Skip to main content
SpringerLink
Log in

Design and synthesis of new (bis)trifluoromethyl-promoted N-aryl biquinoline derivatives as antitubercular and antimicrobial agents

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

A series of 2-((4-fluorophenyl)thio)quinoline linked (bis)-trifluoromethyl substituted N-arylquinolone derivatives 8a–x have been synthesized via a one-pot multicomponent reaction. The newly synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR, mass spectroscopy and elemental analysis. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains by Broth microdilution method and in vitro antituberculosis activity was evaluated against Mycobacterium tuberculosis H37Rv bacteria by Lowenstein–Jensen method.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Scheme 1
Scheme 2

Similar content being viewed by others

References

  • Alfredson TV, Maki AH, Waring M (1991) Optically detected triplet-state magnetic resonance studies of the DNA complexes of the bisquinoline analogue of echinomycin. Biochemistry 30:9665–9675

    Article  CAS  PubMed  Google Scholar 

  • Amit N, Vikramdeep M, Alpeshkumar M, Rahul E (2007) Synthesis, anti-tuberculosis activity, and 3D-QSAR study of 4-(adamantan-1-yl)-2-substituted quinolines. Bioorg Med Chem 15:626–640

    Article  Google Scholar 

  • Annamaria L, Jialin M, Baojie W, Yuehong W, Scott GF, Alan PK (2009) Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis. J Med Chem 52:2109–2118

    Article  Google Scholar 

  • Bloch AB, Cauthen GM, Onorato IM, Kenneth G, Dandbury G, Kelly GD, Driver CR, Snider DE (1994) Nationwide survey of drug-resistant tuberculosis in the United States. J Am Med Assoc 271:665–671

    Article  CAS  Google Scholar 

  • Centers for Disease Control Prevention (2006) Emergence of Mycobacterium tuberculosis with extensive resistance to second-line drugs worldwide, 2000 2004. MMWR Recomm Rep 55:301–305

    Google Scholar 

  • Chai Y, Wan ZL, Wang B, Guo HY, Liu ML (2009) Synthesis and in vitro antibacterial activity of 7-(4-alkoxyimino-3-amino-3-methylpiperidin-1-yl)fluoroquinolone derivatives. Eur J Med Chem 44:4063–4069

    Article  CAS  PubMed  Google Scholar 

  • Guillon J, Moreau S, Mouray E, Sinou V, Forfar I, Fabre SB, Desplat V, Millet P, Parzy D, Jarry C, Grellier P (2008) New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: synthesis, and in vitro antimalarial activity. Bioorg Med Chem 16:9133–9144

    Article  CAS  PubMed  Google Scholar 

  • Hagmann WK (2008) The many roles for fluorine in medicinal chemistry. J Med Chem 51:4359–4369

    Article  CAS  PubMed  Google Scholar 

  • Jardosh HH, Patel MP (2013) Design and synthesis of biquinolone–isoniazid hybrids as a new class of antitubercular and antimicrobial agents. Eur J Med Chem 65:348–359

    Article  CAS  PubMed  Google Scholar 

  • Kanani MB, Patel MP (2013) Synthesis and in vitro antimicrobial evaluation of novel 2-amino-6-(phenylthio)-4-(2-(phenylthio)quinolin-3-yl)pyridine-3,5-dicarbonitriles. Med Chem Res 22:2912–2920

    Article  CAS  Google Scholar 

  • Kathrotiya HG, Patel MP (2013) Synthesis and identification of β-aryloxyquinoline based diversely fluorine substituted N-aryl quinolone derivatives as a new class of antimicrobial, antituberculosis and antioxidant agents. Eur J Med Chem 63:675–684

    Article  CAS  PubMed  Google Scholar 

  • Kaur K, Jain M, Khan SI, Jacob MR, Tekwani BR, Singh S, Singh PP, Jaina R (2011) Synthesis, antiprotozoal, antimicrobial, β-hematin inhibition, cytotoxicity and methemoglobin (MetHb) formation activities of bis(8-aminoquinolines). Bioorg Med Chem 19:197–201

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Larghi EL, Bohn ML, Kaufman TS (2009) Aaptamine and related products. Their isolation, chemical syntheses, and biological activity. Tetrahedron 65:4257–4282

    Article  CAS  Google Scholar 

  • Meth-Cohn O, Bramha NA (1978) A versatile new synthesis of quinolines, thionopyridine and related fused pyridines. Tetrahedron Lett 23:2045–2048

  • Mital A, Negi AS, Ramachandran U (2006) Synthesis and antimycobacterial activities of certain trifluoromethyl-aminoquinoline derivatives. ARKIVOC 10:220–227

    Article  Google Scholar 

  • Muller K, Faeh C, Diederich F (2007) Fluorine in pharmaceuticals: looking beyond intuition. Science 317:1881–1886

    Article  PubMed  Google Scholar 

  • NCCLS (National Committee for Clinical Laboratory Standards) 2002 Performance standards for antimicrobial susceptibility testing: Twelfth informational supplement. ISBN 1-56238-454-6, M100-S12 (M7).

