144465-79-2Relevant academic research and scientific papers
Rotational-echo double-resonance NMR distance measurements for the tubulin-bound paclitaxel conformation
Paik, Younkee,Yang, Chao,Metaferia, Belhu,Tang, Shoubin,Bane, Susan,Ravindra, Rudravajhala,Shanker, Natasha,Alcaraz, Ana A.,Johnson, Scott A.,Schaefer, Jacob,O'Connor, Robert D.,Cegelski, Lynette,Snyder, James P.,Kingston, David G. I.
, p. 361 - 370 (2008/02/09)
The important anticancer drug Taxol (paclitaxel, PTX) owes its unique activity to its ability to bind to tubulin in a stoichiometric ratio and promote its assembly into microtubules. The conformation of the microtubule-bound drug has been the focus of num
Synthesis of new fluorine-containing taxoids by means of β-lactam synthon method
Ojima,Kuduk,Slater,Gimi,Sun
, p. 209 - 224 (2007/10/02)
A series of new fluorine-containing analogs of paclitaxel and docetaxel are synthesized using the coupling of (3R,4S)-1-acyl-β-lactams with high enantiomeric purity with properly protected baccatin III, 10-deacetylbaccatin III, and 14β-hydroxy-10-deacetyl
New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method
Ojima, Iwao,Habus, Ivan,Zhao, Mangzhu,Zucco, Martine,Park, Young Hoon,Sun, Chung Ming,Brigaud, Thierry
, p. 6985 - 7012 (2007/10/02)
Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.
New and efficient routes to norstatine and its analogs with high enantiomeric purity by β-Lactam Synthon Method
Ojima, Iwao,Park, Young Hoon,Sun, Chung Ming,Brigaud, Thierry,Zhao, Mangzhu
, p. 5737 - 5740 (2007/10/02)
Norstatine and its analogs, i.e., 3-amino-2-hydroxyalkanoic acids, with high enantiomeric purity are obtained through effecient asymmetric synthesis of 3-silyloxy-β-lactams by chiral enolate - imine cyclocondensation, followed by hydrolysis.
