title: Efficient synthesis of isobenzofuran-1(3H)-ones (phthalides) and selected biological evaluations.
abstract: The studies presented here deal with the convenient and efficient one-step conversion of o-alkylbenzoic acids into their corresponding isobenzofuran-1 (3H)-ones (phthalides) using NaBrO3/NaHSO3 in a two-phase system. A range of o-alkylbenzoic acids was used with the object of getting a variety of phthalide derivatives as multipurpose biologically active compounds. Seventeen phthalides have been synthesized and tested for cytotoxicity, antibacterial and antifungal activities. Some of these compounds showed promising cytotoxic effects against Artemia salina. Compounds 4j-4p were highly active against Gram-negative and Gram-positive bacteria among all tested compounds. In the fungicidal assay, the compounds showed a broad spectrum of activity against six fungi. All compounds were characterized via elemental analysis, UV, IR, mass and-NMR spectroscopy.
authors.affiliation: Institut für Organische Chemie der Universität Tübingen, Tübingen, Germany.
authors.forename: Ernst
authors.initials: E
authors.lastname: Bayer
authors.forename: Safdar
authors.initials: S
authors.lastname: Hayat
authors.lastname: Atta-ur-Rahman
authors.forename: M Iqbal
authors.initials: MI
authors.lastname: Choudhary
authors.forename: Khalid Mohammed
authors.initials: KM
authors.lastname: Khan
authors.forename: Syed Tasadaque Ali
authors.initials: ST
authors.lastname: Shah
authors.forename: M
authors.initials: M
authors.lastname: Imran-ul-Haq
authors.forename: M Usman
authors.initials: MU
authors.lastname: Anwar
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Voelter
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology; D000935:Antifungal Agents / Q000494:pharmacology; D001156:Artemia; D001419:Bacteria / Q000187:drug effects; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D007202:Indicators and Reagents; D007928:Lethal Dose 50; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001572:Benzofurans; D007202:Indicators and Reagents; C082022:phthalide