On the total synthesis and preliminary biological evaluations of 15(R) and 15(S) aza-dEpoB: A Mitsunobu inversion at C15 in pre-epothilone fragments Journal Article
| Authors: | Stachel, S. J.; Chappell, M. D.; Lee, C. B.; Danishefsky, S. J.; Chou, T. C.; He, L.; Horwitz, S. B. |
| Article Title: | On the total synthesis and preliminary biological evaluations of 15(R) and 15(S) aza-dEpoB: A Mitsunobu inversion at C15 in pre-epothilone fragments |
| Abstract: | (Equation Presented) The syntheses of two epothilone analogues, 15(S)-aza-12,13-desoxyepothilone B and the epimeric 15(R)-aza-12,13-desoxyepothilone B, are described. A Mitsunobu inversion was utilized for elaboration of pre-epothilone fragments to the corresponding macrolactam. Tubulin binding and cytotoxicity profiles of these analogues are presented. |
| Keywords: | antineoplastic agents; comparative study; antineoplastic agent; metabolism; cell survival; drug effect; tumor cells, cultured; chemistry; cell culture; thiazoles; tubulin; heterocyclic compound; synthesis; epothilones; epothilone b; epothilone derivative; epoxy compounds; lactones; thiazole derivative; lactone; epoxide; aza compounds; humans; human; article; desoxyepothilone b; 15 aza 12,13 desoxyepothilone b; 15-aza-12,13-desoxyepothilone b |
| Journal Title: | Organic Letters |
| Volume: | 2 |
| Issue: | 11 |
| ISSN: | 1523-7060 |
| Publisher: | American Chemical Society |
| Date Published: | 2000-06-01 |
| Start Page: | 1637 |
| End Page: | 1639 |
| Language: | English |
| PUBMED: | 10841498 |
| PROVIDER: | scopus |
| DOI: | 10.1021/ol005932m |
| DOI/URL: | |
| Notes: | Export Date: 18 November 2015 -- Source: Scopus |
Altmetric
Citation Impact
BMJ Impact Analytics
MSK Authors
-
7Lee -
8
Chappell -
13
Stachel -
539Danishefsky -
319Chou
Related MSK Work