Synthesis, Characterization and Biological Activity Of 1, 4-Dihydropyrimido [1,2-A] Benzimidazole

Authors

  • Vaishnavi. P. Gilava  Department of Chemistry, Smt. J. A. Patel Mahila College, Morbi, Gujarat, India
  • Dr. Praful. K. Patel  Department of Chemistry, Smt. J. A. Patel Mahila College, Morbi, Gujarat, India

DOI:

https://doi.org/10.32628/IJSRSET218630

Keywords:

1,4-dihydropyrimido[1,2-a]benzimidazole, 1H-benzo[d]imidazol-2-amine, 4-(benzyloxy)-3-methoxybenzaldehyde, N-(substituted phenyl)-3-oxobutanamide, Antimicrobial activity.

Abstract

An effectual direct synthesis of 1,4-dihydropyrimido[1,2-a]benzimidazole (C-01 to C-10) was developed from 1H-benzo[d]imidazol-2-amine, 4-(benzyloxy)-3-methoxybenzaldehyde, N-(substituted phenyl)-3-oxobutanamide by adding few drop of DMF and in presence of conc.HCL. The product was obtained after about 5 hours of heating in refluxing condition. The synthesized compounds were characterized by different spectral and elemental analysis. Some of the obtained compounds showed a promising antimicrobial activity on screening against Gram-positive and Gram-negative bacterial strains.

References

  1. B. Beovi´c, Int. J. Food Microbiol., 2006, 112, 280–287.
  2. D. T. W. Chu, J. J. Plattner and L. Katz, J. Med. Chem., 1996,39, 3853–3874.
  3. R. Finch and P. A. Hunter, J. Antimicrob. Chemother., 2006, 58(Suppl 1), i3– i22.
  4. T. D. Gootz, Crit. Rev. Immunol., 2010, 30, 79–93.
  5. D. Niccolai, L. Tarsi and R. J. Thomas, Chem. Commun., 1997,2333–2342, DOI:  10.1039/a704497f.
  6. K. M. Overbye and J. F. Barrett, Drug Discovery Today, 2005,10, 45–52.
  7. N. Suree, M. E. Jung and R. T. Clubb, Mini-Rev. Med. Chem., 2007, 7, 991–   1000.
  8. A. Travis, O. Chernova, V. Chernov and R. Aminov, Expert Opin. Drug   Discovery, 2018, 13,  983–985.
  9. F. Gao, T. Wang, J. Xiao and G. Huang, Eur. J. Med. Chem., 2019, 173, 274–281.
  10. R.Soni, G. Singh, R. Kaur, G. Kaur, R.K.Gill, J.Bariwal, Chemistry & biology interface,  Chem.Biol.4(2014) 163-175
  11. Begunov, R. S.; Ryzvanovich, G. A. Russ. Chem. Rev. 2013, 82, 77. [Usp. Khim. 2013, 82, 77.]
  12. Achar, K. C. S.; Hosamani, K. M.; Seetharamareddy, H. R. Eur. J. Med. Chem. 2010, 45, 2048.
  13. Podunavac-Kuzmanović, S. O.; Cvetković, D. D. Chem. Ind. Chem. Eng. Q. 2011, 17,33.
  14. Andrzejewska, M.; Yépez-Mulia, L.; Cedillo-Rivera, R.; Tapia, A.; Vilpo, L.; Vilpo, J.; Kazimierczuk, Z. Eur. J. Med. Chem. 2002, 37, 973.
  15. LaBarbera, D. V.; Skibo, E. B. Bioorg. Med. Chem. 2005, 13, 387.
  16. Agh-Atabay, N.; Dulger, B.; Gucin, F. Eur. J. Med. Chem. 2003, 38, 875.
  17. Sharma, D.; Narasimhan, B.; Kumar, P.; Judge, V.; Narang, R.; De Clercq, E.; Balzarini, J. J. Enzyme Inhib. Med. Chem. 2009, 24, 1161.
  18. Sondhi, S. M.; Rani, R.; Singh, J.; Roy, P.; Agrawal, S. K.; Saxena, A. K. Bioorg. Med. Chem. Lett. 2010, 20, 2306.
  19. Ndakala, A. J.; Gessner, R. K.; Gitari, P. W.; October, N.; White, K. L.; Hudson, A.; Fakorede, F.; Shackleford, D. M.; Kaiser M.; Yeates, C.; Charman, S. A.; Chibale, K. J. Med. Chem. 2011, 54, 4581.
  20. Ansari, K. F.; Lal, C. Eur. J. Med. Chem. 2009, 44, 4028.
  21. Kerimov, I.; Ayhan-Kilcigil, G.; Can-Eke, B.; Altanlar, N.; İscan, M. J. Enzyme Inhib. Med. Chem. 2009, 22, 696.
  22. Pieroni, M.; Tipparaju, S. K.; Lun, S.; Song, Y.; Sturm, A. W.; Bishai, W. R.; Kozikowski, A. P. ChemMedChem 2011, 6, 334.
  23. Chou, S.; Marousek, G. I. Antimicrob. Agents Chemother. 2006, 50, 3470.
  24. Oukoloff, K.; Lucero, B.; Francisco, K. R.; Brunden, K. R.; Ballatore, C. Eur. J. Med. Chem. 2019, 165, 332.
  25. Savateev, K. V.; Fedotov, V. V.; Ulomsky, E. N.; Rusinov, V. L. Chem. Heterocycl. Compd. 2018, 54, 197. [Khim. Geterotsikl. Soedinen. 2018, 54, 197.]
  26. Savateev, K. V.; Ulomsky, E. N.; Fedotov, V. V.; Rusinov, V. L.; Sivak, K. V.; Lyubishin, M. M.; Kuzmich, N. N.; Aleksandrov, A. G. Russ. J. Bioorg. Chem. 2017, 43, 421. [Bioorgan. Khim. 2017, 43, 402.]
  27. Zhang, N.; Ayral-Kaloustian, S.; Nguyen, T.; Afragola, J.; Hernandez, R.; Lucas, J.; Gibbsons, J.; Beyer, C. J. Med. Chem. 2007, 50, 319.
  28. Savateev, K.; Fedotov, V.; Butorin, I.; Eltsov, O.; Slepukhin, P.; Ulomsky, E.; Rusinov, V.; Litvinov, R.; Babkov, D.; Khokhlacheva, E.; Radaev, P.; Vassiliev, P.; Spasov, A. Eur. J. Med. Chem. 2020, 185, 111808.

International Journal of Scientific Research in Science, Engineering and Technology

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Published

2021-12-30

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Volume 8, Issue 6, November-December-2021

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Research Articles

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[1]
Vaishnavi. P. Gilava, Dr. Praful. K. Patel "Synthesis, Characterization and Biological Activity Of 1, 4-Dihydropyrimido [1,2-A] Benzimidazole" International Journal of Scientific Research in Science, Engineering and Technology (IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099, Volume 8, Issue 6, pp.267-274, November-December-2021. Available at doi : https://doi.org/10.32628/IJSRSET218630