DOI QR코드

DOI QR Code

Design, Synthesis and Antibacterial Activity Studies of Novel Quinoline Carboxamide Derivatives

  • Shivaraj, Yellappa ;
  • Naveen, Malenahalli H. ;
  • Vijayakumar, Giriyapura R. ;
  • Kumar, Doyijode B. Aruna
  • Received : 2012.11.27
  • Accepted : 2013.03.13
  • Published : 2013.04.20

Abstract

A series of novel quinoline-6-carboxamides and 2-chloroquinoline-4-carboxamides were synthesized by the reaction of their analogous carboxylic acids with various amine derivatives in the presence of base TEA and protecting agent BOP at room temperature. Synthesized compounds were confirmed by spectral characterization viz IR, $^1H$-NMR, and MS. Antibacterial activity carried out against Escherichia coli and Staphyllococcus aureus indicated that the synthesized compounds were active against these microorganisms.

Keywords

Quinoline-6-carboxamides;2-Chloro quinoline-4-carboxamides;Antibacterial activity

References

  1. Roma, G.; Grossi, G.; Di Braccio, M.; Piras, D.; Ballabeni, V.; Tognolini, M.; Bertoni, S.; Barocelli. E. Eur. J. Med. Chem. 2008, 43, 1665. https://doi.org/10.1016/j.ejmech.2007.10.010
  2. Venkat Reddy, G.; et al. Eur. J. Med. Chem. 2009, 44, 1570. https://doi.org/10.1016/j.ejmech.2008.07.024
  3. Tomassoli, I.; et al. Eur. J. Med. Chem. 2011, 46, 1. https://doi.org/10.1016/j.ejmech.2010.08.054
  4. Sliman, F.; Blairvacq, M.; Durieu, E.; Meijer, L.; Rodrigo, J.; Desmaele, D. Bioorg. Med. Chem. Lett. 2010, 20, 2801. https://doi.org/10.1016/j.bmcl.2010.03.061
  5. Zhang, J.; Ke, X.; Tu, C.; Lin, J.; Ding, J.; Lin, L.; Fun, H. K.; You, X.; Guo, Z. Biometals. 2003, 16, 485. https://doi.org/10.1023/A:1022577420708
  6. Tsuji, K.; Spears, G. W.; Nakamura, K.; Tojo, T.; Seki, N.; Sugiyama, A.; Matsuo, M. Bioorg. Med. Chem. Lett. 2002, 12, 85. https://doi.org/10.1016/S0960-894X(01)00671-0
  7. Bu, X.; Chen, J.; Deady, L. W.; Smith, C. L.; Baguley, B. C.; Greenhalgh, D.; Yang, S.; Denny, W. A. Bioorg. Med. Chem. Lett. 2005, 13, 3657. https://doi.org/10.1016/j.bmc.2005.03.033
  8. Liu, J.-Y.; Yu, H.-L.; Quan, Z.-S.; Cui, X.; Piao, H.-R. Bioorg. Med. Chem. Lett. 2009, 19, 2392. https://doi.org/10.1016/j.bmcl.2009.03.089
  9. Belloli, S.; et al. Neurochem. International, 2004, 44, 433. https://doi.org/10.1016/j.neuint.2003.08.006
  10. Wentland, M. P.; et al. Drug Des Discov. 1997, 15, 25.
  11. Pelczar, M. J.; Chan, E. C. S. Laboratory Exercise in Microbiology; McGraw-Hill Inc: USA, 1997, Vo. 17, p 301.
  12. Cruickshank, R.; Duguid, J. P.; Marmion, B. P.; Swain, R. H. A. Med. Microbiol. 1989, 201.
  13. EUCAST Definitive Document. Determination of Minimum Inhibitory Concentrations (MICs) of Antimicrobial Agents by Agar Dilution. 2000, Vol. 6, pp 509−515.

Cited by

  1. ACCERBATIN, a small molecule at the intersection of auxin and reactive oxygen species homeostasis with herbicidal properties vol.68, pp.15, 2017, https://doi.org/10.1093/jxb/erx242
  2. 15-(4-Chlorophenyl)-6b-hydroxy-17-methyl-6b,7,16,17-tetrahydro-7,14a-methanonaphtho[1′,8′:1,2,3]pyrrolo[3′,2′:8,8a]azuleno[5,6-b]quinolin-14(15H)-one methanol hemisolvate vol.1, pp.4, 2016, https://doi.org/10.1107/S2414314616006374
  3. Green chemical approach: microwave assisted, titanium dioxide nanoparticles catalyzed, convenient and efficient C–C bond formation in the synthesis of highly functionalized quinolines and quinolinones vol.4, pp.84, 2014, https://doi.org/10.1039/C4RA06772J
  4. Synthesis, structure, spectroscopic investigations, and computational studies of optically pure β-ketoamide vol.61, pp.7, 2016, https://doi.org/10.1134/S1063774516070075
  5. Physicochemical and Critical Micelle Concentration (CMC) of Cationic (CATB) and Anionic (SDS) Surfactants with Environmentally Benign Blue Emitting TTQC Dye vol.25, pp.6, 2015, https://doi.org/10.1007/s10895-015-1621-2
  6. Synthesis and Bioactivity of Quinoline-3-carboxamide Derivatives vol.55, pp.4, 2018, https://doi.org/10.1002/jhet.3132