  • Palit P, Paira P, Hazra A, Banerjee S, Gupta AD, Dastidar SG, Mondal NB (2009) Phase transfer catalyzed synthesis of bis-quinolines: antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial. Eur J Med Chem 44:845–853

    Article  CAS  PubMed  Google Scholar 

  • Purser S, Moore PR, Swallow S, Gouverneur V (2008) Fluorine in medicinal chemistry. Chem Soc Rev 37:320–330

    Article  CAS  PubMed  Google Scholar 

  • Rastogi N, Kochi A, Vareldzis B, Styblo K, Crawford JT, Jarvis WR, McGowan JE, Perrone CJ, David HL, Zhang Y, Cohn DL, Iseman MD (1993a) Emergence of multiple-drug-resistance tuberculosis: fundamental and applied research aspects, global issues and current strategies. Res Microbiol 144:103–158

    Article  CAS  PubMed  Google Scholar 

  • Rastogi N, Ross BC, Dwyer B, Goh KS, Clavel-Seres S, Jeantils V, Cruaud P (1993b) Emergence during unsuccessful chemotherapy of multiple drug resistance in a strain of Mycobacterium tuberculosis. Eur J Clin Microbiol Infect Dis 11:901–907

    Article  Google Scholar 

  • Rattan A (2000) Antimicrobials in laboratory medicine. B.I. Churchill Livingstone, New Delhi, pp 85–108

    Google Scholar 

  • Raviglione MC, Smith I (2007) XDR tuberculosis—implications for global public health. N Engl J Med 356:656–659

    Article  CAS  PubMed  Google Scholar 

  • Raynes K, Galatis D, Cowman AF, Tilley L, Deady LW (1995) Synthesis and activity of some antimalarial bisquinolines. J Med Chem 38:204–206

    Article  CAS  PubMed  Google Scholar 

  • Shah NM, Patel MP, Patel RG (2012) New N-arylamino biquinoline derivatives: synthesis, antimicrobial, antituberculosis, and antimalarial evaluation. Eur J Med Chem 54:239–247

    Article  CAS  PubMed  Google Scholar 

  • Strekowski L, Say M, Zegrocka O, Tanious FA, Wilson WD, Manzel L, Macfarlane DE (2003) Bis-4-aminoquinolines: novel triple-helix DNA intercalators and antagonists of immunostimulatory CpG-oligodeoxynucleotides. Bioorg Med Chem 11:1079–1085

    Article  CAS  PubMed  Google Scholar 

  • Tewari S, Chauhan PMS, Bhaduri AP, Fatima N, Chatterjee RK (2000) Syntheses and antifilarial profile of 7-chloro-4-(substituted amino) quinolines: a new class of antifilarial agents. Bioorg Med Chem Lett 10:1409–1412

    Article  CAS  PubMed  Google Scholar 

  • Vennerstrom JL, Ellis WY, Ager AL, Anderaen SL, Gerena L, Milhous WK (1992) Bisquinolines. 1. N, N-bis(7-chloroquinolin-4-yl)alkanediamines with potential against chloroquine-resistant malaria. J Med Chem 35:2129–2134

    Article  CAS  PubMed  Google Scholar 

  • Villemagne B, Crauste C, Flipo M, Baulard MR, Déprez B, Willand N (2012) Tuberculosis: the drug development pipeline at a glance. Eur J Med Chem 51:1–16

    Article  CAS  PubMed  Google Scholar 

  • World Health Organization, Global tuberculosis report 2012, ISBN 978 92 4 1564502

Download references

Acknowledgments

The authors are thankful to the Head, Department of Chemistry, Sardar Patel University for providing 1H NMR, 13C NMR spectroscopy and research facilities. We are also thankful to DST, New Delhi for the assistance in general and for the PURSE central facility for mass spectrometry sponsored under PURSE program Grant vide sanction letter DO. No. SR/59/Z-23/2010/43,Vaibhav Laboratories, Ahmedabad, Gujarat, India for the FT-IR, SICART, Vallabh Vidyanagar, for elemental analysis and Dhanji P. Rajani, Microcare Laboratory, Surat, Gujarat, India for antimicrobial and antituberculosis screening of the compounds reported herein. One of the authors is grateful to UGC, New Delhi for Research Fellowship in Sciences for Meritorious Students.

Author information

Authors and Affiliations

  1. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, 388120, Gujarat, India

    Mehul B. Kanani & Manish P. Patel

Authors
  1. Mehul B. Kanani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Manish P. Patel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Manish P. Patel.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kanani, M.B., Patel, M.P. Design and synthesis of new (bis)trifluoromethyl-promoted N-aryl biquinoline derivatives as antitubercular and antimicrobial agents. Med Chem Res 24, 563–575 (2015). https://doi.org/10.1007/s00044-014-1140-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-014-1140-8

Keywords

Search

Navigation