title: Synthesis and anti-cancer activity of 1,4-disubstituted imidazo[4,5-c]quinolines.
abstract: The synthesis and anti-cancer activity evaluation of fused imidazoquinoline compounds is reported in this paper. Yb(OTf)3 has been utilized as a catalyst for the synthesis of 1,4-diaryl substituted imidazo[4,5-c]quinolines via a modified Pictet-Spengler approach. The desired imidazole ring was synthesized from imines using TosMIC (toluenesulfonylmethyl isocyanide) and subsequently functionalized at the C-4 position yielding an imidazoquinoline skeleton. Importantly, the final step was carried out without the aid of any prefunctionalization to obtain the resultant compounds in good yields. The synthesized compounds, when screened for anti-cancer activity, revealed the highest activity with 4-(2-bromophenyl)-1-phenyl-1H-imidazo[4,5-c]quinoline (IC50: 103.3 μM).
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science-Pilani (Hyderabad Campus), Hyderabad-500078, India. anupam@hyderabad.bits-pilani.ac.in.
authors.forename: Yadagiri
authors.initials: Y
authors.lastname: Thigulla
authors.forename: Mahesh
authors.initials: M
authors.lastname: Akula
authors.forename: Prakruti
authors.initials: P
authors.lastname: Trivedi
authors.forename: Balaram
authors.initials: B
authors.lastname: Ghosh
authors.forename: Mukund
authors.initials: M
authors.lastname: Jha
authors.forename: Anupam
authors.initials: A
authors.lastname: Bhattacharya
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: C000611049:4-(2-bromophenyl)-1-phenyl-1H-imidazo(4,5-c)quinoline; D000970:Antineoplastic Agents; D007093:Imidazoles; D011804:Quinolines