| Autor: |
Pettit GR; Cancer Research Institute and Department of Chemistry, Arizona State University, Tempe, Arizona 87287-2404, USA., Lippert JW 3rd, Herald DL |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2000 Nov 03; Vol. 65 (22), pp. 7438-44. |
| DOI: |
10.1021/jo000705j |
| Abstrakt: |
In an attempt to develop biologically active compounds from the inactive trans isomer (3a) of stilbene 1a, after asymmetric dihydroxylation to optically pure (R,R)-diol 8 the unexpected racemic diphenylacetaldehyde (9) was generated via a Pinacol rearrangement. Several derivatives of diphenylacetaldehyde 9 were synthesized (11-15) and reported. Further reaction of aldehyde 9 during desilylation through autoxidative decarbonylation afforded benzophenone 2b, designated hydroxyphenstatin, a potent antitumor and antimitotic agent. Hydroxyphenstatin showed potent inhibition of the tubulin assembly (IC(50) 0.82 microM) and exhibited an ED(50) of 2.5 microg/mL against the P388 lymphocytic leukemia cell line. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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