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Vol. 30 No. 3 (2018): Vol 30 Issue 3

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Synthesis and Biological Activities of New Fused Pyrimidine Compound

https://doi.org/10.14233/ajchem.2018.21093
Hamid H. Mohammed
Department of Chemistry, College of Science, Al-Mustansiryah University, Baghdad, Iraq
Zaizafoone N. Nasif
Department of Chemistry, College of Science, Al-Mustansiryah University, Baghdad, Iraq
Zainab N. Mageed
Unit of Polymer Research, College of Science, Al-Mustansiryah University, Baghdad, Iraq
S. Ahmed
Department of Chemistry, College of Science, Al-Mustansiryah University, Baghdad, Iraq

Corresponding Author(s) : Hamid H. Mohammed

hamidhashim@uomustansiriyah.edu.iq; hammed_sugar@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 3 (2018): Vol 30 Issue 3

Abstract

In this work, a new fused pyrimidine derivatives {5-(4-chlorophenyl)-4-oxo-3,5-dihydro-4H-chromeno[ 2,3-d]pyrimidin-8-yl formate)} was prepared from chromene compound {(2-amino-4-(4-(dimethylamino)phenyl)-5-oxo-4,5-dihydropyran[3,2-c]chromene-3-carbonitrile} with formic acid in presence of POCl3 and identified by FT-IR and 1H NMR spectra. The pyrimidine compounds have medicinal and biological activities. Therefore the effect of these compounds was studied on human serum acetylthiocholine esterase activity. The results concluded that the greater inhibition percent was found at concentrations (10-2) M for each compounds chromene and pyrimidine respectively and indicated that Km varied from higher, lesser or the same in the presence of chromene and pyrimidine compared with non-inhibiting system. The maximum and minimum inhibitor concentrations of chromene appeared mix inhibition during enzymatic reaction, in contrast pyrimidine does not compute with substrate on the active site of enzyme (noncompetitive and uncompetitive inhibition). The Vmax value for control sample was higher than in inhibited samples, The biochemical tests revealed that Ki (the binding affinity of the inhibitor) for chromene and pyrimidine compounds are higher at 10-2 M (1.5 × 10-3, 1.11 × 10-3).

