460740-51-6Relevant academic research and scientific papers
Studies on Bergman cyclization, the chemistry at the heart of enediynes
Basak, Amit,Bdour, Hussam Moh'd,Shain, Jagadish C.
, p. 679 - 688 (2007/10/03)
The kinetics of Bergman cyclization (BC) which is dependent upon a number of steric and stereoelectronic parameters, have been studied in various nitrogen-substituted cyclic enediynes. The simplest of these, a 10-membered enediyne 33 cyclized spontaneously (t1/2 = 72 h at 23°) and caused significant cleavage of supercoiled double stranded DNA at micromolar level. The degree of pyramidalization of the ring nitrogen in these enediynes has an inverse effect on the rate of cyclization. Replacement of the ene part with an aromatic ring led to a considerable elevation of activation energy for BC.
