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Submitted
October 17, 2016
Accepted
October 17, 2016
Published
October 17, 2016
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Abstract

Telah dilakukan sintesis turunan senyawa kalkon tersubstitusi gugus nitro dan hidroksi melalui reaksi kondensasi Claisen Schmidt. Tujuan penelitian ini adalah untuk mensintesis senyawa kalkon yang tersubstitusi gugus hirdoksi dan nitro dalam medium basa, dan mempelajari pengaruh gugus tersebut dalam reaksi kondendasi. Kalkon 1 disintesis dari 4-nitroasetofenon dan vanilin menggunakan katalis NaOH 60% (b/v dalam akuades) melalui pengadukan selama 24 jam. Kalkon 2 didapatkan dari reaksi antara 4-nitroasetofenon dan veratraldehida dengan katalis NaOH 15% selama 4 jam, sedangkan kalkon 3 disintesis dari 4-nitroasetofenon dan 6-nitroveratraldehida dalam 5% NaOH 10 tetes. Produk hasil sintesis dikarakterisasi dengan FTIR, GC-MS dan 1H-NMR.

Hasil penelitian menunjukkan bahwa senyawa kalkon telah berhasil disintesis dengan rendemen berturut-turut sebesar 16,80; 75,83; dan 44,11 % dalam medium basa. Dari penelitian ini, dapat disimpulkan bahwa adanya gugus hidroksi dari sumber aldehida aromatik pada kalkon 1 menghambat terjadinya reaksi, sedangkan gugus nitro yang terikat pada aldehida aromatik menjadi kendala pada reaksi kalkon 3 karena sifatnya yang sensitif terhadap cahaya.

Keywords

kalkon kondensasi Claisen Schmidt 4-nitroasetofenon 6-nitroveratraldehida

Article Details

How to Cite
Fauzi’ah, L., & Wahyuningsih, T. D. (2016). Synthesis of Chalcones Substituted with Nitro and Hydroxyl Group in Alkaline Medium. EKSAKTA: Journal of Sciences and Data Analysis, 16(2), 103–114. https://doi.org/10.20885/eksakta.vol16.iss2.art5
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References

  1. Arty, I.S., Rohmawati, D., 2014, Optimization of Condensation Reaction Time Between Vanillin and p-Nitroacetophenone in Acid Catalysts, J.Sains Dasar 3(1): 34-38.
  2. Choudhary, A.N. dan Juyal, V., 2011, Synthesis of Chalcone and Their Derivatives as Antimicrobial Agents, Int. J. Pharm. Pharm. Sci., 3-6.
  3. Dias, T.A., Duarte, L.C., Lima, C.F. and Proenca, M.F., 2013, Superior Anticancer Activity of Halogenated Chalcones and Flavonols Over the Natural Flavonols Quercetin, Eur. J. Med. Chem., 65, 500-10.
  4. Hammuda, A., Shalaby, R., Rovida, S., Edmondson, D.E., Binda, C., Khalil, A., 2016, Design and Synthesis of Novel Chalcones as Potent Selective Monoamine Oxidase-B Inhibitors, Eur. J. Med. Chem., doi:10.1016/j.ejmech.2016.02.038.
  5. Hans, R.H., Guantai, E.M., Lategan, C., Smith, P.J., Wan, B., Franzblau, S.G., Gut, J., Rosethal, P.J., Chibale, K., 2009, Synthesis, Antimalarial and Antitubercular Activity of Acetylenic Chalcones, Bioorg. Med. Chem. Lett. 20: 942-944.
  6. Jagadeesh, M., Lavanya, M., Babu, B.H., Hong, K., Ma, R., Kim, J., and Kim. T.K., 2015, Synthesis and Detailed Spectroscopic Characterization of Various Hydroxy-functionalized Fluorescent Chalcones: A Combined Experimental and Theoretical Study, Spectrochim Acta A Mol Biomol Spectrosc., 150: 557-564, http://dx.doi.org/10.1016/j.saa.2015.05.085.
  7. Janaki, P., Sekar, K.G., Thirunarayanan, G., 2012, Synthesis, Spectral Correlation and Insect Antifeedant Activities of Some 2-Benzimidazole Chalcones, J. Saudi Chem. Soc. 20; 58-68, http://dx.doi.org/10.1016/j.jscs.2012.11.013.
  8. Lawrence, N.J., Patterson, R.P., Ooi, L.L., Cook, D., and Ducki, S., 2006, Effect of Alfa-Substitutions on Structure and Biological Activity of Anticancer Chalcones, Med. Chem. Lett. (16): 5844-48.
  9. Mahapatra, D.K. dan Bharti, S.K., 2016, Therapeutic Potential of Chalcones as Cardiovascular Agents, Life Sci.148: 154–172, http://dx.doi.org/10.1016/j.lfs.2016.02.048.
  10. Nowakowska, Z., 2007, A Review of Anti-infective and Anti-inflammatory Chalcones, Eur. J. Med. Chem. 42: 125-137, doi:10.1016/j.ejmech.2006.09.019.
  11. Singh, P., Anand, A., and Kumar, V., 2014, Recent Developments in Biological Activities of Chalcones: A Mini Review, Eur. J. Med. Chem. 85: 758-777, http://dx.doi.org/10.1016/j.ejmech.2014.08.033.
  12. Susanti, E. dan Redjeki, T., 2011, Synthesis of 2',4'-Dihydroxy-3,4-Dimethoxychalcone from Vanillin by Claisen-Schmidt Condensation, Prosiding Seminar Kimia dan Pendidikan Kimia UNS, 7 Mei 2011, Solo.
  13. Wan, M., Xu, L., Hua L., Li, A., Li, S., Lu, W., Pang, Y., Cao, C., Liu, X., and Jiao, P., 2014, Synthesis and Evaluation of Novel Isoxazolyl Chalcones as Potential Anticancer Agents, Bioorg. Chem.(54): 38–43, http://dx.doi.org/10.1016/j.bioorg.2014.03.004.
  14. Vanangamudi, G., Subramanian, M., Jayanthi, P., Arulkumaran, R., Kamalakkannan, D. and Thirunarayanan, G., 2011, IR and NMR Spectral Studies of Some 2-Hydroxy-1-Naphthyl Chalcones: Assessment of Substituent Effects, Arabian J. Chem., 1-8.