12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents was written by Nicolaou, K. C.;Rhoades, Derek;Wang, Yanping;Bai, Ruoli;Hamel, Ernest;Aujay, Monette;Sandoval, Joseph;Gavrilyuk, Julia. And the article was included in Journal of the American Chemical Society in 2017.Name: 4-(Bromomethyl)-2-methylthiazole The following contents are mentioned in the article:
The synthesis and biol. evaluation of a series of 12,13-aziridinyl epothilone B analogs is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic Me ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif was achieved by application of the Ess-Kurti-Falck aziridination, while the heterocyclic side chains were introduced via stereoselective phosphonate-based olefinations. In order to ensure high (E) selectivities for the latter reaction for electron-rich heterocycles, it became necessary to develop and apply an unprecedented modification of the venerable Horner-Wadsworth-Emmons reaction, employing 2-fluoroethoxyphosphonates that may prove to be of general value in organic synthesis. These studies resulted in the discovery of some of the most potent epothilones reported to date. Equipped with functional groups to accommodate modern drug delivery technologies, some of these compounds exhibited picomolar potencies that qualify them as payloads for antibody drug conjugates (ADCs), while a number of them revealed impressive activities against drug resistant human cancer cells, making them desirable for potential medical applications. This study involved multiple reactions and reactants, such as 4-(Bromomethyl)-2-methylthiazole (cas: 74704-39-5Name: 4-(Bromomethyl)-2-methylthiazole).
4-(Bromomethyl)-2-methylthiazole (cas: 74704-39-5) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Name: 4-(Bromomethyl)-2-methylthiazole
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica