Synthesis and antibacterial activities of cadiolides A, B and C and analogues.
The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils.
Normandie Univ, COBRA, UMR 6014 et FR 3038, CNRS, Univ Rouen, INSA Rouen, 1 rue Tesnières, 76821 Mont-Saint-Aignan, Cedex, France.
Agathe
A
Boulangé
Departamento de Farmacología, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot Valencia, Spain.
Javier
J
Parraga
Departamento de Farmacología, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot Valencia, Spain.
Abraham
A
Galán
Departamento de Farmacología, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot Valencia, Spain; Centro de Ecología Química Agrícola-Instituto Agroforestal Mediterraneo, UPV, Campus de Vera, Edificio 6C, 46022 Valencia, Spain.
Nuria
N
Cabedo
Normandie Univ, COBRA, UMR 6014 et FR 3038, CNRS, Univ Rouen, INSA Rouen, 1 rue Tesnières, 76821 Mont-Saint-Aignan, Cedex, France.
Stéphane
S
Leleu
Departamento de Farmacología, Facultad de Medicina, Universidad de Valencia, 46010 Valencia, Spain; Institute of Health Research-INCLIVA, University Clinic Hospital of Valencia, 46010 Valencia, Spain.
Maria Jesus
MJ
Sanz
Departamento de Farmacología, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot Valencia, Spain.
Diego
D
Cortes
Normandie Univ, COBRA, UMR 6014 et FR 3038, CNRS, Univ Rouen, INSA Rouen, 1 rue Tesnières, 76821 Mont-Saint-Aignan, Cedex, France. Electronic address: xavier.franck@insa-rouen.fr.
Xavier
X
Franck
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects / Q000254:growth & development; D006094:Gram-Positive Bacteria / Q000187:drug effects / Q000254:growth & development; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009504:Neutrophils / Q000166:cytology / Q000187:drug effects; D061251:Primary Cell Culture; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; C000599604:cadiolide A; C000599605:cadiolide B; C578395:cadiolide C; D015107:4-Butyrolactone
Antibacterial; Butenolides; Cadiolides; Multicomponent; Natural products