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Russian Journal of General Chemistry

, Volume 89, Issue 2, pp 339–347 | Cite as

Pyrazole and Nicotinonitrile Derivatives Synthesized from Sulfa Drugs, and Their Antibacterial Activity

  • H. A. El-SayedEmail author
  • A. H. Moustafa
  • A. A. Fadda
  • K. E. Abd El-Rahman
Article
  • 14 Downloads

Abstract

Utility of sulfadiazine and sulfaguanidine in synthesis of new series of pyrazoles and 2-pyridones is described. Diazotization of sulfadiazine that results in formation of diazonium salt 2 followed by coupling of the latter with active methylene compounds leads to hydrazinyl derivatives 3a–3d. Heterocyclization of compounds 3a–3c with hydrazine derivatives gives to a series of pyrazole derivatives 4–6. Similarly, a series of pyrazole derivatives 12–14 is developed from sulfaguanidine. Condensation of hydrazinyl derivatives 3a–3c with cyanoacetamide in the presence of a catalytic amount of piperidine gives 2-oxonicotinonitriles 15a–15c. Tests of the new synthesized compounds against four pathogenic gram (+ve) and gram (−ve) bacteria demonstrate their activity higher than that of the standard Amoxicillin.

Keywords

sulfa-drugs pyrazole derivatives 2-pyridone derivatives diazonium salts antimicrobial activity 

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References

  1. 1.
    Iqbal, H., Prabhakar, V., Sangith, A., Chandrika, B., and Balasubramanian R., Med. Chem. Res., 2014, vol. 23, p. 4383. doi 10.1007/s00044-014-1007-zCrossRefGoogle Scholar
  2. 2.
    Bharatham, K., Bharatham, N., Park, K.H., and Lee, K.W., J. Mol. Graph. Modell., 2008, vol. 26, no. 8, p. 1202. doi 10.1016/j.jmgm.2007.11.002CrossRefGoogle Scholar
  3. 3.
    Gadad, A.K., Mahajanshetti, C.S., Nimbalkar, S., and Raichurkar, A., Eur. J. Med. Chem., 2000, vol. 35, no. 9, p. 853. doi 10.1016/S0223-5234(00)00166-5CrossRefGoogle Scholar
  4. 4.
    El-Sayed, H.A., Moustafa, A.H., El-Torky, A.E., Abd El-Salam E.A., Russ. J. Gen. Chem., 2017, vol. 87, no. 10, p. 2401. doi 10.1134/S107036321710022XCrossRefGoogle Scholar
  5. 5.
    Dominguez, J.N., Leon, C., Rodrigues, J., Dominguea, N.G.D., Gut, J., and Rosenthal, P.J., II Famaco, 2005, vol. 60, no. 4, p. 307. doi 10.1016/j.farmac.2005.01.005Google Scholar
  6. 6.
    Kim, T.-H., Seo, W.D., Ryu, H.W., Seo, H.R., Jin, Y.B., Lee, M., Ji, Y.-H., Park, K.H., and Lee, Y.-S., Chem. Biol. Interact., 2010, vol. 188, no. 1, p. 111. doi 10.1016/j.cbi.2010.06.016CrossRefGoogle Scholar
  7. 7.
    El-Sayed, H.A., Mostafa, A.H., Haikal, A.F.Z., Abu-El-Halwa, R., and El-Ashry, E.S.H., Eur. J. Med. Chem., 2011, vol. 46, no. 7, p. 2948. doi 10.1016/j.ejmech.2011.04.019CrossRefGoogle Scholar
  8. 8.
    Moustafa, A.H., El-Sayed, H.A., Haikal, A.Z., and Abd El-Hady, R.A., Nucleos. Nucleot. Nucleic Acid, 2013, vol. 32, no. 5 p. 221. doi 10.1080/15257770.2013.775449Google Scholar
  9. 9.
    Haggam, R.A., El-Sayed, H.A., Said, S.A., Ahmed, M.H.M., Moustafa, A.H., and Abd-El-Noor, R.E., J. Heterocycl. Chem., 2017, vol. 54, no. 1, p. 375. doi 10.1002/jhet.2593CrossRefGoogle Scholar
  10. 10.
    Ibrahim, T.S., El-Sayed, H.A., Khayat, M.T., Al-Mahmoudy, A.M.M., Moustafa, A.H., Saad El-Deen, A.K., Rostom, S.A.F., and Panda, S.S., Med. Chem., 2018, vol. 14, no. 8, p. 791. doi 10.2174/1573406414666180522123524CrossRefGoogle Scholar
  11. 11.
    El-Sayed, H.A., Said, S.A., Amr, A.E., and Abdalla, M.M., J. Comput. Theor. Nanosci. 2017, vol. 14, no. 11, p. 5315. doi 10.1166/jctn.2017.6941Google Scholar
  12. 12.
    Mahmood, Z., Ahmed, I., Mohammed, F., and Ahmed, S., Pharmaceut. Biol., 1999, vol. 37, no. 3, p. 237. doi 10.1076/phbi.37.3.237.6296CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • H. A. El-Sayed
    • 1
    Email author
  • A. H. Moustafa
    • 1
  • A. A. Fadda
    • 2
  • K. E. Abd El-Rahman
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceZagazig UniversityZagazigEgypt
  2. 2.Department of Chemistry, Faculty of ScienceMansoura UniversityMansouraEgypt

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