TY - JOUR
TI - A new ring-forming methodology for the synthesis of bioactive pyrroloquinoline derivatives
AU - Vlachou, M.
AU - Tsotinis, A.
AU - Kelland, L.R.
AU - Thurston, D.E.
JO - Heterocycles
PY - 2002
VL - 57
TODO - 1
SP - 129-133
PB - Japan Institute of Heterocyclic Chemistry
SN - 0385-5414, 1881-0942
TODO - 10.3987/com-01-9373
TODO - 1h pyrrolo[2,3 f]quinoline;  1h pyrrolo[3,2 h]quinoline;  3h pyrrolo[3,2 f]quinoline;  4 chlorophenoxyacetonitrile;  5 nitroquinoline;  cisplatin;  cytotoxic agent;  potassium derivative;  potassium tert butoxide;  pyrroloquinoline derivative;  quinoline derivative;  sulforhodamine B;  tetrahydrofuran;  unclassified drug, article;  carbon nuclear magnetic resonance;  controlled study;  drug cytotoxicity;  drug synthesis;  human;  human cell;  hydrogenation;  ovary carcinoma;  proton nuclear magnetic resonance;  reaction analysis;  reaction time
TODO - A new, efficient, two-step method for the synthesis of bioactive pyrroloquinolines is described. Readily available nitroquinolines, bearing the nitro moiety in the carbocyclic ring, are treated with 4-chlorophenoxyacetonitrile in the presence of potassium tert-butoxide/THF to give the analogous vicarious nucleophilic substitution products (5, 8 and 11). These, in turn, are subjected to catalytic hydrogenation to produce 1H-pyrrolo[2,3-f]quinoline (6), 3H-pyrrolo[3,2-f]quinoline (9) and 1H-pyrrolo[3,2-h]quinoline (12) in good yields and relatively short reaction times. The differential activity of two N-alkylated 1H-pyrrolo[2,3-f]quinolines (1) in cisplatin resistant cell lines compared to the corresponding parent lines suggests that these might be useful leads for developing agents for use in drug resistant diseases.
ER -