9th International Science Congress (ISC-2019).  International E-publication: Publish Projects, Dissertation, Theses, Books, Souvenir, Conference Proceeding with ISBN.  International E-Bulletin: Information/News regarding: Academics and Research

Design, Synthesis, Characterization and Biological Evaluation of Various N-substituted Piperazine Annulated s-Triazine Derivatives

Author Affiliations

  • 1Department of Chemistry, Sir P. T. Sarvajanik College of Science, Athwalines, Surat-395007, Gujarat, INDIA

Res.J.chem.sci., Volume 4, Issue (5), Pages 14-19, May,18 (2014)

Abstract

In an effort to discover new candidate, ten compounds were synthesized in a series of 2,4,6-trichloro-1,3,5-s-triazine analogues which in substitution with anisole, 4-hydroxy coumarin and different N-substituted piperazine derivatives on the C-6 position of s-triazine ring. The title compounds were screened for their in vitro antimicrobial activity against two gram-negative bacteria (E. coli, K. pneumoniae), two gram-positive bacteria (S. aureus, B. subtilis) and two fungal species (C. albicans and S. cerevisiae) using the disc diffusion method. Most of the synthesized compounds appeared with promising antimicrobial activity. The structure of the novel compounds were elucidated on the basis of IR, H NMR and elemental analysis.

References

  1. Srinivas K., Srinivas U., Bhanuprakash K., Harakishore K., Murty U. S. N. and Rao V. J., Synthesis and antibacterial activity of various substituted s-triazines, Eur. J. Med. Chem., 41, 1240-1246 (2006)
  2. Patel R.V., Kumari P., Rajani D.P. and Chikhalia K.H., Synthesis and studies of novel 2-(4- cyano-3-trifluoromethylphenyl amino)-4(quinolin-4-yloxy)-6-(piperazinyl/piperidinyl)-s-triazines as potential antimicrobial, antimycobacterial and anticancer agents, Eur. J. Med. Chem.,46, 4354-4365 (2011)
  3. Modh R. P., Patel A. C. and Chikhalia K. H., Design, synthesis, antibacterial, and antifungal studies of novel 3-substituted coumarinyl-triazine derivatives, Heterocycl. Commun.,19, 343-349 (2013)
  4. Indorkar D., Chourasia O.P. and Limaye S.N., Preparation of 2-substituted phenyl-3-bis-2,4-(methylphenyl, 4-amino)-s-triazine-6-ylaminobenzoylamino-5-H-4-thiazolidinone computational studies of PC model, Res.J. Chem. Sci.,3(10), 24-30 (2013)
  5. Menicagli R., Samaritani S., Signore G., Vaglini F. and Via L., In vitro cytotoxic activities of 2-alkyl-4,6-diheteroalkyl-1,3,5-triazines: New molecules in anticancer research, J. Med. Chem.,47, 4649- 4652 (2004)
  6. Melato S., Prosperi D., Coghi P., Basillico N. and Monti D., A Combinatorial approach to 2,4,6-trisubstituted triazines with potent antimalarial activity: Combining conventional synthesis and microwave assistance, ChemMedChem.,, 873-876 (2008)
  7. Desai S.D., Desai K.R., Chikhalia K.H., Clercq E.D. and Pannecouque C., Synthesis of a novel class of some 1,3,5-triazine derivatives and their anti-HIV activity, Int. J. drug design and Discov.,, 361-368 (2011)
  8. Mahajan D.H., Chikhalia K.H., Pannacoueque C. and Clercq E.D., Synthesis and studies of new 2-(coumarin-4-yl-oxy)-4,6-(substituted)-s-triazine derivatives as potential anti-HIV agents, Arch. Pharm. Chem. Life Sci.,342, 281-290 (2009)
  9. Chen X., Zhan P., Liu X., Clercq E.D., Pannecouque C. and Balzarini J., Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors, Eur. J. Med. Chem., 51, 60-66 (2012)
  10. Dao P., Jarray R., Coq J. L., Lietha D., Loukaci A., Garbay C., Raynaud F. and Chen H., Synthesis of novel diarylamino-1,3,5-triazine derivatives as FAK inhibitors with anti-angiogenic activity, Bioorg. & Med. Chem. Lett., 23, 4552-4556 (2013)
  11. Mari S., Rossi M., Valenti P. and Da Re P., Flavone and xanthone derivatives related to fluoroquinolones, IL Farmaco,54, 411-415 (1999)
  12. Wyrzykiewicz E.,Wendzonka M. and KedziB.,Synthesis andantimicrobial activity of new (E)-4-[piperidino(4-methylpiperidino-, morpholino-)N-alkoxy]stillbenes, Eur. J. Med. Chem., 41, 519-525 (2006)
  13. Singh K.K., Joshi S.C. and Mathela C.S., Synthesis and invitro antibacterial activity of N-aryl piperazine derivatives, Ind. J. Chem.,50B, 196-200 (2011)
  14. Anandakumar C.S., Vinaya K., Sharathchandra J.N., Thimmegowda N.R., Benkaprasad S.B., Sadashiva C.T. and Rangappa K.S., Synthesis and antimicrobial studies of novel 1-benzhydryl-piperazine sulfonamide and carboxamide derivatives, J. Enz. Inhibition & Med. Chem.,23, 462-469 (2008)
  15. Dinsmore C.J. and Beshore D.C., Recent advances in the synthesis of diketopiperazines, Tetrahedron,58, 3297-3312 (2002)
  16. Todorovic A. and Haskell-Luevano C., A review of melanocortin receptor small molecule ligands. Peptides,26, 2026-2036 (2005)
  17. Kerns R.J., Rybak M.J., Kaatz G.W., Vaka F., Cha R., Grucz R.G. and Diwadkar V.U., Structural features of piperazinyl-linked ciprofloxacin dimmers required for activity against drug-resistance strains of staphylococcus aureus, Bioorg. Med. Chem. Lett.,13, 2109-2112 (2003)
  18. Ryckebusch A., Poulain R., Maes L., Debreu-Fontaine M. A., Mouray E., Grellier P. and Sergheraert C., Synthesis and in vitro and in vivo antimalarial activity of N-(7-chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine derivatives, J. Med. Chem.,46, 542-557 (2003)
  19. Kimura M., Masuda T., Yamadaa K., Mitania M., Kubota N., Kawakatsu N., Kishii K., Inazu M., Kiuchi Y., Oguchi K.and Namiki T.,Novel diphenylalkyl piperazine derivatives with high affinities for the dopamine transporter, Bioorg. & Med. Chem., 11, 3953-3963 (2003)
  20. Bruckner H. and Strecker B., Use of chiral monohalo-s-triazine reagents for the liquid chromatographic resolution of DL-amino acids, J. Chromatogr., 627, 97-105 (1992)
  21. Bauer A. W., Kirby W. M. M., Sherris J. C. and Turck M., Antibiotic susceptibility testing by a standardize single disc method, Am. J. clin. Path.,45, 493-496 (1966)
  22. Performance standards for antimicrobial disc susceptibility tests; approved standard M2-A6, National Committee for Clinical Laboratory Standards (NCCLS) Wayne, Pa (1997)