Synthesis and biological evaluation of novel C (7) modified chrysin analogues as antibacterial agents

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 1, 2006, Pages 221-224

  Suresh Babu, K ^a   Hari Babu, T ^a   Srinivas, P V ^a   Hara Kishore, K ^a   Murthy, U S N ^a   Rao, J Madhusudana ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Amines; Antibacterial activity; Chrysin; Oroxylum indicum; Spacers

Indexed keywords

ANTIINFECTIVE AGENT; CHRYSIN;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SPHAERICUS; BACILLUS SUBTILIS; CHROMOBACTERIUM; CONTROLLED STUDY; DRUG SCREENING; DRUG SENSITIVITY; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; KLEBSIELLA AEROGENES; MEDICINAL PLANT; NONHUMAN; OROXYLUM INDICUM; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

ANTI-ALLERGIC AGENTS; ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; CARBON; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; FLAVONOIDS; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; MORPHOLINES; PLANT EXTRACTS; STRUCTURE-ACTIVITY RELATIONSHIP;

BACILLUS SPHAERICUS; BACILLUS SUBTILIS; CHROMOBACTERIUM; KLEBSIELLA AEROGENES; NEGIBACTERIA; OROXYLUM INDICUM; POSIBACTERIA; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 27744513113     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.09.009     Document Type: Article

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23. General procedure for the preparation of 7-O-alkylamino derivatives of chrysin: (i) General procedure for the preparation of 7-O-alkyl derivatives of chrysin (2a-2c): To a mixture of chrysin 1 (1 g, 3.93 mmol) and anhydrous potassium carbonate (0.81 g, 5.8 mmol) in 20 ml acetone, corresponding dibromoalkane (1,3-dibromo propane for 2a, 1,4-dibromo butane for 2b, and 1,6-dibromo hexane for 2c were added. The mixture was refluxed under nitrogen atmosphere for 3-4 h. After completion of the reaction, potassium carbonate was filtered and washed with excess acetone (2× 50 ml). The combined acetone layers were concentrated under vacuum. The residue was purified by column chromatography on silica gel (60-120 mesh) to yield 7-O-bromoalkyl chrysin (2a, 2b, and 2c) in pure form. (ii) General procedure for the preparation of 7-O-alkyl derivatives of chrysin: To a mixture of bromoalkyl chrysin (2a, 2b, and 2c) and anhydrous potassium carbonate (2.41 g, 17.2 mmol) in 20 ml acetonitrile, the corresponding amine was added. The mixture was refluxed under nitrogen atmosphere for 3-4 h. After completion of the reaction, the reaction mixture was brought to room temperature and was poured into ice water and washed with methylene chloride (2× 10 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography on silica gel (60-120 mesh) to give the corresponding 7-O-alkylamino derivatives of chrysin (3a-3d, 4a-4d, and 5a-5d) in very good yields (60-80%).
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