2. Academic Validation
  3. Synthesis, antibiofilm activity and molecular docking of N-acylhomoserine lactones containing cinammic moieties

Synthesis, antibiofilm activity and molecular docking of N-acylhomoserine lactones containing cinammic moieties

  • Bioorg Med Chem Lett. 2023 Dec 13:98:129592. doi: 10.1016/j.bmcl.2023.129592.
Ángel Ramírez-Trinidad 1,  Ernesto Martínez-Solano 1,  César E Tovar-Roman 1,  Mariana García-Guerrero 2,  José A Rivera-Chávez 2,  Eduardo Hernández-Vázquez 3
Affiliations

Affiliations

  • 1 Department of Organic Chemistry, Chemistry Institute, UNAM. Circuito exterior S.N., Ciudad Universitaria, Coyoacán, México, DF 04510, Mexico.
  • 2 Department of Natural Products, Chemistry Institute, UNAM. Circuito exterior S.N., Ciudad Universitaria, Coyoacán, México, DF 04510, Mexico.
  • 3 Department of Organic Chemistry, Chemistry Institute, UNAM. Circuito exterior S.N., Ciudad Universitaria, Coyoacán, México, DF 04510, Mexico. Electronic address: ehervaz@iquimica.unam.mx.
PMID: 38101651 DOI: 10.1016/j.bmcl.2023.129592
Abstract

We prepared a series of cinnamoyl-containing furanones by an affordable and short synthesis. The nineteen compounds hold a variety of substituents including electron-donating, electron-withdrawing, bulky and meta-substituted phenyls, as well as heterocyclic rings. Compounds showed antibiofilm activity in S. aureus, K. pneumoniae and, more pronounced, against P. aeruginosa. The disruption of quorum sensing (QS) was tested using the violacein test and molecular docking predicted the antagonism of LasR as a plausible mechanism of action. The trimethoxylated and diene derivatives showed the best antibiofilm and anti-QS properties, thus becoming candidates for further modifications.

Keywords

Anti-QS; Antibiofilm; LasR antagonists; N-acylhomoserine lactones.

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