Noncovalent self-assembly of bicyclo[4.2.2]diketopiperazines: influence of saturation in the bridging carbacyclic ring.
[structure: see text] We have prepared 7,9-diazabicyclo[4.2.2]dec-3-ene-8,10-dione (3) and 7,9-diazabicyclo[4.2.2]decane-8,10-dione (4), which differ by virtue of the degree of unsaturation in the bridging carbacyclic tether on a 2,5-diketopiperazine. Remarkably different self-assembly patterns were observed in the solid state for the two compounds, attributed to subtle variations in the conformational constraints imposed by the tether.
Du
Yanming
Y
Drug Discovery Division, Johnson & Johnson Pharmaceutical Research and Development, Spring House, Pennsylvania 19477, USA.
Creighton
Christopher J
CJ
Tounge
Brett A
BA
Reitz
Allen B
AB