Structure-antitubulin activity relationships in steganacin congeners and analogs. Inhibition of tubulin polymerization in vitro by (.+-.)-isodeoxypodophyllotoxin

Journal of Medicinal Chemistry
1980.0

Abstract

A new series of 23 synthetic analogues of the naturally occurring antitumor lignan steganacin was tested for the inhibition of microtubule assembly in vitro. Interestingly, (+/-)-isopicrostegane (I50 = 5 microM) was found to be almost as active as (+/-)-steganacin(I50 = 3.5 microM). On the other hand, racemic isodeoxypodophyllotoxin has an inhibiting activity of microtubule assembly comparable to that of (-)-podophyllotoxin, whereas (-)-isodeoxypodophyllotoxin is totally inactive.

Knowledge Graph

Similar Paper

Structure-antitubulin activity relationships in steganacin congeners and analogs. Inhibition of tubulin polymerization in vitro by (.+-.)-isodeoxypodophyllotoxin
Journal of Medicinal Chemistry 1980.0
Synthesis and biological evaluation of podophyllotoxin congeners as tubulin polymerization inhibitors
Bioorganic & Medicinal Chemistry 2014.0
Stereoselective reactions. XVII. Absolute structure-cytotoxic activity relationships of steganacin congeners and analogs
Journal of Medicinal Chemistry 1991.0
Novel Antimitotic Dibenzocyclo-Octadiene Lignan Constituents of the Stem Bark of Steganotaenia araliacea
Journal of Natural Products 1993.0
Relationships between the structure of taxol analogs and their antimitotic activity
Journal of Medicinal Chemistry 1991.0
Synthesis and biological evaluation of a series of podophyllotoxins derivatives as a class of potent antitubulin agents
Bioorganic & Medicinal Chemistry 2012.0
Tubulysin analogs incorporating desmethyl and dimethyl tubuphenylalanine derivatives
Bioorganic & Medicinal Chemistry Letters 2008.0
Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1,5-disubstituted 1,2,3-triazole via ruthenium-catalyzed click chemistry
Bioorganic & Medicinal Chemistry 2007.0
Synthesis of 4β-N-polyaromatic substituted podophyllotoxins: DNA topoisomerase inhibition, anticancer and apoptosis-inducing activities
Bioorganic & Medicinal Chemistry 2010.0
Podophyllotoxin analogues active versus Trypanosoma brucei
Bioorganic & Medicinal Chemistry Letters 2010.0