title: A general synthesis of arylindoles and (1-arylvinyl)carbazoles via a one-pot reaction from N-tosylhydrazones and 2-nitro-haloarenes and their potential application to colon cancer.
abstract: A convergent and effective synthesis of 3-aryl-indoles, 2,3-diaryl indoles, and (1-arylvinyl)carbazoles from a one-pot sequence involving the coupling of N-tosylhydrazones with ortho-nitro-haloarenes followed by a cyclization has been developed. Compound 5i exhibits excellent antiproliferative activity in the low nM range against colon cancer cell lines.
authors.affiliation: BioCIS, Equipe Labellisée Ligue Contre le Cancer, Univ. Paris-Sud, CNRS, University Paris-Saclay, 92290, Châtenay-Malabry, France. abdallah.hamze@u-psud.fr and Laboratory for Medicinal Chemistry and Natural Products, Lebanese University, Faculty of Sciences (1) and PRASE-EDST, Hadath, Beirut, Lebanon.
authors.forename: Tourin
authors.initials: T
authors.lastname: Bzeih
authors.affiliation: BioCIS, Equipe Labellisée Ligue Contre le Cancer, Univ. Paris-Sud, CNRS, University Paris-Saclay, 92290, Châtenay-Malabry, France. abdallah.hamze@u-psud.fr.
authors.forename: Timothée
authors.initials: T
authors.lastname: Naret
authors.affiliation: Laboratory for Medicinal Chemistry and Natural Products, Lebanese University, Faculty of Sciences (1) and PRASE-EDST, Hadath, Beirut, Lebanon.
authors.forename: Ali
authors.initials: A
authors.lastname: Hachem
authors.affiliation: Laboratory for Medicinal Chemistry and Natural Products, Lebanese University, Faculty of Sciences (1) and PRASE-EDST, Hadath, Beirut, Lebanon.
authors.forename: Nada
authors.initials: N
authors.lastname: Jaber
authors.affiliation: Laboratory for Medicinal Chemistry and Natural Products, Lebanese University, Faculty of Sciences (1) and PRASE-EDST, Hadath, Beirut, Lebanon.
authors.forename: Ali
authors.initials: A
authors.lastname: Khalaf
authors.affiliation: Institut de Chimie des Substances Naturelles, UPR 2301, CNRS avenue de la terrasse, F-91198 Gif sur Yvette, France.
authors.forename: Jerome
authors.initials: J
authors.lastname: Bignon
authors.affiliation: BioCIS, Equipe Labellisée Ligue Contre le Cancer, Univ. Paris-Sud, CNRS, University Paris-Saclay, 92290, Châtenay-Malabry, France. abdallah.hamze@u-psud.fr.
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.affiliation: BioCIS, Equipe Labellisée Ligue Contre le Cancer, Univ. Paris-Sud, CNRS, University Paris-Saclay, 92290, Châtenay-Malabry, France. abdallah.hamze@u-psud.fr.
authors.forename: Mouad
authors.initials: M
authors.lastname: Alami
authors.affiliation: BioCIS, Equipe Labellisée Ligue Contre le Cancer, Univ. Paris-Sud, CNRS, University Paris-Saclay, 92290, Châtenay-Malabry, France. abdallah.hamze@u-psud.fr.
authors.forename: Abdallah
authors.identifier: http://orcid.org/0000-0001-8425-1971
authors.initials: A
authors.lastname: Hamze
mesh_terms: D002227:Carbazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D003110:Colonic Neoplasms / Q000188:drug therapy / Q000473:pathology*; D003500:Cyclization; D006801:Humans; D006835:Hydrazones / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry*; D014407:Tumor Cells, Cultured
chemical_list: D002227:Carbazoles; D006835:Hydrazones; D006841:Hydrocarbons, Aromatic; D007211:Indoles; D009574:Nitro Compounds; D014105:Tosyl Compounds