Τίτλος:
A new ring-forming methodology for the synthesis of bioactive pyrroloquinoline derivatives
Γλώσσες Τεκμηρίου:
Αγγλικά
Περίληψη:
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.
Συγγραφείς:
Vlachou, M.
Tsotinis, A.
Kelland, L.R.
Thurston, D.E.
Εκδότης:
Japan Institute of Heterocyclic Chemistry
Λέξεις-κλειδιά:
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
