160768-75-2Relevant academic research and scientific papers
Synthesis and bioactivity of 2,4-diacyl analogues of paclitaxel
Chordia, Mahendra D.,Yuan, Haiqing,Jagtap, Prakash G.,Kadow, John F.,Long, Byron H.,Fairchild, Craig R.,Johnston, Kathy A.,Kingston, David G.I.
, p. 171 - 178 (2007/10/03)
The 2,4-diacyl paclitaxel analogues 8a-8r were prepared from paclitaxel by acylation of 4-deacetyl-2-debenzoylpaclitaxel 1,2-carbonate (3) followed either by hydrolysis of the carbonate and acylation or by direct treatment of the carbonate with an aryllithium. Some of the resulting derivatives showed significantly improved tubulin assembly activity and cytotoxicity as compared with paclitaxel; in some cases this improvement was especially significant for paclitaxel-resistant cell lines.
Synthesis and biological evaluation of novel paclitaxel (Taxol) D-ring modified analogues
Gunatilaka, A. A. Leslie,Ramdayal, Frank D.,Sarragiotto, Maria H.,Kingston, David G. I.,Sackett, Dan L.,Hamel, Ernest
, p. 2694 - 2703 (2007/10/03)
The semisynthesis and biological activity of paclitaxel (Taxol) analogues in which the oxygen atom in ring D is substituted by a sulfur or a selenium atom is presented. These derivatives were synthesized and tested in order to make more transparent the role of the oxetane ring in the biological activity of paclitaxel. The sulfur derivatives were found to be less active than paclitaxel in biological assays, while the selenium derivative could not be converted to its 4-acyl analogue. The results with the sulfur analogues suggest that the oxygen atom in the oxetane ring plays an important role in the mechanism by which paclitaxel exhibits its anticancer activity.
Preparation of phenolic paclitaxel metabolites
Park, Haeil,Hepperle, Michael,Boge, Thomas C.,Himes, Richard H.,Georg, Gunda I.
, p. 2705 - 2709 (2007/10/03)
The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3'-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)-baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.
Synthesis and Biological Evaluation of 4-Deacetylpaclitaxel
Neidigh, Kurt A.,Gharpure, Milind M.,Rimoldi, John M.,Kingston, David G. I.,Jiang, Yuan Qing,Hamel, Ernest
, p. 6839 - 6842 (2007/10/02)
4-Deacetylpaclitaxel, prepared from baccatin III via two synthetic approaches and from paclitaxel via one synthetic approach, has minimal effects on tubulin polymerization and is not cytotoxic to human CA46 Burkitt lymphoma cells.
Selective C-2 and C-4 deacylation and acylation of taxol: The first synthesis of a C-4 substituted taxol analogue
Georg,Georg, Gunda I.,Ali,Ali, Syed M.,Boge,Boge, Thomas C.,Datta,Datta, Apurba,Falborg,Falborg, Lise,Himes,Himes, Richard H.
, p. 8931 - 8934 (2007/10/02)
Hydrolytic procedures for selective 2-debenzoylation and 2,4-dideacylation of 2'-O-tert-butyldimethylsilyl-7-O-(triethylsilyl)taxol are reported. The first synthesis and biological evaluation of a 4-substituted analogue, 4-deacetyl-4-isobutanoyltaxol, is
Synthesis and Biological Evaluation of 4-Deacetoxypaclitaxel
Chordia, Mahendra D.,Chaudhary, Ashok G.,Kingston, David G. I.,Jiang, Yuan Qing,Hamel, Ernest
, p. 6843 - 6846 (2007/10/02)
4-Deacetoxypaclitaxel (9) has been prepared in seven steps from paclitaxel (Taxol).It is significantly less active than paclitaxel in tubulin-assembly and cytotoxicity bioassays.
