In vitro study of antifungal properties of DHPM 1, 2 and 3 were evaluated against two selective fungi Aspergillus niger, Penicillium chrysogenum and the results are summarized in table It was unfortunate to note that DHPM-3 which contain electron deficient 4-chloro phenyl ring, did not show any antifungal activities against either of these two fungi Aspergillus niger and Penicillium chrysogenum even at ppm concentration.
Comparative view of antifungal properties of compound-1 and 2 are shown by graphical representation in figure Table 2: Anti-Fungal Properties. Figure 1: Comparison of antibacterial activities of compound-1 and 2. Figure 2: Comparison of antifungal activities of compound-1 and 2.
It was observed that biginelli reaction with electron rich aromatic aldehyde requires longer time for completion than with electron deficient aromatic aldehyde at room temperature in lime juice medium.
After in vitro study of their antimicrobial properties against four selective pathogenic microorganisms namely Escherichia coli, Salmonella typhimurium, Aspergillus niger and Penicillium chrysogenum, it was concluded that DHPM containing electron rich phenyl ring is more effective antibacterial agent whereas DHPM containing neutral phenyl ring is more efficient antifungal agent. DHPM which contains electron deficient phenyl ring shows neither antibacterial nor antifungal properties against these four selective microorganisms.
However the scope of this conclusion is limited to only against these selective microorganisms under specific experimental condition as mentioned earlier.
J Med Chem ; 3: Bioorg Med Chem ; J Med Chem ; Oriental J Chem ; J Org Chem ; 1: Kaushik, Molecules. Muchchintala, H. Sang, K. Ketack, Y. Jung, Bull. S Falsone, C. Kappe, Arkivoc 2, Shanmugam, P. Perumal, Tetrahedron 62, Ko, C. Yao, Tetrahedron 62, Y Fu, Y. Yuan, Z.
Cao, S. Wang, C. Peppe, Tetrahedron 58, Jin, H. Xing, X. Li, T. Li, Synth. Ma, C. Qian, L. Wang, M. Yang, J. Shaabani, A. Bazgir, F. Teimouri, Tetrahedron Lett. Borse, M. Patil, N. Patil, R. Article ID , 1 Ramalingan, Y. Kwak, Tetrahedron 64, Kumar, P. Sharma, K. Kapoor, M. Hundal, Tetrahedron 64, Sweet, J. Fissekis, J. Kappe, A, J.
Cepanec, M. Litvic, M. Filipan-Litvic, I. Grungold, Tetrahedron 63, Litvic, I. Vecenaj, Z. Ladisic, M. Lovric, V. Vinkovic, M. Filipan-Litvic, Tetrahedron 66, Besoluk, M. Kukukislamoglu, M. Zengin, M. Arsalan, M. With progress of the reaction a solid started to deposit. The solid was taken out carefully with a spatula or spoon in a conical flask.
Ia: 5- Ethoxy carbonyl - 4 - phenyl - 6-methyl - 3,4 - dihydropyrimidin-2 1H one: m. IIa: 5- Ethoxy carbonyl - 4 - phenyl - 6-methyl - 3,4 - dihydropyrimidin-2 1H thione: m. IIIa: 5- Ethoxy carbonyl - 4, 6- dimethyl- 3, 4 - dihydropyrimidin-2 1H one: m. Chemical shifts are reported in parts per million ppm from tetramethylsilane with tetramethylsilane as the internal standard. Data reported are as follows: chemical shift, multiplicity as singlet s , doublet d , triplet t , quartet q , broad singlet br s and multiplet m , and coupling constants Hz.
Combustion analyses were performed on a Perkin-Elmer II analyzer. The progress of the reactions was monitored by thin layer chromatography using F silica gel pre-coated sheets Merck, India. Column chromatography was performed on silica gel to mesh.
Scheme 1 Synthetic scheme for the preparation of compounds 3a to 3 l. General method for the preparation of compounds 1a to 1d A solution of arylaldehyde 0. Progress of the reaction was monitored by thin layer chromatography TLC using hexane:ethyl acetate as mobile phase. Then, the reaction mixture was cooled to room temperature, poured into ice-cold water to mL and stirred for 15 min.
The solid precipitate obtained was filtered, washed with ice-cold water and recrystallized with absolute alcohol to afford white solid crystals with a quantitative yield [ 10 ]. Melting point Mp.
Progress of the reaction was monitored by TLC using chloroform:methanol as mobile phase. The reaction mixture was cooled and concentrated under vacuum to remove methanol.
The ethyl acetate layer was separated, pooled over anhydrous sodium sulfate and evaporated under vacuum to give the crude acid.The product of this novel one-pot, three components synthesis that precipitated on cooling of the reaction mixture was identified as 3,4-dihydropyrimidin-2 1H one. Grungold, Tetrahedron 63, Pei, J. In addition, the molecular mass and Xime bangalore admissions essay physicochemical properties were able to understand the structural synthesis relationship of the scaffold. Maurya, J. Zengin, M. Shishkin, G. Texture, M. Uray, P. Taffy, Chem. The impregnated obscures were placed on the medium suitably spaced anywhere, 0 and the plates were sold at 32 C for 24 h. Directly the derivative of this policy is limited to only against these life microorganisms under specific experimental condition as mentioned earlier.
A substantial amount of decarboxylated product was formed during hydrolysis, similar to the earlier reports [ 7 ]. Surrey, A. General procedure for the synthesis of 3,4-dihydropyriinidin-2 1H -ones thiones A mixture of aldehyde 1. For this purpose, various parameters such as molar ratio of reactants, catalyst and reaction temperature were optimized. The extract was purified by column chromatography using chloroform:methanol and silica gel to mesh as stationary phase to afford the desired product [ 19 , 20 ].
Schreiber, T. It was observed that the electronic factor of the phenyl ring of DHPM has significant influence on their antimicrobial properties. Solid catalysts are harmless to the environment due to safety, no corrosion and reduction of the amount of waste residuals. Sharma, K. Molecular docking study gave a clear insight into the structural activity relationship of the compounds in comparison with monastrol.
Ray, F. Fissekis, J. A: Chem. Then a comparative study of antifungal and antibacterial activity of the synthesized compounds will help us to gain insight into the effect of electronic factor on their antimicrobial properties. Test compounds were prepared just prior to the experiment in 0. Table 1 shows the effect of catalyst concentration on the reaction of benzaldehyde, ethylacetoacetate and urea.
IC50 values of the synthesized compounds against the proliferation of human hepatocellular carcinoma and human epithelial carcinoma cell lines were determined through MTT assay.
Gougoutas, M. Ketack, Y. Biginelli reaction is acid catalyzed cyclo-condensation reaction of ethyl acetoacetate, benzaldehyde and urea illustrated below Fig. Li, Z. Test compounds were prepared just prior to the experiment in 0. Keshari, Tetrahedron Lett.
Banik, A. Malley, Heterocycles 26, This was due to over an obvious concentration, there have an excess of catalyst sites beyond what is actually required by the reactant substrates, and the additional catalyst does not increase the rate of the reaction. Atwal, A.
Nasr-Esfahani, S. Following our interest in producing 3,4-dihydropyrimidine-2 1H -ones 20, a study to revisit this reaction in a parallel combinatorial fashion using Co NO3 2. The solid precipitate obtained was filtered, washed with ice-cold water and recrystallized with absolute alcohol to afford white solid crystals with a quantitative yield [ 10 ]. Liu, C. The solution was heated to dissolve the ingredients completely after which the media was autoclaved. Qian, L.