Skip to main navigation menu Skip to main content Skip to site footer

Vol. 10 No. 1.0 (2021)
Scholar : National School of Leadership

Research Articles

SYNTHESES OF 4, 6-DIPHENYLPYRIMIDIN-2-ONE AND 4, 6 DIPHENYLPYRIMIDE-2-THIONE FROM BENZALACETOPHENONE (CHALCONE)

Published 2021-06-30

  • RATHEESH S. NAIR
    • ,
  • SUJU C JOSEPH

RATHEESH S. NAIR
MAR IVANIOS COLLEGE

SUJU C JOSEPH
MAR IVANIOS COLLEGE

Abstract

Nitrogen containing heterocyclic compounds dihydropyrimidinone and its sulphur analogue, diphenylpyrimidine-2-thione, have been reported to possess many pharmacological properties such as anticancer, anti-HIV, antibacterial, antimalarial, antihypertensive, sedative, hypnotics, anticonvulsant, antithyroid and as antibiotics. 4, 6- diphenylpyrimidin-2-one and 4, 6-diphenylpyramidine-2-thione were synthesised by the reaction of benzalacetophenone (chalcone) with urea and thiourea respectively using ethanol as the solvent. Benzalacetophenone was synthesized by Claisen-Schmidt reaction by condensing acetophenone with benzaldehyde in the presence of an aqueous alkali. The structures of benzalacetophenone (chalcone), 4, 6-diphenylpyrimidin-2-one and 4, 6-diphenylpyrimidine-2-thione were confirmed by NMR (1H, 13C), FTIR & MASS spectral data

