330667-09-9Relevant academic research and scientific papers
Synthesis of a 2-aryl-3-aroyl indole salt (OXi8007) resembling combretastatin A-4 with application as a vascular disrupting agent
Hadimani, Mallinath B.,MacDonough, Matthew T.,Ghatak, Anjan,Strecker, Tracy E.,Lopez, Ramona,Sriram, Madhavi,Nguyen, Benson L.,Hall, John J.,Kessler, Raymond J.,Shirali, Anupama R.,Liu, Li,Garner, Charles M.,Pettit, George R.,Hamel, Ernest,Chaplin, David J.,Mason, Ralph P.,Trawick, Mary Lynn,Pinney, Kevin G.
, p. 1668 - 1678 (2013/10/22)
The natural products colchicine and combretastatin A-4 are potent inhibitors of tubulin assembly, and they have inspired the design and synthesis of a large number of small-molecule, potential anticancer agents. The indole-based molecular scaffold is prom
Application of the McMurry coupling reaction in the synthesis of tri- and tetra-arylethylene analogues as potential cancer chemotherapeutic agents
Tanpure, Rajendra P.,Harkrider, Amanda R.,Strecker, Tracy E.,Hamel, Ernest,Trawick, Mary Lynn,Pinney, Kevin G.
experimental part, p. 6993 - 7001 (2009/12/24)
Structural redesign of selected non-steroidal estrogen receptor binding compounds has previously been successful in the discovery of new inhibitors of tubulin assembly. Accordingly, tetra-substituted alkene analogues (21-30) were designed based in part on combinations of the structural and electronic components of tamoxifen and combretastatin A-4 (CA4). The McMurry coupling reaction was used as the key synthetic step in the preparation of these tri- and tetra-arylethylene analogues. The structural assignment of E, Z isomers was determined on the basis of 2D-NOESY experiments. The ability of these compounds to inhibit tubulin polymerization and cell growth in selected human cancer cell lines was evaluated. Although the compounds were found to be less potent than CA4, these analogues significantly advance the known structure-activity relationship associated with the colchicine binding site on β-tubulin.
INDOLE-CONTAINING COMPOUNDS WITH ANTI-TUBULIN AND VASCULAR TARGETING ACTIVITY
-
Page 29, (2010/02/09)
Trimethoxyphenyl substituted indole ligands have been discovered which demonstrate impressive cytotoxicity as well as a remarkable ability to inhibit tubulin assembly. Such compounds as well as related derivatives are excellent clinical candidates for the
Tubulin binding ligands and corresponding prodrug constructs
-
, (2008/06/13)
A diverse set of tubulin binding ligands have been discovered which are structurally characterized, in a general sense, by a semi-rigid molecular framework capable of maintaining aryl-aryl, pseudo pi stacking distances appropriate for molecular recognition of tubulin. In phenolic or amino form, these ligands may be further functionalized to prepare phosphate esters, phosphate salts, and phosphoramidates capable of demonstrating selective targeting and destruction of tumor cell vasculature.
