Synthesis and antibacterial activity of littorachalcone and related diphenyl ethers

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 7, 2008, Pages 2329-2332

  Kraus, George A ^a   Kumar, Ganesh ^a   Phillips, Gregory ^a   Michalson, Kris ^a   Mangano, Maria ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Aldol; Antibacterials; Chalcones

Indexed keywords

ALDEHYDE DERIVATIVE; CHALCONE DERIVATIVE; LITTORACHALCONE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG DETERMINATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; STRUCTURE ANALYSIS; WITTIG REACTION;

ANTI-BACTERIAL AGENTS; BACTERIA; CHALCONE; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; PHENYL ETHERS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 41249096308     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.02.082     Document Type: Article

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15. Experimental and spectral data for title compounds: 5-Methyl-2-(4-methylphenoxy)-phenol (6). To the stirred solution of p-tolyl ether (1.98 g, 10 mmol) in 20 mL of THF and 20 mL of ether, n-BuLi (2.5 M solution in hexane, 4.4 mL, 11 mmol) was added at rt. This solution was boiled for 6 h. Trimethyl borate (1.14 g, 11.0 mmol) was then added dropwise. The resulting mixture was boiled for an additional 6 h. The reaction was cooled to 0 °C and hydrogen peroxide (30% solution in water, 12 mL) followed by aqueous sodium hydroxide (3 N, 12 mL) solution was added. It was stirred at rt for 1 h and then at 40 °C for 2 h, acidified with 10% HCl and then extracted with ethyl acetate.