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 | |
| Publication status | Published - 2008 Feb 1 |
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Keywords
- Anodic Oxidation
- Combretastatin D-4
- Cyclic Diarylheptanoid
- Getonia floribunda
- One-Electron Oxidation
ASJC Scopus subject areas
- Organic Chemistry
Cite this
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 journal › Article
}
TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=43949094858&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=43949094858&partnerID=8YFLogxK
U2 - 10.3987/COM-07-11221
DO - 10.3987/COM-07-11221
M3 - Article
VL - 75
SP - 291
EP - 296
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 2
ER -