Synthesis and biological evaluation of indolyl chalcones as antitumor agents

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 13, 2010, Pages 3916-3919

  Kumar, Dalip ^a   Kumar, N Maruthi ^a   Akamatsu, Kanako ^b   Kusaka, Eriko ^b   Harada, Hiroshi ^b   Ito, Takeo ^b  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

1,3 Diaryl 2 propen 1 ones; Anticancer agents; Indolyl chalcones

Indexed keywords

ANTINEOPLASTIC AGENT; INDOLYL CHALCONE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHALCONES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

AGOUTI PACA;

EID: 77954316234     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.05.016     Document Type: Article

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30. Synthesis of indolyl chalcones 3a-m: A mixture of indol-3-carboxaldehyde 5 (1 mmol) and appropriate acetophenone 6 (1 mmol) in anhydrous ethanol (30 mL) was refluxed in presence of piperidine (0.5 mL) for 20 h. The reaction mixture was poured onto crushed ice, neutralized with acetic acid to afford solid compound which was filtered and recrystallized from ethanol to obtain pure 3a-m.
31. + 266.0936, obsd 266.0981.
32. Synthesis of indolyl chalcones 4a-j: To a solution of 3-acetylindole 7 (1 mmol) and appropriate aldehyde 8 (1 mmol) in ethanol (20 mL) was added 10% sodium hydroxide (2 mL) and refluxed the reaction mixture for 15 h. The contents of reaction mixture were poured into ice-cold water and neutralized with dilute hydrochloric acid. The solid so obtained was filtered, dried and recrystallized from ethanol to afford pure 4a-j.
33. + 292.1293, obsd 292.1335.
34. 4 cells well in 96-well plates, the day before chalcones (3 and 4) treatment. All the compounds were dissolved in dimethylsulfoxide (DMSO) at room temperature. Aliquots of these stock solutions at 100 mM were stored at -20 °C. The cell viability was measured by the cell Counting Kit-8 (Dojin, Kumamoto, Japan) using a spectrophotometer (xMark; Bio-Rad, Hercules, CA, USA) at 450 nm after 24 h and 48 h of chalcones treatment. Final concentrations of the vehicle were 1% DMSO in culture medium. The cell viability of A-549, PaCa-2 and PC-3 human cancer cells was inhibited by the chalcone analogues 3 and 4 for 24-48 h in a dose-dependent manner.