title: Synthesis and pharmacological activity of O-aminoalkyl derivatives of 7-hydroxycoumarin.
abstract: A series of novel O-aminoalkyl substituted 7-hydroxycoumarins were synthesized and evaluated for antibacterial and anticancer toxicity. Two different synthetic procedures, conventional and microwave assisted were used, and the structures of the compounds were confirmed by IR, 1H, 13C NMR and MAS spectroscopic data. The molecular and crystal structures of 8-acetyl-7-[2-(1-morpholino)ethoxy]4-methylchromen-2-one in solid state were analyzed by single crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P2(1)/c. The main driving forces for the supramolecular structure are the C-H⋯O hydrogen bonds and the π⋯π intermolecular interactions. The most active compounds are those, where the O-aminoalkyl substituent has N,N-diethylamino part, and acetyl group is at C6 or at C8 atoms.
authors: Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Strasse, 02 097 Warsaw, Poland.
authors: Joanna
authors: J
authors: Trykowska Konc
authors: Elżbieta
authors: E
authors: Hejchman
authors: Hanna
authors: H
authors: Kruszewska
authors: Irena
authors: I
authors: Wolska
authors: Dorota
authors: D
authors: Maciejewska
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014468:Umbelliferones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D010091:Oximes; D014468:Umbelliferones; C031477:7-hydroxycoumarin