Synthesis, Spectroscopy and Electrochemistry of New 3-(5-Aryl-4,5-Dihydro-1H-Pyrazol-3-yl)-4-Hydroxy-2H-Chromene-2-One 4, 5 as a Novel Class of Potential Antibacterial and Antioxidant Derivatives  

作　　者：Abdullah Sulaiman Al-Ayed 

机构地区：[1]不详

出　　处：《International Journal of Organic Chemistry》2011年第3期87-96,共10页有机化学国际期刊（英文）

摘　　要：3-((2E)-3(aryl)prop-2-enoyl)-2H-chromen-2-one 3 was synthesized from 4-hydroxy coumarin by refluxing 3-acetyl-4-hydroxy coumarin with aromatic aldehydes in chloroform in the presence of a catalytic amount of piperidine. 3 was converted to pyrazoles 4, 5 by treatment with hydrazine and phenylhydrazine in toluene, respectively. The structures of the new compounds were confirmed by elemental analysis, IR, and multinuclear/multidimensional NMR spectroscopy (1H, 13C-NMR, NOESY, HMBC) which allowed us to assign the complete network of proton and carbon atoms. All the compounds exhibited one quasireversible redox process. All the newly synthesized compounds were screened for their antibacterial and antioxidant activities. Antimicrobial studies revealed that 3-(5-(2,5-dimethylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-4- hydroxy-2H-chromene-2-one 5c showed significant antibacterial activity against Escherichia coli and Pseudomonas Aeruginosa 27853. Furthermore, 3-(5-(aryl)-4,5-dihydro-1H-pyrazol-3-yl)-4-hydroxy-2H-chromene- 2-ones 4, 5 showed antioxidant activities of different extents with respect to individual compounds as well as to the antioxidant methods. The 3-(5-(phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-4-hydroxy-2H-chromene-2-ones 4a was found to be the most active antioxidant in the series and more active than trolox which makes the investigated complexes a new promising class of antibacterial compounds.3-((2E)-3(aryl)prop-2-enoyl)-2H-chromen-2-one 3 was synthesized from 4-hydroxy coumarin by refluxing 3-acetyl-4-hydroxy coumarin with aromatic aldehydes in chloroform in the presence of a catalytic amount of piperidine. 3 was converted to pyrazoles 4, 5 by treatment with hydrazine and phenylhydrazine in toluene, respectively. The structures of the new compounds were confirmed by elemental analysis, IR, and multinuclear/multidimensional NMR spectroscopy (1H, 13C-NMR, NOESY, HMBC) which allowed us to assign the complete network of proton and carbon atoms. All the compounds exhibited one quasireversible redox process. All the newly synthesized compounds were screened for their antibacterial and antioxidant activities. Antimicrobial studies revealed that 3-(5-(2,5-dimethylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-4- hydroxy-2H-chromene-2-one 5c showed significant antibacterial activity against Escherichia coli and Pseudomonas Aeruginosa 27853. Furthermore, 3-(5-(aryl)-4,5-dihydro-1H-pyrazol-3-yl)-4-hydroxy-2H-chromene- 2-ones 4, 5 showed antioxidant activities of different extents with respect to individual compounds as well as to the antioxidant methods. The 3-(5-(phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-4-hydroxy-2H-chromene-2-ones 4a was found to be the most active antioxidant in the series and more active than trolox which makes the investigated complexes a new promising class of antibacterial compounds.

关 键 词：4-HYDROXYCOUMARIN Pyrazole ANTIBACTERIAL ACTIVITY Antioxydant ACTIVITY 

分 类 号：O6[理学—化学]