TY - JOUR
T1 - The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4
AU - Flynn, Bernard L.
AU - Flynn, Guy P.
AU - Hamel, Ernest
AU - Jung, M. Katherine
PY - 2001/9/3
Y1 - 2001/9/3
N2 - A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3-5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than 1 but exhibit comparable activity to the most active of the benzo[b]thiophenes 3-5. A structure-activity relationship of these compounds is considered.
AB - A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3-5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than 1 but exhibit comparable activity to the most active of the benzo[b]thiophenes 3-5. A structure-activity relationship of these compounds is considered.
UR - http://www.scopus.com/inward/record.url?scp=0035801759&partnerID=8YFLogxK
U2 - 10.1016/S0960-894X(01)00436-X
DO - 10.1016/S0960-894X(01)00436-X
M3 - Article
SN - 0960-894X
VL - 11
SP - 2341
EP - 2343
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 17
ER -