title: Construction of Benzo[c]carbazoles and Their Antitumor Derivatives through the Diels-Alder Reaction of 2-Alkenylindoles and Arynes.
abstract: The direct assembly of benzo[c]carbazole derivatives via the Diels-Alder reaction of arynes and easily accessible 2-alkenylidoles was reported. By employing different aryne precursor loads, 6,7-dihydrobenzo[c]carbazoles or aryl-substituted 7,11b-dihydrobenzo[c]carbazoles could be controllably generated in good to excellent yields under a nitrogen atmosphere. On the other hand, when the reaction was conducted under oxygen, oxidated/aromatized product benzo[c]carbazoles could be generated directly with high selectivity and efficiency in a one-step manner. Interestingly, the benzo[c]carbazole-5-carboxamide amidation derivatives of the above products showed good antitumor activities. The inhibitory effect of these molecules against cancer cells was also described.
authors.affiliation: Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, People's Republic of China.
authors.forename: Feng
authors.initials: F
authors.lastname: Sha
authors.affiliation: Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, People's Republic of China.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Tao
authors.affiliation: Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, People's Republic of China.
authors.forename: Chen-Yu
authors.initials: CY
authors.lastname: Tang
authors.affiliation: Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, People's Republic of China.
authors.forename: Fei
authors.initials: F
authors.lastname: Zhang
authors.affiliation: Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, People's Republic of China.
authors.forename: Xin-Yan
authors.initials: XY
authors.lastname: Wu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002227:Carbazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000480:Alkynes; D000970:Antineoplastic Agents; D002227:Carbazoles; D007211:Indoles