title: Synthesis and antifungal activity of terpenyl-1,4-naphthoquinone and 1,4-anthracenedione derivatives.
abstract: The antifungal evaluation of twenty seven simple and heterocycle-fused prenyl-1,4-naphthoquinones and 1,4-anthracenediones was performed in vitro against human pathogenic yeasts (Candida spp.) and filamentous fungi (Aspergillus spp., Fusarium spp., and Trichophyton spp.). The synthetic strategy used to obtain the quinone derivatives was initially based on the Diels-Alder cycloaddition between myrcene and several p-benzoquinone derivatives, followed by cyclisation of the prenyl side chain in the case of anthracene-1,4-diones. The most promising compounds, displaying MIC values in the low μg/mL range, were those bearing one or two chlorine atoms attached to the quinone ring. Time-kill curves determined for the most potent compounds showed their fungistatic mode of action similar to that of itraconazole.
authors.affiliation: Departamento de Química Farmacéutica, Facultad de Farmacia, CIETUS-IBSAL. Universidad de Salamanca, Campus Miguel de Unamuno, E-37007 Salamanca, Spain. Electronic address: macg@usal.es.
authors.forename: Ma Ángeles
authors.initials: MÁ
authors.lastname: Castro
authors.forename: Ana Ma
authors.initials: AM
authors.lastname: Gamito
authors.forename: Verónica
authors.initials: V
authors.lastname: Tangarife-Castaño
authors.forename: Bibiana
authors.initials: B
authors.lastname: Zapata
authors.forename: José Ma
authors.initials: JM
authors.lastname: Miguel del Corral
authors.forename: Ana C
authors.initials: AC
authors.lastname: Mesa-Arango
authors.forename: Liliana
authors.initials: L
authors.lastname: Betancur-Galvis
authors.forename: Arturo
authors.initials: A
authors.lastname: San Feliciano
mesh_terms: D000818:Animals; D000873:Anthracenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001230:Aspergillus / Q000187:drug effects*; D002175:Candida / Q000187:drug effects*; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D004305:Dose-Response Relationship, Drug; D005670:Fusarium / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014249:Trichophyton / Q000187:drug effects*; D014709:Vero Cells
chemical_list: C587473:1,4-anthracenedione; D000873:Anthracenes; D000935:Antifungal Agents; D009285:Naphthoquinones; C587474:terpenyl-1,4-naphthoquinone
keywords: 1,4-Anthracenediones; AQFXONODKYWQSJ-UHFFFAOYSA-N; AXWNCVPMVLGONY-UHFFFAOYSA-N; Antifungal; BPNWZFPZYMQGFZ-UHFFFAOYSA-N; CGOUQDNKIYPOFC-UHFFFAOYSA-N; Diels–Alder; GEKMMIKMBVJKCC-UHFFFAOYSA-N; GINLNPRDXAJVNL-UHFFFAOYSA-N; HKTXIZYRBAIWHV-UHFFFAOYSA-N; HUQHMCMEOPOZRD-UHFFFAOYSA-N; IJBZBRBJFNDEBL-UHFFFAOYSA-N; IPTGZNXCTVYNKX-UHFFFAOYSA-N; JCDZBDQVNWPSRQ-UHFFFAOYSA-N; NIFYABLHXCNJIA-UHFFFAOYSA-N; NJVQHLGPVDDQSQ-UHFFFAOYSA-N; Prenyl-1,4-naphthoquinones; QRPFJXKTWHPOKX-UHFFFAOYSA-N; RWFRBRHGMAIPIU-UHFFFAOYSA-N; SLHDHXUIYBDREX-UHFFFAOYSA-N; Time-kill curves; UWAOFISELDUZCC-UHFFFAOYSA-N; VYSDUEXKBZEHHE-UHFFFAOYSA-N; WCMVWAWTBUMGFZ-UHFFFAOYSA-N; YMQDIVBKUCNLKA-UHFFFAOYSA-N; ZIGZDQSXZLVQGI-UHFFFAOYSA-N