194613-70-2Relevant academic research and scientific papers
Probing cytochrome P450-mediated activation with a truncated azinomycin analogue
Vinader, Victoria,Sadiq, Maria,Sutherland, Mark,Huang, Mengying,Loadman, Paul M.,Elsalem, Lina,Shnyder, Steven D.,Cui, Hongjuan,Afarinkia, Kamyar,Searcey, Mark,Patterson, Laurence H.,Pors, Klaus
, p. 187 - 191 (2015)
A deactivated alkene precursor (IC50 = 81 μM) to the azinomycin epoxide natural product can be bioactivated by several cytochromes P450 (CYP) to generate antiproliferative metabolites with increased potency (IC50 = 1-30 μM) in CHOwt cells. CYP1A1 and 3A4 were shown to generate exclusively the unnatural and the natural-configured azinomycin epoxide diastereoisomer respectively, while CYP1B1 produced both epoxides in a 3:1 mixture. The antiproliferative activity is linked to DNA damage as demonstrated using the comet assay. This journal is
Synthesis of (-)-octalactin A by a strategic vanadium-catalyzed oxidative kinetic resolution
Radosevich, Alexander T.,Chan, Vincent S.,Shih, Hui-Wen,Toste, F. Dean
, p. 3755 - 3758 (2008/12/23)
(Chemical Equation Presented) Both products of the kinetic resolution were used in the resolution/recombination approach shown in the scheme for the enantioselective total synthesis of (-)-octalactin A. Bn=benzyl, TBS=tert-butyldimethylsilyl.
Efficient stereoselective synthesis of the epoxyacid fragment of the azinomycins
Coleman, Robert S.,Sarko, Christopher R.,Gittinger, Jens P.
, p. 5917 - 5920 (2007/10/03)
Three concise enantioselective synthetic routes to the C17-C21 epoxyacid segment of the azinomycins are presented and were based on a Sharpless asymmetric epoxidation/kinetic resolution of racemic allylic alcohol (±)-3 that occurred with reversal of the expected sense of enantioselection.
