Colchicine Models: Synthesis and Binding to Tubulin of Tertamethoxybiphenyls
- 10 August 1988
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 71 (5) , 1199-1209
- https://doi.org/10.1002/hlca.19880710531
Abstract
Syntheis of tetramethoxybiphenyl 21 was accomplished from 4‐phenylcylohexane‐1,3‐dione 13 by aromatization to biphenyl 19 and reductive removal of the phenolic OH group as phenyltetrazolyl ether. Tertramethoxybiphenyls 34 and 40 were obtained from 4‐phenylcyclohexenone 26 via ester 27. The tetramethoxybiphenyls 21, 34, and 40, and analogs 28, 29, and 31 were evaluated for antitubulin activity and as antimitotic agents with L1210 murine leukemia cells. Compounds 31 and 34 had significant effects on the in‐vitro polymerization of tubulin. Compound 31 was the most cytotoxic of the six new biphenyls studied (IC50 for cell growth, 0.6M) and caused the accumulation of cells in metaphase arrest.This publication has 18 references indexed in Scilit:
- The importance of the phenyl‐tropolone ‘aS’ configuration in colchicine's binding to tubulinFEBS Letters, 1988
- A novel synthesis of colchicide and analogs from thiocolchicine and congeners: reevaluation of colchicide as a potential antitumor agentJournal of Medicinal Chemistry, 1987
- A Novel Synthetic Approach to BiphenylsSynthesis, 1987
- Aromatization of 1‐Benzyltetrahydroisoquinolines: Racemization of (−)‐(S)‐(N‐nor)‐ReticulineHelvetica Chimica Acta, 1981
- A Novel Synthesis of Aporphines via 3‐PhenylphenethylaminesHelvetica Chimica Acta, 1979
- A simple and practical synthesis of olivetolThe Journal of Organic Chemistry, 1977
- Direct and Sequential Removal of Phenolic Oxygen Functions in S-(+)-Bulbocapnine, S-(+)-Boldine and R-(-)-ApomorphineHETEROCYCLES, 1977
- The Replacement of Phenolic Hydroxyl Groups by HydrogenJournal of the American Chemical Society, 1966
- 261. Eine neue Synthese von 3, 5, 4′, 5′‐Tetramethoxydiphensäure, einem Abbauprodukt des Alkaloids ProtostephaninHelvetica Chimica Acta, 1966
- Syntheses of Aucuparin and Methoxyaucuparin.Acta Chemica Scandinavica, 1963