Synthesis, characterization, and anti-melanoma activity of tetra-O-substituted analogs of nordihydroguaiaretic acid

Ross O. Meyers, Joshua D. Lambert, Nicole Hajicek, Alan Pourpak, John A. Kalaitzis, Robert T Dorr

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Synthesis of seven semi-synthetic analogs of NDGA is described. An approach to NDGA derivatization is described in which the ortho-phenolic groups are tethered together by one atom, forming a 5-membered heterocyclic ring. The analogs were evaluated for cytotoxicity in four cancer cell lines and compared to NDGA and tetra-O-methyl-NDGA (M4N) (1a). NDGA bis-cyclic sulfate (2a), NDGA bis-cyclic carbonate (2b), and methylenedioxyphenyl-NDGA (2d) and NDGA tetra acetate (1b) showed anti-cancer activity in vitro. Two compounds, (1b) and (2b), were evaluated for anticancer activity in a mouse xenograft model of human melanoma and showed dose-dependent activity.

Original languageEnglish (US)
Pages (from-to)4752-4755
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number16
DOIs
StatePublished - Aug 15 2009

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Masoprocol
Carbonates
Cytotoxicity
Heterografts
Sulfates
Melanoma
Acetates
Cells
Atoms
Neoplasms
Cell Line
terameprocol
In Vitro Techniques

Keywords

  • Analogs
  • Cancer
  • Melanoma
  • NDGA
  • Nordihydroguaiaretic acid

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Synthesis, characterization, and anti-melanoma activity of tetra-O-substituted analogs of nordihydroguaiaretic acid. / Meyers, Ross O.; Lambert, Joshua D.; Hajicek, Nicole; Pourpak, Alan; Kalaitzis, John A.; Dorr, Robert T.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 16, 15.08.2009, p. 4752-4755.

Research output: Contribution to journalArticle

Meyers, Ross O. ; Lambert, Joshua D. ; Hajicek, Nicole ; Pourpak, Alan ; Kalaitzis, John A. ; Dorr, Robert T. / Synthesis, characterization, and anti-melanoma activity of tetra-O-substituted analogs of nordihydroguaiaretic acid. In: Bioorganic and Medicinal Chemistry Letters. 2009 ; Vol. 19, No. 16. pp. 4752-4755.
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AU - Kalaitzis, John A.

AU - Dorr, Robert T

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