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 RelationshipABSTRACT
TFA alone was found to be remarkably effective for the intramolecular hydroarylation (IMHA) of alkynes when employed as a solvent in the cyclization of 3-alkynyl substituted 2-(indol-3-yl)quinoxalines. This simple and metal free cyclization method afforded a range of indolophenazines as new and potential cytotoxic agents. The use of excess TFA was found to be crucial for the success of this reaction.
Subject(s)
Indoles/chemical synthesis , Phenazines/chemical synthesis , Quinoxalines/chemical synthesis , Alkynes/chemical synthesis , Alkynes/chemistry , Catalysis , Crystallography, X-Ray , Cyclization , Indoles/chemistry , Models, Molecular , Phenazines/chemistry , Quinoxalines/chemistryABSTRACT
Speech is essential to human activity, therefore phonetics must be considered with mechanics and esthetics as the cardinal factors contributing to the success of the dental prosthesis. The aim of this following procedure is to produce dentures that are mechanically functional, esthetically pleasing and permit normal speech.
