DOI QR코드

DOI QR Code

A Green Chemical Approach towards the 'One-Pot' Synthesis, Spectral Characterization and in Vitro Antibacterial and Antifungal Activities of Morpholino Pyrimidines

친환경적 One Pot 합성, In Vitro에서 Morpholino Pyrimidines의 분광학적 특성과 항균성 및 항진균성

  • Kanagarajan, V. (Synthetic Organic Chemistry Laboratory, Department of Chemistry, Annamalai University) ;
  • Thanusu, J. (Synthetic Organic Chemistry Laboratory, Department of Chemistry, Annamalai University) ;
  • Gopalakrishnan, M. (Synthetic Organic Chemistry Laboratory, Department of Chemistry, Annamalai University)
  • Published : 2009.12.20

Abstract

‘One-pot’ reaction procedure for the synthesis of novel morpholino pyrimidines (10-18) under microwave irradiation in ‘dry media’ in the presence of heterogeneous $NaHSO_4.SiO_2$ catalyst was developed. All the synthesized compounds were screened for their in vitro antibacterial activities against clinically isolated bacterial strains namely Bacillus subtilis, Bacillus cerues, Micrococcus luteus and Salmonella typhii and antifungal activities against fungal strains namely Aspergillus niger, Candida 6 and Candida 51. Structure activity relationship of the synthesized compounds against microbiological results was discussed.

$NaHSO_4.SiO_2$ 촉매를 이용한 microwave 및 무수조건하에서 새로운 morpholino pyrimidines의 One-pot합성이다. 합성된 모든 화합물을 이용하여 in vitro에서 임상학적인 단리된 박테리아 품종 즉 Bacillus subtilis, Bacillus cerues, Micrococcus luteus , Salmonella typhii에 대해 항균성을 살펴보았고, 균품종 즉 Aspergillus niger, Candida 6, Candida 51에 대해 항진균성을 살펴보았다. 미생물 결과에 대한 합성된 화합물의 구조적 활동성의 관련성에 대해 토론하였다.

