Chawla Rakesh, Sahoo Ujjwal, Arora Anshu, Sharma Prabodh Chander, Radhakrishnan Vijayaraj
Department of Pharmaceutical Chemistry, S.D. College of Pharmacy, Barnala-148 101, India.
Acta Pol Pharm. 2010 Jan-Feb;67(1):55-61.
Some new 3-(4-phenyl)-5-phenyl-4,5-dihydropyrazol-1-ylmethanones and 3-substituted phenyl-5-substituted phenyl-4,5-dihydro-pyrazole-1-carbothioamides have been synthesized employing microwave techniques and evaluated for antimicrobial activity. Substituted acetophenones (1) were reacted with appropriately substituted benzaldehydes (2) in the presence of ethanol to furnish substituted chalcones (3a-f). These chalcones were further treated with isonicotinic acid hydrazide (INH) to afford substituted 3-(4-phenyl)-5-phenyl-4,5-dihydropyrazol-1-ylmethanones (4a-f). Reaction of these chalcones with thiosemicarbazide yielded substituted 3,5-diphenyl-4,5-dihydro-1H-pyrazole-1-carbothioamides (5a-f). The structures of newly synthesized compounds (4a-f) and (5a-f) have been confirmed by suitable spectroscopic techniques such as IR and 1H NMR. All the compounds were screened for their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa and for antifungal activity against Candida albicans and Aspergillus niger The compounds exhibited moderate antibacterial and good antifungal activities. Compound 4b and 4d showed significant antifungal activity against A. niger and C. albicans, respectively.
一些新型的3-(4-苯基)-5-苯基-4,5-二氢吡唑-1-基甲酮和3-取代苯基-5-取代苯基-4,5-二氢吡唑-1-碳硫酰胺已采用微波技术合成,并对其抗菌活性进行了评估。取代苯乙酮(1)在乙醇存在下与适当取代的苯甲醛(2)反应,得到取代查耳酮(3a-f)。这些查耳酮再用异烟肼(INH)处理,得到取代的3-(4-苯基)-5-苯基-4,5-二氢吡唑-1-基甲酮(4a-f)。这些查耳酮与硫代氨基脲反应,生成取代的3,5-二苯基-4,5-二氢-1H-吡唑-1-碳硫酰胺(5a-f)。新合成化合物(4a-f)和(5a-f)的结构已通过红外光谱和1H核磁共振等合适的光谱技术得到证实。所有化合物均针对金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌和铜绿假单胞菌进行了抗菌活性筛选,并针对白色念珠菌和黑曲霉进行了抗真菌活性筛选。这些化合物表现出中等的抗菌活性和良好的抗真菌活性。化合物4b和4d分别对黑曲霉和白色念珠菌表现出显著的抗真菌活性。