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Org Biomol Chem ; 15(20): 4468-4476, 2017 May 23.
Article in English | MEDLINE | ID: mdl-28497830

ABSTRACT

Various oxepine and azepine fused N-heterocyclic derivatives were synthesized using a new and one-pot reaction of 2,3-dichloro quinoxaline/pyrazine with 2-(1H-indol-2-yl)phenol/aniline in the presence of 25 mol% FeCl3. The reaction proceeded via C-C bond followed by C-X (X = O or N) bond formation to construct the central 7-membered ring, affording the desired products in good yields. The structure assignment was confirmed by the single crystal X-ray analysis of a synthesized oxepine fused N-heterocycle derivative. Most of the synthesized compounds were found to be promising when tested for their anti-proliferative properties against cervical and breast cancer cell lines.


Subject(s)
Antineoplastic Agents/pharmacology , Azepines/pharmacology , Chlorides/chemistry , Ferric Compounds/chemistry , Heterocyclic Compounds/pharmacology , Indoles/pharmacology , Oxepins/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Azepines/chemical synthesis , Azepines/chemistry , Catalysis , Cell Line, Tumor , Cell Proliferation/drug effects , Crystallography, X-Ray , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , HeLa Cells , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/chemistry , Humans , Indoles/chemistry , MCF-7 Cells , Models, Molecular , Molecular Structure , Oxepins/chemical synthesis , Oxepins/chemistry , Structure-Activity Relationship
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