Sintesis Senyawa Dihidropirimidinon Melalui Reaksi Siklokondensasi Menggunakan Katalis Larutan Asam Jawa

Fachri Hakim*  -  Program Studi Kimia, Fakultas Sains dan Teknologi, UIN Walisongo Semarang, Indonesia
Irfan Fitriadi  -  Program Studi Pendidikan Kimia Program Pascasarjana, Universitas Negeri Semarang, Indonesia
Supartono Supartono  -  Program Studi Kimia, Universitas Negeri Semarang, Indonesia

(*) Corresponding Author
Tujuan penelitian ini adalah untuk mensintesis senyawa dihidropirimidinon melalui reaksi siklokondensasi Biginelli menggunakan katalis larutan asam jawa. Senyawa dihidropirimidinon  merupakan  hasil  reaksi  siklokondensasi biginelli  dari aldehid,  etil  asetoasetat,  dan  urea  atau  tiourea yang memiliki  aktivitas  biologis  dan  bersifat antimikroba.  Reaksi ini merupakan reaksi kondensasi antara benzaldehid 6, 2-indanon 2 dan urea 7 dalam suasana asam Identifikasi  senyawa dihidropirimidinon  dilakukan  dengan    uji  FT-IR  dan  uji  GC-MS. Dari hasil penelitian sintesis senyawa dihidropirimidinon dengan katalis larutan asam jawa membuktikan bahwa larutan asam jawa dapat digunakan sebagai katalis sintesis senyawa dihidropirimidinon melalui reaksi siklokondensasi Biginelli. Sehingga dapat digunakan untuk mengatasi wabah penyakit infeksi.

Keywords: Siklokondensasi; Larutan Asam Jawa; Dihidropirimidinon

  1. Amini, M. M., A. Shaabani and A. Bazgir. 2006. Tangstophoosporic Acid (H3PW12O40): An efficient Eco-friendly Catalyst for the One-pot Synthesis of Dihydropyrimidin-2-(1H)-ones. Catalysis Communications 7: 843-847.
  2. Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A., and O'Reilly, B. C. ,1991, 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic Acid Esters as Orally Effective Antihypertensive Agents. J. Med. Chem. 34, 806
  3. Dolle, R. E., and Nelson, K. H., 1999, Comprehensive Survey of Combinatorial Library Synthesis J. Comb. Chem. 1, 235
  4. Domling, A., 2002, Curr. Opin. Chem. Biol. 6, 306, cit., Bose, D. S., Sudharshan, M., Chavhan, S.W., 2005, New Protocol for Biginelli Reaction-a Practical Synthesis of Monastrol, Arkivoc, 3, 587
  5. Funke I and MF Melzig, 2006.Traditionally used plants in diabetes therapy-phytotherapeutics as inhibitors of a-amylase activity. Braz J Pharmacogn, 16(1): 1-5
  6. Gordon, E. M., Gallop, M. A., and Patel, D. V., 1996, Strategy and Tactics in Combinatorial Organic Synthesis. Applications to Drug Discovery, Acc. Chem. Ret. 29, 144.
  7. Hurst, E. W., and Hull, R., 1961, J. Med. Pharm. Chem. 3, 215.
  8. Jauk, B., Pernat, T., and Kappe, C. O., 2000, Design and Synthesis of a Conformationally Rigid Mimic ... Calcium Channel Modulator SQ32,926, Molecules 5, 227.
  9. Kape, C. O., 1998, 4-Aryldihydropyrimidines via Biginelli Condensations: Aza Analogs of Nifedipine-Type Calcium Channel Modulators, Molecules 3, 1.
  10. Kappe, C. O.,1993, 100 Years of The Biginelli Dihydropyrimidine Synthesis, Tetrahedron 49, 6937 Kappe, C. O., 2000, Recent Advances in the Biginelli Dihydropyrimidine Synthesis. New. Tricks From an Old Dog, Acc. Chem. Res. 33, 879.
  11. Kato, T.: Jpn. Kokay Koho 59 190,974: (CA 102:132067), 1984.
  12. Mayer, T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. I., and Mitchison, T. J., 1999, Small Molecule Inhibitor of Mitotic Spindle Bipolarity Indetified in a Phenotype- Based Screen, Science 286, 971.
  13. Patil, A. D., kumar, N. V., Kokke, W. C., Bean, M. F., Freyer, A. J., Debrossi, C., Mai, S., Truneh, Fraulkner, D. J., Carte, B., Breen, A. L., Hertzberg, R. P., Johnson, R. K., Westley, J. W., and Potts, B. C. M., 1995 Novel Alkaloids from the Sponge Batzella sp.: Inhibitors of HIV gp 120-human CD4 Binding, J. Org. Chem. 60, 1182.
  14. Rovnyak, G. C., Atwal, K S., Hedberg, A., Kimball, S. D., Moreland, S., Gougoutas, J. Z., O'Reilly, C., Schwartz, J., and Malley, M. F., 1992, Basic 3-Substituted-4-aryl-1,4- dihydropyrimidine-5-carboxylic Acid Esters. Potent Antihypertensive Agents, J. Med. Chem. 35, 3254, 1992.
  15. Russowsky, D., Lopes, F. A., Da Silva, V. S. S., Canto, K F. S., D'Oca, M. G. M., and Godoi, M. N., 2004, Multicomponent Biginelli's Synthesis of 3,4-dihydropyrimidin-2(1K)-ones Promoted by SnCR2H2O, J. Braz.. Chem. soc. 15, 2
  16. Thompson, L. A., and Ellman, J. A., 1996, Synthesis and Applications of Small Molecule Libraries, Chem. Rev. 96, 555.
  17. Weber, L., 2002, Multicomponent Biginelli's synthesis of 3,4-dihydropyrimidin-2-(/H)-ones promoted by SnCb.2H2O. Drug. Disc. Today 7, 143.
  18. William JT, 2006. Fruit for the future 1, Revised edition: Tamarind (Tamarindus indicaL.) Dalam: William JT, RW Smith N Haq & Dunsiger (eds). International Center for Underutilised crops, University of Southampton, Southampton, 2-32.

Open Access Copyright (c) 2018 Walisongo Journal of Chemistry
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.

WJC: Walisongo Journal of Chemistry
Published by the Department of Chemistry
Faculty of Science and Technology
Universitas Islam Negeri Walisongo Semarang
Jl Prof. Dr. Hamka Kampus III Ngaliyan Semarang 50185
Website: https://journal.walisongo.ac.id/index.php/wjc
Email: wjc@walisongo.ac.id  wjc@walisongo.ac.id

ISSN: 2549-385X (Print)
ISSN: 2621-5985 (Online)




 

apps