title: Preparative chiral separation and absolute configuration of the synthetic pterocarpanquinone LQB-118.
abstract: The racemic pterocarpanquinone LQB-118 is active, in mice and hamsters, against tegumentary and visceral leishmaniasis. This compound also presents antiinflammatory and antineoplastic activity in mice. The low level of toxicity observed in these studies makes LQB-118 a promising drug candidate. In order to conduct further biological testing to investigate enantioselectivity in the above-mentioned activities, a multimilligram amount of each enantiomer of LQB-118 was produced. Furthermore, vibrational circular dichroism (VCD) and Density Functional Theory (DFT) calculations were used to determine unambiguously their absolute configurations. The comparison of experimental and calculated VCD data led to the assignment of (-)-LQB-118 as 7aR,12aR and, consequently, (+)-LQB-118 as 7aS12aS.
authors.affiliation: Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, Brazil.
authors.forename: Gabriel S
authors.initials: GS
authors.lastname: Scatena
authors.affiliation: Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, Brazil.
authors.forename: Neila M
authors.initials: NM
authors.lastname: Cassiano
authors.affiliation: Federal University of Rio de Janeiro - UFRJ, Macaé, Brazil.
authors.forename: Chaquip D
authors.initials: CD
authors.lastname: Netto
authors.affiliation: Federal University of Rio de Janeiro - UFRJ, Rio de Janeiro, Brazil.
authors.forename: Paulo R R
authors.initials: PRR
authors.lastname: Costa
authors.affiliation: Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, Brazil.
authors.forename: Quezia B
authors.initials: QB
authors.lastname: Cass
authors.affiliation: Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, Brazil.
authors.forename: João M
authors.initials: JM
authors.lastname: Batista
mesh_terms: D002942:Circular Dichroism; D008958:Models, Molecular; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000737:chemistry* / Q000302:isolation & purification*; D036343:Pterocarpans / Q000737:chemistry* / Q000302:isolation & purification*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C569361:LQB 118; D009285:Naphthoquinones; D036343:Pterocarpans; D012997:Solvents
keywords: DFT; IR; VCD; conformational analysis; polysaccharide-based column