Epothilone D (synthetic)
|CAS No.: 189453-10-9||Request for quotation|
Epothilone D (Epo-D) is a paclitaxel-like microtubule-stabilizing agent that was isolated from the myxobacterium Sorangium cellulosum. Although epothilone D can inhibit proliferation in multiple tumor cell lines, the effect of epothilone D on neointimal hyperplasia after angioplasty has not been reported. Some experiment result that epothilone D may regulate the cell cycle G1-checkpoint proteins as its major molecular mechanism for inhibiting neointimal hyperplasia after in vivo rat carotid artery injury.
The 9-(S)-Epo D and 9-(R)-Epo D demonstrated significant difference in inhibition activities against cancer cell lines and in conformational analysis.
The ring-opening or ring fragmentation reactions of cyclopropanol intermediates are used in the total synthesis of epothilone D for the creation of trisubstituted double bonds, an ethyl ketone functionality, as well as for the protection of carboxylic and ester groups. Epothilone D is obtained in 1.6% overall yield (24 steps in the longest linear sequence) starting from (R)-methyl 2,3-O-isopropylideneglycerate. The key cyclopropanol intermediates are efficiently obtained by titanium(IV)-catalyzed reactions of readily available esters with Grignard reagents.
Epothilone D Specification
|Appearance||White Crystalline powder||Standard Packing||50mg/bag or per customer request|
|Purity (HPLC)||≥ 98%||Inventory||Normally we have Epothilone D in stock|
|Melting Point:||63 - 66 °|
|Epothilone D physical parameters|
|Synonym||(4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione; (-)-Desoxyepothilone B; (-)-Epothilone D; 12,13-Deoxyepothilone B; 12,13-Desoxyepothilone B; Desoxyepothilone B; Epo D; Epothilone D; KOS 862; NSC 703147;|
|Certificate of Analysis||Epothilone D COA|
|Literature||Epothilone D literature|
|MSDS||Epothilone D MSDS|
|1.||Tack-Joong Kim et al: Vascular Pharmacology, 47(4) 2007, 229-237 "Epothilone D, a microtubule-stabilizing compound, inhibits neointimal hyperplasia after rat carotid artery injury by cell cycle arrest via regulation of G1-checkpoint proteins"|
|2.||Feng Sang et al: European Journal of Medicinal Chemistry, 68 (2013) 321-332 "Epothilone D and its 9-Methyl analogues: Combinatorial syntheses, conformation, and biological activities"|
|3||Robert L. Broadrup et al: Bioorganic Chemistry, 33(2) 2005 116–133. "Total synthesis of 12,13-desoxyepothilone B (Epothilone D)"|
|4.||Alaksiej L.Hurski et al: Tetrahedron Letters 51(27) 2010,3497–3500 "Total synthesis of epothilone D by sixfold ring cleavage of cyclopropanol intermediates."|
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