Keywords

Pyrimidine Chromene Biological activities Acetyl thiocholine esterase Inhibitors Linewer-burk equation
Mohammed, H. H., Nasif, Z. N., Mageed, Z. N., & Ahmed, S. (2018). Synthesis and Biological Activities of New Fused Pyrimidine Compound. Asian Journal of Chemistry, 30(3), 661–666. https://doi.org/10.14233/ajchem.2018.21093
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References
  1. T. Sasada, F. Kobayashi, N. Sakai and T. Konakahara, Org. Lett., 11, 2161 (2009); https://doi.org/10.1021/ol900382j.
  2. R.F. Lloyd, C.G. Skinner and W. Shive, Can. J. Chem., 45, 2213 (1967); https://doi.org/10.1139/v67-357.
  3. V.P. Litvinov, ed.: A.R. Katritzky, The Chemistry of Thienopyrimidines, In: Advances in Heterocyclic Chemistry, Elsevier, vol. 92, p. 83-126 (2006).
  4. M. Amir, S.A. Javed and H. Kumar, Indian J. Pharm. Sci., 69, 337 (2007); https://doi.org/10.4103/0250-474X.34540.
  5. R.B. Patel, P.S. Desai, K.R. Desai and K. Chikhalia, Indian J. Chem., 45B, 773 (2006).
  6. A.E.-Galil E. Amr, N.M. Sabry and M.M. Abdulla, Monatsh. Chem., 138, 699 (2007); https://doi.org/10.1007/s00706-007-0651-0.
  7. N. Fujiwara, T. Nakajima, Y. Ueda, H. Fujita and H. Kawakami, Bioorg. Med. Chem., 16, 9804 (2008); https://doi.org/10.1016/j.bmc.2008.09.059.
  8. L. Ballell, R.A. Field, G.A.C. Chung and R.J. Young, Bioorg. Med. Chem. Lett., 17, 1736 (2007); https://doi.org/10.1016/j.bmcl.2006.12.066.
  9. E. Wagner, K. Al-Kadasi, M. Zimecki and W. Sawka-Dobrowolska, Eur. J. Med. Chem., 43, 2498 (2008); https://doi.org/10.1016/j.ejmech.2008.01.035.
  10. C. Jean-Damien, B. David, K. Ronald, G. Julian, L. Pan and D. Robert, PCT Int. Appl., 22,608 (2002).
  11. K. Gorlitzer, S. Herbig and R.D. Walter, Pharmazie, 52, 670 (1997).
  12. I.V. Ukrainets, I.A. Tugaibei, N.L. Bereznykova, V.N. Karvechenko and A.V. Turov, Chem. Heterocycl. Comp., 5, 718 (2008); https://doi.org/10.1007/s10593-008-0076-7.
  13. M. Kurono, M. Hayashi, K. Miura, Y. Isogawa and K. Sawai, Japanese Kokai Tokkyo Koho, 62-267, 272 (1987); Chem. Abstr., 109, 37832 (1988).
  14. S.Q. Wang, L. Fang, X.J. Liu and K. Zhao, Chin. Chem. Lett., 15, 885 (2004).
  15. W. Yang, Z. Ruan, Y. Wang, K. Van Kirk, Z. Ma, B.J. Arey, C.B. Cooper, R. Seethala, J.H.M. Feyen and J.K. Dickson, J. Med. Chem., 52, 1204 (2009); https://doi.org/10.1021/jm801178c.
  16. R.J. Gillespie, S.J. Bamford, R. Botting, M. Comer, S. Denny, S. Gaur, M. Griffin, A.M. Jordan, A.R. Knight, J. Lerpiniere, S. Leonardi, S. Lightowler, S. McAteer, A. Merrett, A. Misra, A. Padfield, M. Reece, M. Saadi, D.L. Selwood, G.C. Stratton, D. Surry, R. Todd, X. Tong, V. Ruston, R. Upton and S.M. Weiss, J. Med. Chem., 52, 33 (2009); https://doi.org/10.1021/jm800961g.
  17. O. Stanisaw, Jordan J. Chem., 4, 1 (2009).
  18. B. Padamshari, V.P. Vaidya and M.L. Vijayayakumar, Indian J. Heterocycl. Chem., 12, 89 (2002).
  19. G.L. Ellman, K.P. Courtney, V. Andres Jr. and R.M.F. Stone, Biochem. Pharmacol., 7, 88 (1961); https://doi.org/10.1016/0006-2952(61)90145-9.
  20. N. Zaizafoon, Int. J. Biochem. Res. Rev., 7, 100 (2015); https://doi.org/10.9734/IJBCRR/2015/15784.
  21. S. Tu, H. Jiang, F. Fang, Y. Feng, S. Zhu, T. Li, X. Zhang and D. Shi, J. Chem. Res., 396 (2004); https://doi.org/10.3184/0308234041423781.
  22. R. Medyouni, N. Hamdi, R.B. Said, A.S. Al-Ayed and F. Zagrouba1, J. Chem., Article ID 47265 (2012); https://doi.org/10.1155/2013/472657.
  23. M.X.W. Jiang, N.C. Warshakoon and M.J. Miller, J. Org. Chem., 70, 2824 (2005); https://doi.org/10.1021/jo0484070.
  24. J.A. Markwalder, M.R. Arnone, P.A. Benfield, M. Boisclair, G.R. Burton, C.H. Chang, S.S. Cox, P.M. Czerniak, C.L. Dean, D. Doleniak, R. Grafstrom, B.A. Harrison, R.F. Kaltenbach, D.A. Nugiel, K.A. Rossi, S.R. Sherk, L.M. Sisk, P. Stouten, G.L. Trainor, P. Worland and S.P. Seitz, J. Med. Chem., 47, 5894 (2004); https://doi.org/10.1021/jm020455u.
  25. S. Schenone, O. Bruno, M. Radi and M. Botta, Mini Rev. Org. Chem., 6, 220 (2009); https://doi.org/10.2174/157019309788922739.
  26. R.K. Hemender, R.A. Panduranga, V. Veeranagaiah and N. Versatile, Indian J. Chem., 31B, 163 (1992).
  27. X. Zhang, Q. Lin and P. Zhong, Molecules, 15, 3079 (2010); https://doi.org/10.3390/molecules15053079.
  28. N.A. Al-Masoudi, H.H. Mohammed, A.M. Hamdy, O.A. Akrawi, N. Eleya, A. Spannenberg, C. Pannecouque and P. Langer, Z. Naturforsch, 68b, 229 (2013).
  29. S.S. Brown, W. Kalow, W. Pilz, M. Whittaker and C.L. Woronic, Adv. Clin. Chem., 22, 1 (1981); https://doi.org/10.1016/S0065-2423(08)60046-3.
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