A3- and A2B-fluorocorroles: synthesis, X-ray characterization and antiviral activity evaluation against human cytomegalovirus infection

Twenty-nine fluorinated corroles were prepared, spectroscopically characterized, and studied for their antiviral activity against human cytomegalovirus infection. Six corroles were also fully characterized by X-ray crystallography giving insights on their geometrical features. The halogenated corrol...

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Bibliographic Details
Published in:MedChemComm 2020-07, Vol.11 (7), p.783-801
Main Authors: Kappler-Gratias, Sandrine, Bucher, Léo, Desbois, Nicolas, Rousselin, Yoann, Bystricky, Kerstin, Gros, Claude P, Gallardo, Franck
Format: Article
Language:English
Subjects:
Antiviral activity
Chemistry
Combinatorial analysis
Crystallography
Cytomegalovirus
Fluorine
Ganciclovir
High-performance liquid chromatography
Infections
Liquid chromatography
NMR
Nuclear magnetic resonance
Selectivity
X-ray crystallography
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Summary:Twenty-nine fluorinated corroles were prepared, spectroscopically characterized, and studied for their antiviral activity against human cytomegalovirus infection. Six corroles were also fully characterized by X-ray crystallography giving insights on their geometrical features. The halogenated corroles reported herein exhibit significantly improved antiviral activity over their non-halogenated counterparts and over nitro-corrole analogs previously reported. Full activity of thirteen A3-corroles is achieved with four fluorine atoms present on the meso-phenyl ring reaching a selectivity index above 300. The maximum activity is achieved for A2B-corroles with selectivity indexes above 400. We thus demonstrate that the fluorocorrole is a highly potent platform to synthesize a new generation of anti hCMV molecules.
ISSN:2040-2503
2040-2511
2632-8682
DOI:10.1039/d0md00127a