References

  1. (a) Katritzky, A. R.;Pozharskii, A. F., Handbook of Heterocyclic Chemistry:2nd ed.; Pergamon Press: New York, 2000. (b) E. J. Noga,;Barthalmus. G. T;.Mitchell, M.K.; Cell Biology Int. Rep., 10, 239, 1986.
  2. (a) Mori,; A.;Sekiguchi, K.; Masui, M.;Horie, T.; Ikeda. L; Shimoda,T.J. Am.Chem. Soc., 125, 1700, 2003.
  3. Nagaraj. A.; Sanjeeva Reddy.; J. Iran. Chem. Soc., 5, 262, 2008.
  4. Mahadevan, K.M.;Prakash, G.K.;Anunakumar, D. B.;Kumaraswamy, B.;Sherigara, B.S.; Indian J. Chem., 45 B, 1699, 2006.
  5. Kostanecki. M.;Tambor, S.A.;ActaPharma, 58, 467, 1989.
  6. Atwal, K.S.;.Rovnyak, G.C.; J. Med. Chem.,33, 2629, 1990.
  7. Fabio, K. H.;Popat, K. H.;Vasoya. S. L. Indian J. HeterocyclicChem.,12, 217, 1992.
  8. Vashi, K.;Naik, K. B. Asian J. Chem., 17, 240, 2005.
  9. Bhatt, D. J.;Kamdar, G. C.; Parikh, A. R. J. Inst. Chemists (India), 56, 233, 1984.
  10. Lakhani. R.; Parikh, J. Inst. Chemists (India), 59, 230, 1987.
  11. Joshi. H. S.; Parikh, A. R. J. Inst. Chemists (India), 62, 22, 251, 1990.
  12. Desai, C. M.; Patel, D.; Joshi, H. D. J. Inst. Chemists (India), 76,94, 2004. [1]M.B. Hogale, N.P. Dhore, A.R. Shelar, P.K. Pawar, Orient. J. Chem., 1986, 2, 55-57.
  13. T. Vamakawa, H. Kagechika, E. Kawachi, Y. Hashimoto, K. Shudo, J. Med. Chem., 1990, 33, 1430-1437.
  14. V. K. Ahluwalia, L. Nayal, N. Kaila, S. Bala , A. K. Tahim, Indian J. Chem., 1987, 26B, 384-386.
  15. A.K. Bhatt, R.P. Bhamaria, M.R. Patel, R.A. Bellare, C.V. Deliwala, Indian J. Chem., 1972, 10, 694-698.
  16. S. Mukherjee, V. Kumar, A.K. Prasad, H.G. Raj, M.E. Brakhe, C.E. Olsen, S.C. Jain, V.P. Parmar, Bio-org Med.
  17. Chem., 2001, 9, 337-345.
  18. S.A. Indyah, H. Timmerman, M. Samhoedi, D. Sastronami, H. Sugiyanto, V.D. Goot, Eur. J. Med. Chem., 2000,
  19. , 449.
  20. M. Chen, S.B. Christensen, L. Zhai, M.H. Rasmussen, T.G. Theander, S. Frokjaer, B. Steffensen, J. Davidson, A.
  21. Kharazmi, J. Infect. Dis., 1997, 176, 1327-1333.
  22. S.F. Nielsen, S.B. Christensen, G. Cruciani, A. Kharazmi, T. Liljefors, J. Med. Chem., 1998, 41, 4819-4832.
  23. R.Y. Prasad, P. Kumar, R.P. Kumar, P.V. Rao, Int. J. Chem. Sci., 2008, 6(1), 333-341.
  24. V.P. Vaidya, P. Mathias, Ind. J. Het. Chem., 2005, 14, 189-192.
  25. New OECD 425 Guidelines. OECD Guidelines for testing of Animals (2001). Dec, 1-26.
  26. M.N. Ghosh, Experimental Pharmacology, Hilton and company, Kolkata, 2005.
  27. (1.) Ghorab M M, Heiba M I, Hassan A A, AbdEIAzizA B and El-Gazzar M G, Antimicrobial Journal of American science, 2011, 7(1), 1063-1072.
  28. (2.) SalehiP, Dabiri M, Khosropour A R and Roozbehniya P, Diammonium hydrogen phosphate
  29. , Journal of the Iranian Chemical Society, 2006, 3(1), 98-104.
  30. (3.) Singh O M, Devi N S, Devi L R, Khumanthem N-
  31. International Journal of Drug Design and Discovery, 2010, 1(3), 258-264.
  32. (4.) Hed L C, Sharma R, Pareek C and Chaudhari P B Journal of Chemistry, 2009, 6(3), 770-774.
  33. (5.) RussowskyD, Benvenutti E V, Roxo G S and Chem., 2007, 4, 39-42.
  34. (6.) Rameshwar N, Parthasarathy T and Ram Reddy A, Indian J. Chem., 2008, 47B, 1871-1875.
  35. (7.) Solankee A N, Patel G A, Patel R B, Patel B K P 2010, 2(4), 336-341.
  36. (8.) Shah T B, Gupte A, Patel M R, Chaudhari V S, Patel H and Patel V C, Indian J Chem, 2009, 48B, 88-96.
  37. (10 )Eajasekaran S, Rao G K, Sanjay Pai P N and Ajay A K, Journal of Pharm Tech Research, 2011, 3(2), 626-631.
  38. (11.)Gangadasu B,Narender P, Raju B C, Rao V J, , Indian J Chem, 2006, 15B, 1259-1263.
  39. (12.)Atwal K S, Swanson B N, Umger S E, Floyd D M, Moreland S, Hedberg A, Reilly B C,
  40. J. Med Chem, 1991,34,806.
  41. (13.)Hu E H, SidlerD R, Dolling U H, Unprecedented J Org Chem., 1998, 63, 3454.
  42. (14.)Patil A D, Kumar N V, Kokko W C, Bean M F, Freyer A J, Debrosse C etal, J Org Chem1995, 60, 1182.
  43. (15.)Snider B B, Chen J J, Patil A D, Freyer A,1996,37, 6977.
  44. (16.)Verma S and Aslam M, Oriental Journal of Chemistry,2011,27(3), (In press).