A facile four-component sequential protocol in the expedient synthesis of novel 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones in water and their antitubercular evaluation

作者：Gunasekaran Pethaiah; Perumal Subbu^*; Yogeeswari Perumal; Sriram Dharmarajan

来源：European Journal of Medicinal Chemistry, 2011, 46(9): 4530-4536.

DOI：10.1016/j.ejmech.2011.07.029

• Multi-component
• Sequential
• Methyl acetatoacetate
• Phenylhydrazines
• beta-naphthol
• Pyrazolones
• Antimycobacterial activity

A series of 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones has been synthesized by one-pot, four-component sequential reactions of phenylhydrazine, methyl acetoacetate, aromatic aldehydes and beta-naphthol in the presence of p-toluenesulphonic acid in water in good yields. These 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones were screened for in-vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among the 15 compounds screened, 4-[(2,4-dichlorophenyl)(2-hydroxy-1-naphthyl)methyl]-2-(4-fluorophenyl)-5-methyl-2,3-dihydro-1H-3-pyrazolone displays the maximum potency with a minimum inhibitory concentration (MIC) of 1.6 mu M against MTB, being 2.94 and 4.75 times more active than ciprofloxacin and ethambutol respectively.

• 出版日期2011-9