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Volumn 4, Issue 2, 2007, Pages 144-148

Design, synthesis and biological testing of cyclohexenone derivatives of combretastatin-A4

Author keywords

Anticancer; Combretastatin A4; Cyclohexenone; Cytotoxicity; Synthesis; Tubulin

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; 6 (ETHOXYCARBONYL) 2 CYCLOHEXENONE DERIVATIVE; COMBRETASTATIN A4; UNCLASSIFIED DRUG;

EID: 33846324308     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018007779422442     Document Type: Article
Times cited : (27)

References (29)
  • 22
    • 33846283150 scopus 로고    scopus 로고
    • A typical synthesis is described. The chalcone (e.g. 6, ∼150 mg, 1 molar equiv, was dissolved in EtOH (4 mL, Ethyl acetoacetate (1.1 molar equiv, and barium hydroxide (0.1 molar equiv, were added and the solution was stirred under reflux for 6-30 h. The solvents were removed under vacuum and the residue dissolved in CH2Cl2 (40 mL) and washed with water (3 x 20 mL, The organic layer was dried (Na2SO4) and evaporated to dryness. If required the product was purified with silica gel flash-column chromatography using a gradient solvent system (100-60:0-40% v/v Petroleum ether/EtOAC) to yield the pure products. 6-Ethoxycarbonyl-5, 3′-hydroxy-4′-methoxyphenyl)-3-(3″,4″, 5″-trimethoxyphenyl)-2-cyclohexenone (7, Refluxed for 30 h to yield an orange-brown semi-solid (179 mg, 81, Rf, 0.43 (60:40% v/v, Pet. Ether/EtOAc, 1H NMR (CDCl3) δ 1.11 t, J
    • +, 100%).
  • 28
    • 33846325196 scopus 로고    scopus 로고
    • A-10 cells, aortic smooth muscle cell line) were obtained from the American Type Culture Collection, Manassas, VA, The cells were grown in Basal Medium Eagle containing Earle's salts, gentamycin sulfate (50 μg mL -1) and fetal bovine serum 10, Cells were plated onto glass coverslips in 24-well plates, allowed to adhere, and grown for at least 24 h. The cells were exposed to the required compound or DMSO vehicle for 18 h, fixed and the microtubules and DNA visualized by indirect immunofluorescence techniques, as previously described [14, 15, A range of concentrations of each compound was evaluated, concentrations that caused no microtubule effects to those that caused total microtubule loss, with several intermediate points, The percent microtubule loss was estimated for each concentration tested, and the results of three experiments were averaged. The percentage of depolymerization was plotted against compound concentration and the linear potion of the line fit u
    • 50 values were calculated from the linear equations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.