title: Synthesis and antibacterial evaluation of typharin analog: 6,8-dihydroxy-7-methyl-3-styryl-3,4-dihydroisocoumarin.
abstract: Synthesis of the 6-hydroxy-7-methyl analog of typharin (8-dihydroxy-3-styryl-3,4-dihydroisocoumarin) isolated from the rhizomes of Typha capensis has been described. Direct condensation of 3,5-dimethoxy-4-methylhomophthalic acid (1) with cinnamoyl chloride at elevated temperature under inert conditions afforded 6,8-dihydroxy-7-methyl-3-styrylisocoumarin (2). Hydrolysis of isocoumarin to keto acid (3) followed by reduction and cyclodehydration of hydroxy acid analog (4) afforded ( ± )-6,8-dimethoxy-3-(4-methoxyphenyl)-3,4-dihydroisocoumarin (5). Demethylation of the latter using anhydrous aluminum chloride/ethane thiol furnished the title isocoumarin (6). Compounds (1-6) were screened for in vitro antibacterial activity against a representative panel of Gram-positive and Gram-negative bacteria using levofloxacin as the reference drug.
authors: Department of Chemistry, Quaid-I-Azam University 45320, Islamabad, Pakistan. aamersaeed@yahoo.com
authors: Aamer
authors: A
authors: Saeed
authors: Hummera
authors: H
authors: Rafique
authors: Zaman
authors: Z
authors: Ashraf
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D049934:Isocoumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D064704:Levofloxacin; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D015242:Ofloxacin / Q000494:pharmacology; D027343:Rhizome / Q000737:chemistry; D032401:Typhaceae / Q000737:chemistry
chemical_list: C579834:6,8-dihydroxy-7-methyl-3-styryl-3,4-dihydroisocoumarin; D000900:Anti-Bacterial Agents; D049934:Isocoumarins; C473707:typharin; D064704:Levofloxacin; D015242:Ofloxacin