Synthesis of Nitrogen-Containing Chalcone Via One-Pot Three-Component Reaction . part ii
Keywords:Chalcone, 3-Hydroxybenzaldehyde, 4-Methoxyacetophenone, Aminomethylation, Formaldehyde, N-Methylpiperazine.
The compound 3-Hydroxy-4'-methoxychalcone (1) was prepared by reacting 3-hydroxybenzaldehyde with 4-methoxyacetophenone.
The aminomethylation of this chalcone was accomplished by reaction with formaldehyde and N-methylpiperazine in dry acetonitrile to Obtain 3-hydroxy-4'-methoxy-4-(N-methyl-piperazinomethyl) chalcone (2) and 3-hydroxy-4'-methoxy-2,4-bis-(N-methylpiperazinomethyl)chalcone(3). The products were purified by column and thin layer chromatography and were identified along with their intermediates by spectroscopic methods: UV, IR, NMR and mass spectrometry.
 Abraham G., et Al., Synthesis and anti-inflammatory activity of three nitro chalcones; J. Bioorg and Med. Chem. Lett. 2003; 23:5519.
 Afaf, H., Fahmy, H. H. and Ali, A., Synthesis and An-timicrobial Activity of Some New Benzimidazole De-rivatives, Molecules, 2000; 5: 1429. http://dx.doi.org/10.3390/51201429.
 Dimmock, J. R. and Kamar, P., Anticancer and cyto-toxic properties of Mannich basses, Curr. Med., Chem. 1997; 4:1.
 Ebru, M., Halise, I. G. and Cuvit, K., Synthesis of 1-Aryl-3-phenethylamino-1- propanone Hydrochlorides as Possible Potent Cytotoxic Agents, Molecules, 2007; 12: 2579 . http://dx.doi.org/10.3390/12122579.
 Herencia, F. et al., Synthesis and anti-inflammatory activity of chalcone derivatives, J. Bioorg. Med. Chem. Lett.1998; 8: 1169. http://dx.doi.org/10.1016/S0960-894X (98)00179-6.
 Ina-Gull, H. et.al., Cytotoxic activities of mono and bis Mannich bases derived from acetophenone against Renca and Jurkat cell, pharmaceutica Acta Helvetiae, 2000; 74:393.
 Janathan, R. et al., 4-(beta-Arylvinyl)-3-(beta-arylvinylketo)-1-ethyl-4-piperidinols and related com-pounds: a novel class of cytotoxic and anticancer agents, J. Med. Chem., 1998; 41: 4012. http://dx.doi.org/10.1021/jm9801455.
 Jontathan, R. et al., Cytoxic Evaluation of Some 3,5-Diarylidene-4-piperidones and Various Related Quater-nary Ammonium Compounds and Analogs, Eur. J. Med. Chem., 2002; 37: 35.
 Ko, H. H., Tsao, I. T., Wang, J. P., Lin, C. N., Struc-ture-Activity Relationship Studies on Chalcone Deriv-atives:The Potent Inhibition of Chemical Mediator Release. Bioorg. Med. Chem., 11, 105-111, J. Bioorg. Med., 2003; 11:105. http://dx.doi.org/10.1016/S0968-0896 (02)00312-7.
 Li, R. et al., In Vitro antimalarial activity of chalcones and their derivatives, J. Med. Chem., 1995; 38: 5031. http://dx.doi.org/10.1021/jm00026a010.
 Lin, Y. M. ET. al., Chalcones and flavonoids as anti-tuberculosis agents, J. Bioorg.Med. Chem., 2002; 10.
 Lopez, S. N. et al., in vitro antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall, J. Bioorg. Med. Chem., 2001; 9: 1999. http://dx.doi.org/10.1016/S0968-0896(01)00116-X.
 Mutlu, D. A. and Vnsal, C., Synthesis of Some Novel Mannich Bases Derived From Allomaltol and Evaluation of Their Anticonvulsant Activities, Hacettepe University Journal of The Faculty of Pharmacy, 2007; 27(1): 1.
 Nabil, M. et al., Synthesis of some 6-(alkylamino) methylhexahydro-5-aryl and aralkyl-4, 7-methanoindan -5-ols and certain of their propionate eater as analgesics, Journal of Islamic Acedemy of Science, 1993; 6(2): 99 .
 Ozan, R., Zuhal, O., Unsal, C., Butent, G. and Abdullah, A. B., Argnei-Forch., Synthesis of and pharmacological studies on the antidepressant and anticonvulsant activities of some 1,3,5-trisubstituted pyrazolines, j. rug Res., 2005; 55 (8):431.
 Parmer, V. S. et al., In vitro antimalarial activity of chalcones and their derivatives, J. Bioorg. Med. Chem., 2003; 11: 913.
 Robert, M. et al., Synthesis of Abyssinone II and related compounds as potential chemopreventive agents, Eur. J. Med. Chem.,2006; 41: 263 . http://dx.doi.org/10.1016/j.ejmech.2005.09.008.
 Stephen, J., Judith, J. and Leslie, M., Synthesis and Antimalarial Effects of 4-(7- Chloro-4-quinolinyl) ami-no]-2-[(diet hy1amino) met hyl]-6-alkylphenols and their N'- Oxides J. Med. Chem., 1987; 30: 906. http://dx.doi.org/10.1021/jm00388a027.
 Tamas, L. et al., Synthesis and antibacterial effect of fused Mannich ketones, Eur. J. Med. Chem., 2002; 37: 803. http://dx.doi.org/10.1016/S0223-5234(02)01404-6.