203448-41-3Relevant academic research and scientific papers
Antineoplastic agents. 379. Synthesis of phenstatin phosphate
Pettit, George R.,Toki, Brian,Herald, Delbert L.,Verdier-Pinard, Pascal,Boyd, Michael R.,Hamel, Ernest,Pettit, Robin K.
, p. 1688 - 1695 (1998)
A structure-activity relationship (SAR) study of the South African willow tree (Combretum caffrum) antineoplastic constituent combretastatin A- 4 (1b) directed at maintaining the (Z)stilbene relationship of the olefin diphenyl substituents led to synthesis of a potent cancer cell growth inhibitor designated phenstatin (3b). Initially phenstatin silyl ether (3a) was unexpectedly obtained by Jacobsen oxidation of combretastatin A-4 silyl ether (1c → 3a), and the parent phenstatin (3b) was later synthesized (6a → 3a → 3b) in quantity. Phenstatin was converted to the sodium phosphate prodrug (3d) by a dibenzyl phosphite phosphorylation and subsequent hydrogenolysis sequence (3b → 3c → 3d). Phenstatin (3b) inhibited growth of the pathogenic bacterium Neisseria gonorrhoeae and was a potent inhibitor of tubulin polymerization and the binding of colchicine to tubulin comparable to combretastatin A-4 (1b). Interestingly, the prodrugs were found to have reduced activity in these biochemical assays. While no significant tubulin activity was observed with the phosphorylated derivative of combretastatin A- 4 (1d), phosphate 3d retained detectable inhibitory effects in both assays.
Synthesis of phenstatin and prodrugs thereof
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Page/Page column 2; 8; 9, (2008/06/13)
A newly discovered antineoplastic compound denominated “phenstatin” is herein described as are synthetic methods for producing phenstatin and the active prodrug thereof. Phenstatin was converted to the sodium phosphate prodrug (3d) by a dibenzylphosphite
A ROMPGEL-supported N-hydroxysuccinimide: A host of acylations with minimal purification
Barrett, Anthony G. M.,Cramp, Susan M.,Roberts, Richard S.,Zecri, Frederic J.
, p. 261 - 264 (2007/10/03)
(formula presented) amides, carbamates, ureas, Weinreb amides, hydroxamic acids Yields 89-98% Purity > 95% A novel N-hydroxysuccinimide ring-opening metathesis polymer is described as a recyclable supported acyl transfer reagent. Amides, carbamates, ureas, Weinreb amides, and hydroxamic acids are all obtained in excellent yields and purities from amines with minimal purification.
Impurity annihilation; a strategy for solution phase combinatorial chemistry with minimal purification
Barrett, Anthony G. M.,Smith, Marie L.,Zecri, Frederic J.
, p. 2317 - 2318 (2007/10/03)
The selective annihilation of all contaminants in the solution phase formation of amides or sulfonamides is accomplished by their incorporation into a polyurea and removal by filtration.
