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Semisynthesis, Characterization, and Biological Evaluation of Fluorinated Analogues of the Spirobisnaphthalene, Diepoxin-η.
Pourhadi, Hadi; El-Elimat, Tamam; Rangel-Grimaldo, Manuel; Graf, Tyler N; Falkinham, Joseph O; Khin, Manead; Burdette, Joanna E; Mirtallo Ezzone, Nathan; Jeyaraj, Jonathan; de Blanco, Esperanza Carcache; Pearce, Cedric J; Oberlies, Nicholas H.
Afiliação
  • Pourhadi H; Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, United States.
  • El-Elimat T; Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, United States.
  • Rangel-Grimaldo M; Department of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, Irbid 22110, Jordan.
  • Graf TN; Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, United States.
  • Falkinham JO; Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, United States.
  • Khin M; Department of Biological Sciences, Virginia Polytechnic and State University, Blacksburg, VA 24061, United States.
  • Burdette JE; Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
  • Mirtallo Ezzone N; Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States.
  • Jeyaraj J; Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Ohio State University, Columbus, Ohio 43210, United States.
  • de Blanco EC; Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Ohio State University, Columbus, Ohio 43210, United States.
  • Pearce CJ; Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Ohio State University, Columbus, Ohio 43210, United States.
  • Oberlies NH; Mycosynthetix, Inc., Hillsborough, NC 27278, United States.
Tetrahedron Lett ; 1342024 Jan 12.
Article em En | MEDLINE | ID: mdl-38328000
ABSTRACT
Diepoxin-η (1) is a cytotoxic fungal metabolite belonging to the spirobisnaphthalene structural class. In this study, four mono fluorinated analogues (2-5) of diepoxin-η (1) were semisynthesized in a single-step by selectively fluorinating the naphthalene moiety with Selectfluor. The structures of 2-5 were elucidated using a set of spectroscopic and spectrometric techniques and were further confirmed by means of TDDFT-ECD and isotropic shielding tensors calculations. Compounds 2-5 showed equipotent cytotoxic activity to 1 when tested against OVCAR3 (ovarian) and MDA-MB-435 (melanoma) cancer cell lines with IC50 values that range from 5.7-8.2 µM.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Tetrahedron Lett Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Estados Unidos
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Tetrahedron Lett Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Estados Unidos