Keywords

References

  1. Ramalingan, C.; Balasubramanian, S.; Kabilan, S.; Vasudevan, M. Eur. J. Med. Chem. 2004, 39, 527 https://doi.org/10.1016/j.ejmech.2004.02.005
  2. Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250 https://doi.org/10.1002/anie.200400655
  3. Lidstrom, P.; Tierney, J. P.; Wathey, B.; Westman, J. Microwave-Assisted Organic Synthesis, Ed.; Blackwell: Oxford, U. K. 2005
  4. Loupy, A. Microwaves in Organic Synthesis, Ed.; Wiley-VCH: Weinheim, 2006
  5. Leadbeater, N. E.; Schmink, J. R. Tetrahedron, 2007, 63, 6764 https://doi.org/10.1016/j.tet.2007.04.074
  6. Mercer, F. L.; Lindhorst, T. E.; Commoner, B. Science, 1953, 117, 558 https://doi.org/10.1126/science.117.3047.558
  7. Matolesy, G. World Rev. Pest. Contr. 1971, 10, 50
  8. Weishaar, R. E.; Cain, M. C.; Bristor, J. A. J. Med. Chem. 1999, 42, 805 https://doi.org/10.1021/jm980222w
  9. Commoner, B.; Mercer, F. L. Nature, 1951, 168, 113 https://doi.org/10.1038/168113a0
  10. Ram, V. J.; Singha, V. K.; Guru, P. Eur. J. Med. Chem. 1990, 25, 549 https://doi.org/10.1016/0223-5234(90)90179-7
  11. Ahluwalia, V. K.; Chauhan, A.; Khurana, A. Indian J. Chem. 1989, 28B, 964
  12. Tam, S. W.; Wong, Y. N.; Huang, S.; Shen, H. Eur. J. Med. Chem. 1999, 42, 809
  13. Goyal, R. N. Bhusan, R.; Agarwal, A. J. Indian Chem. Soc. 1985, 62, 229
  14. Hamilton, D. J; Sutherland, A. Tetrahedron Lett. 2004, 45, 5739 https://doi.org/10.1016/j.tetlet.2004.05.096
  15. Akyuz, S.; Akyuz, T. J. Mol. Struct. 2005, 744, 881 https://doi.org/10.1016/j.molstruc.2004.11.077
  16. Akyuz, S. J. Mol. Struct. 2003, 651, 205 https://doi.org/10.1016/S0022-2860(02)00659-2
  17. Manfred, R.; Michael, M.; Robert, S.; Wolfgang, G. Eur. Pat. Appl. EP 1989, 28, 334146. Chem. Abstr. 1989, 112, 178999
  18. Manfred, R.; Michael, M.; Robert, S.; Wolfgang, G.; Eckhard, R. Ger. Offen. DE 1989, 17, 3729285. Chem. Abstr. 1989, 111, 134172
  19. Hale, J. J.; Mills, S. G.; MacCross, M.; Dorn, C. P.; Fink, P. E.; Budhu, R. J.; Reamer, R. A.; Huskey, W. P.; Luffer-Atlas, D.; Dean, B. J.; McGowan, E. M.; Feeney, W. P.; Chiu, S. H. L.; Cascieri, M. A.; Chicchi, G. G.; Kurtz, M. M.; Sadowski, S.; Ber, E.; Tattersall, F. D.; Rupniak, N. M. J.; Williams, A. R.; Raycroft, W.; Hargreaves, R.; Metzger, J. M.; Maclntyre, D. E. J. Med. Chem. 2000, 43, 1234 https://doi.org/10.1021/jm990617v
  20. Dorn, C. P.; Hale, J. J. MacCoss, M.; Mills, S. G. U. S. Patent 1997, 82, 5691336. Chem. Abstr. 1997, 128, 48231
  21. Fisher, M. H.; Wyvratt, M. J. U. S. Patent 1991, 10, 5077290. Chem. Abstr. 1991, 116, 214513
  22. Avramova, P.; Danchev, N.; Buyukliev, R.; Bogoslovova, T.; Arch. Pharm. 1998, 331, 342 https://doi.org/10.1002/(SICI)1521-4184(199811)331:11<342::AID-ARDP342>3.0.CO;2-6
  23. Tietze, L. F.; Nils Rackelmann. Pure Appl. Chem. 2004, 76, 1967 https://doi.org/10.1351/pac200476111967
  24. Gopalakrishnan, M.; Sureshkumar, P.; Thanusu, J.; Prabhu, C.; Kanagarajan, V. J. Chem. Res. 2007, 2, 80 https://doi.org/10.1021/ar50015a003
  25. Gopalakrishnan, M.; Sureshkumar, P.; Kanagarajan, V.; Thanusu, J.; Govindaraju, R. J. Chem. Res. 2005, 5, 299
  26. Gopalakrishnan, M.; Thanusu, J.; Kanagarajan, V. J. of Korean Chem. Soc. 2008, 52, 47 https://doi.org/10.5012/jkcs.2008.52.1.047
  27. Gopalakrishnan, M.; Kanagarajan, V.; Thanusu, J. Green Chem. Lett. 2008, 1, 241 https://doi.org/10.1080/17518250802644617
  28. Gopalakrishnan, M.; Sureshkumar, P.; Kanagarajan, V.; Thanusu, J. J. Korean Chem. Soc. 2007, 51, 346 https://doi.org/10.5012/jkcs.2007.51.4.346
  29. Kothari, S.; Singhal, M.; Vijayvergia, D.; Vyas, R.; Verma, B.L. J. Indian Chem. Soc. 2000, 77, 29
  30. Dhar, M. H.; Dhar, M. M.; Dhawan, B. N.; Mehrotra, B. N.; Ray, C.; Indian J. Exp. Biol. 1968, 6, 232

Cited by

  1. Reaction of polyfluorinated chalcones with guanidine vol.51, pp.12, 2015, https://doi.org/10.1134/S1070428015120143
  2. Environmentally benign synthesis of heterocyclic compounds by combined microwave-assisted heterogeneous catalytic approaches† vol.14, pp.1, 2012, https://doi.org/10.1039/C1GC15837F
  3. Novel Synthesis of bis Acetylated Hybrid Pyrazoles as Potent Anticandidiasis Agents vol.55, pp.2, 2011, https://doi.org/10.5012/jkcs.2011.55.2.256
  4. Review on the Synthesis of Six-MemberedN,N-Heterocycles by Microwave Irradiation vol.45, pp.10, 2015, https://doi.org/10.1080/00397911.2013.827208
  5. Significance and Biological Importance of Pyrimidine in the Microbial World vol.2014, 2014, https://doi.org/10.1155/2014/202784
  6. Synthesis of Novel 2-Amino-substituted 6-Methyl-pyrimidin-4-ol Derivatives and Their Biological Evaluation vol.16, pp.7, 2009, https://doi.org/10.2174/1570178615666181025120951
  7. Synthesis and Biological Activity of New 2-{[6-Methyl-2-(pyrrolidin-1-yl)pyrimidin-4-yl]oxy}acetohydrazide Derivatives vol.89, pp.10, 2009, https://doi.org/10.1134/s1070363219100050
  8. Synthesis and Plant Growth Stimulating Action of 2-Amino-6-methylpyrimidine-4(3H)-thione Derivatives vol.90, pp.2, 2009, https://doi.org/10.1134/s1070363220020073