TY - JOUR
T1 - Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones
AU - Hehir, Sarah
AU - O'Donovan, Liz
AU - Carty, Michael P.
AU - Aldabbagh, Fawaz
PY - 2008/5/5
Y1 - 2008/5/5
N2 - Upon thermolysis 5,6-dimethyl-N-[(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-(trans)-2,3-diphenylaziridin-1-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2-a]benzimidazoles in 70, 50, 77 and 11% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells.
AB - Upon thermolysis 5,6-dimethyl-N-[(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-(trans)-2,3-diphenylaziridin-1-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2-a]benzimidazoles in 70, 50, 77 and 11% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells.
KW - Antitumor agents
KW - Aziridinylimines
KW - Cycloaddition
KW - Heterocycles
UR - http://www.scopus.com/inward/record.url?scp=41549123952&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2008.02.093
DO - 10.1016/j.tet.2008.02.093
M3 - Article
AN - SCOPUS:41549123952
SN - 0040-4020
VL - 64
SP - 4196
EP - 4203
JO - Tetrahedron
JF - Tetrahedron
IS - 19
ER -