)prop‐2‐en‐1‐one and ( E )‐3‐phenyl‐1‐(1 H ‐pyrrol‐2‐yl)prop‐2‐en‐1‐one, are assessed. Single crystals of ( E )‐1‐(1 H ‐pyrrol‐2‐yl)‐3‐(thiophen‐2‐yl)prop‐2‐en‐1‐one were grown, allowing structural comparisons between the heterocyclic chalcones and (2 E )‐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 to have higher melting points than trans ‐chalcone, probably due to their stronger intermolecular interactions arising from the functionalized rings. Interestingly, however, it was found that the addition of the thiophene ring in ( E )‐1‐(1 H ‐pyrrol‐2‐yl)‐3‐(thiophen‐2‐yl)prop‐2‐en‐1‐one increased both the melting point and solubility of the sample compared with ( E )‐3‐phenyl‐1‐(1 H ‐pyrrol‐2‐yl)prop‐2‐en‐1‐one. This observation may be key for the future crystal engineering of heterocyclic chalcones for pharmaceutical applications.