Synthesis and antitumor activity of combretastatin D-4

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

doi:10.3987/COM-07-11221

Synthesis and antitumor activity of combretastatin D-4

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

Department of Biosciences and Informatics

Research output: Contribution to journal › Article

6 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 language	English
Pages (from-to)	291-296
Number of pages	6
Journal	Heterocycles
Volume	75
Issue number	2
DOIs	https://doi.org/10.3987/COM-07-11221
Publication status	Published - 2008 Feb 1

Keywords

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

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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author = "Kanako Uno and Takamasa Tanabe and Takahisa Ogamino and Ryoko Okada and Masaya Imoto and Shigeru Nishiyama",

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T1 - Synthesis and antitumor activity of combretastatin D-4

AU - Uno, Kanako

AU - Tanabe, Takamasa

AU - Ogamino, Takahisa

AU - Okada, Ryoko

AU - Imoto, Masaya

AU - Nishiyama, Shigeru

PY - 2008/2/1

Y1 - 2008/2/1

N2 - 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.

AB - 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.

KW - Anodic Oxidation

KW - Combretastatin D-4

KW - Cyclic Diarylheptanoid

KW - Getonia floribunda

KW - One-Electron Oxidation

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