Efficient synthesis of isobenzofuran-1(3H)-ones (phthalides) and selected biological evaluations.
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.
Bayer
Ernst
E
Institut für Organische Chemie der Universität Tübingen, Tübingen, Germany.
Hayat
Safdar
S
Atta-ur-Rahman
Choudhary
M Iqbal
MI
Khan
Khalid Mohammed
KM
Shah
Syed Tasadaque Ali
ST
Imran-ul-Haq
M
M
Anwar
M Usman
MU
Voelter
Wolfgang
W
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
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001572:Benzofurans; D007202:Indicators and Reagents; C082022:phthalide