Synthesis and antitumor activity of combretastatin D-4

Kanako Uno, Takamasa Tanabe, Takahisa Ogamino, Ryoko Okada, Masaya Imoto, Shigeru Nishiyama

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Combretastatin D-4 1 was synthesized using electrochemical dimerization of phenols as the key step. Anodic oxidation of bromochloro-phenol 7 provided the corresponding diaryl ether 8. Manipulation of the two hydroxyl groups differenciated, provided the seco-acid, which on Mitsunobu reaction gave the target molecule. Its biological assay showed new potent inhibitory activity against cellular proliferation of human HT-29 colon carcinoma cells.

Original languageEnglish
Pages (from-to)291-296
Number of pages6
JournalHeterocycles
Volume75
Issue number2
DOIs
Publication statusPublished - 2008 Feb 1

Fingerprint

Dimerization
Phenols
Anodic oxidation
Phenol
Biological Assay
Hydroxyl Radical
Ether
Assays
Colon
Cells
Cell Proliferation
Carcinoma
Molecules
Acids
combretastatin

Keywords

  • Anodic Oxidation
  • Combretastatin D-4
  • Cyclic Diarylheptanoid
  • Getonia floribunda
  • One-Electron Oxidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Uno, K., Tanabe, T., Ogamino, T., Okada, R., Imoto, M., & Nishiyama, S. (2008). Synthesis and antitumor activity of combretastatin D-4. Heterocycles, 75(2), 291-296. https://doi.org/10.3987/COM-07-11221

Synthesis and antitumor activity of combretastatin D-4. / Uno, Kanako; Tanabe, Takamasa; Ogamino, Takahisa; Okada, Ryoko; Imoto, Masaya; Nishiyama, Shigeru.

In: Heterocycles, Vol. 75, No. 2, 01.02.2008, p. 291-296.

Research output: Contribution to journalArticle

Uno, K, Tanabe, T, Ogamino, T, Okada, R, Imoto, M & Nishiyama, S 2008, 'Synthesis and antitumor activity of combretastatin D-4', Heterocycles, vol. 75, no. 2, pp. 291-296. https://doi.org/10.3987/COM-07-11221
Uno K, Tanabe T, Ogamino T, Okada R, Imoto M, Nishiyama S. Synthesis and antitumor activity of combretastatin D-4. Heterocycles. 2008 Feb 1;75(2):291-296. https://doi.org/10.3987/COM-07-11221
Uno, Kanako ; Tanabe, Takamasa ; Ogamino, Takahisa ; Okada, Ryoko ; Imoto, Masaya ; Nishiyama, Shigeru. / Synthesis and antitumor activity of combretastatin D-4. In: Heterocycles. 2008 ; Vol. 75, No. 2. pp. 291-296.
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