title: Synthesis, molecular modeling and biological evaluation of two new chicoric acid analogs.
abstract: Two conformationally constrained compounds similar to chicoric acid but lacking the catechol and carboxyl groups were prepared. In these analogues, the single bond between the two caffeoyl fragments has been replaced with a chiral oxirane ring and both aromatic residues modified protecting completely or partially the catechol moiety as methyl ether. Preliminary molecular modelling studies carried out on the two analogues showed interactions near the active site of HIV integrase; however, in comparison with raltegravir, the biological evaluation confirmed that CAA-1 and CAA-2 were unable to inhibit infection at lower concentration.
authors.affiliation: a CNR-IBPM Department of Chemistry , "Sapienza" Universy of Rome , Rome , Italy.
authors.forename: Giuliana
authors.initials: G
authors.lastname: Righi
authors.affiliation: b Department of Chemistry and IMC-CNR , "Sapienza" Universy of Rome , Roma , Italy.
authors.forename: Romina
authors.initials: R
authors.lastname: Pelagalli
authors.affiliation: b Department of Chemistry and IMC-CNR , "Sapienza" Universy of Rome , Roma , Italy.
authors.forename: Valerio
authors.initials: V
authors.lastname: Isoni
authors.affiliation: b Department of Chemistry and IMC-CNR , "Sapienza" Universy of Rome , Roma , Italy.
authors.forename: Ilaria
authors.initials: I
authors.lastname: Tirotta
authors.affiliation: c CNR-ICB UOS Sassari , Sassari , Italy.
authors.forename: Roberto
authors.initials: R
authors.lastname: Dallocchio
authors.affiliation: c CNR-ICB UOS Sassari , Sassari , Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Dessì
authors.affiliation: d Department of System Medicine , "Tor Vergata" University , Rome , Italy.
authors.forename: Beatrice
authors.initials: B
authors.lastname: Macchi
authors.affiliation: d Department of System Medicine , "Tor Vergata" University , Rome , Italy.
authors.forename: Caterina
authors.initials: C
authors.lastname: Frezza
authors.affiliation: b Department of Chemistry and IMC-CNR , "Sapienza" Universy of Rome , Roma , Italy.
authors.forename: Ilaria
authors.initials: I
authors.lastname: Rossetti
authors.affiliation: a CNR-IBPM Department of Chemistry , "Sapienza" Universy of Rome , Rome , Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Bovicelli
mesh_terms: D002109:Caffeic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019428:HIV Integrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D013386:Succinates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D002109:Caffeic Acids; D019428:HIV Integrase Inhibitors; D013386:Succinates; C100435:chicoric acid
keywords: HIV integrase; analogues; chicoric acid; inhibitors