162465-29-4Relevant articles and documents
Synthesis of cryptothilone 1, the first cryptophycin-epothilone hybrid
White, James D.,Smits, Helmars,Hamel, Ernest
, p. 3947 - 3950 (2007/10/03)
A hybrid structure was synthesized in which one portion is characteristic of a cryptophycin and a second sector bears the signature of an epothilone. The hybrid, in contrast to parent cryptophycin and epothilone systems, showed no effect on the tubulin as
A synthesis of cryptophycin 4 using a planar chiral molybdenum cationic complex
Christopher, John A.,Kocienski, Philip J.,Kuhl, Alexander,Bell, Richard
, p. 463 - 466 (2007/10/03)
A synthesis of cytotoxic agent Cryptophycin 4 features a new approach to (5S,6R)-5-hydroxy-6-methyl-8-phenyl-(2E,7E)-dienoic acid in which the anti stereochemistry between two stereogenic centres is secured by addition of a 1,3-dioxan-4-ylcopper(I) reagen
Novel cryptophycin antitumor agents: Synthesis and cytotoxicity of fragment 'B' analogues
Patel, Vinod F.,Andis, Sherri L.,Kennedy, Joseph H.,Ray, James E.,Schultz, Richard M.
, p. 2588 - 2603 (2007/10/03)
A general synthetic approach to novel cryptophycin analogues 6 is described. N-Hydroxysuccinimide active ester 15, a key common intermediate, was converted to β-epoxide 6 in three steps, via initial coupling with unprotected amino acid 9, followed by deprotection/macrolactamization of acyclic precursor 16, and final oxidation of styrene 7 to install the C7-C8 β-epoxide. Cryptophycin styrenes 7 and β-epoxides 6, bearing diverse side chains in fragment 'B', were evaluated for cytotoxic activity, β-Epoxides 6, in general, were significantly more potent than the corresponding α-epoxides 17 and styrenes 7. A benzyl side chain was required for potent activity, with β-epoxide 6u, possessing a 3-Cl,4-(dimethylamino)benzyl moiety, as the most potent cytotoxic agent prepared, with an IC50 = 54 pM, only 2-fold-less than that of Cryptophycin-52 (3).