title: D-Glucose-Derived 1,2,4-Trioxepanes: Synthesis, Conformational Study, and Antimalarial Activity.
abstract: New enantiomerically pure 1,2,4-trioxepanes 10a,b/11a,b were synthesized from D-glucose. Their conformational behavior was studied by low-temperature NMR and substantiated by DFT calculations. On evaluation of in vitro antimalarial activity, the adamantyl derivative 11b showed IC50 values in the low micromolar range, particularly against the W2 chloroquine-resistant Plasmodium falciparum strain (IC50 = 0.15 ± 0.12 μM).
authors.affiliation: †Department of Chemistry, Garware Research Centre, Savitribai Phule Pune University (formerly University of Pune), Pune 411 007, India.
authors.forename: D P
authors.initials: DP
authors.lastname: Sonawane
authors.affiliation: ‡Dipartimento di Scienze Farmacologiche e Biomolecolari, Università di Milano, Via Pascal 36, 20133 Milano, Italy.
authors.forename: Y
authors.initials: Y
authors.lastname: Corbett
authors.affiliation: †Department of Chemistry, Garware Research Centre, Savitribai Phule Pune University (formerly University of Pune), Pune 411 007, India.
authors.forename: D D
authors.initials: DD
authors.lastname: Dhavale
authors.affiliation: ‡Dipartimento di Scienze Farmacologiche e Biomolecolari, Università di Milano, Via Pascal 36, 20133 Milano, Italy.
authors.forename: D
authors.initials: D
authors.lastname: Taramelli
authors.affiliation: #Dipartimento di Chimica "Giacomo Ciamician", Alma Mater Studiorum, Università di Bologna, via Selmi, 2, I-40126 Bologna, Italy.
authors.forename: C
authors.initials: C
authors.lastname: Trombini
authors.affiliation: #Dipartimento di Chimica "Giacomo Ciamician", Alma Mater Studiorum, Università di Bologna, via Selmi, 2, I-40126 Bologna, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Quintavalla
authors.affiliation: #Dipartimento di Chimica "Giacomo Ciamician", Alma Mater Studiorum, Università di Bologna, via Selmi, 2, I-40126 Bologna, Italy.
authors.forename: M
authors.initials: M
authors.lastname: Lombardo
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002738:Chloroquine / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D005947:Glucose / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects / Q000235:genetics; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000962:Antimalarials; D010082:Oxepins; D002738:Chloroquine; D005947:Glucose; D000218:Adamantane