Tubulin inhibitors. Synthesis and biological activity of HTI-286 analogs with B-segment heterosubstituents

Bioorganic & Medicinal Chemistry Letters
2004.0

Abstract

Modifications of the B-segment of HTI-286 (2) produced a class of analogs incorporating heteroatom-substituents. The structure-activity relationship was studied. Analogs bearing methylsulfide and fluoride groups exhibited potency comparable to that of the parent compound HTI-286 and to paclitaxel in cytotoxicity assays against KB-3-1 cell lines. These analogs were more potent than paclitaxel against P-glycoprotein expressing KB-8-5 and KB-V1 cell lines. Several analogs showed strong inhibition of tubulin polymerization.

Knowledge Graph

Similar Paper

Tubulin inhibitors. Synthesis and biological activity of HTI-286 analogs with B-segment heterosubstituents
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and Biological Activity of Analogues of the Antimicrotubule AgentN,β,β-Trimethyl-<scp>l</scp>-phenylalanyl-N-[(1S,2E)-3-carboxy-1-isopropylbut-2-enyl]-N<sup>1</sup>,3-dimethyl-<scp>l</scp>-valinamide (HTI-286)
Journal of Medicinal Chemistry 2004.0
Tubulysin analogs incorporating desmethyl and dimethyl tubuphenylalanine derivatives
Bioorganic &amp; Medicinal Chemistry Letters 2008.0
Structure–activity relationships study at the 3′-N position of paclitaxel. part 2: synthesis and biological evaluation of 3′-N-thiourea- and 3′-N-thiocarbamate-bearing paclitaxel analogues
Bioorganic &amp; Medicinal Chemistry Letters 2000.0
Butitaxel Analogues:  Synthesis and Structure−Activity Relationships
Journal of Medicinal Chemistry 1997.0
Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors
European Journal of Medicinal Chemistry 2016.0
Synthesis and biological evaluation of a novel class of isatin analogs as dual inhibitors of tubulin polymerization and Akt pathway
Bioorganic &amp; Medicinal Chemistry 2011.0
Discovery of Novel Benzimidazole and Indazole Analogues as Tubulin Polymerization Inhibitors with Potent Anticancer Activities
Journal of Medicinal Chemistry 2021.0
Synthesis, biological activity and tubulin binding poses of 1-deoxy-9-(R)-dihydrotaxane analogs
Bioorganic &amp; Medicinal Chemistry Letters 2009.0