Drug Res (Stuttg) 2013; 63(02): 53-59
DOI: 10.1055/s-0032-1331711
Original Article
© Georg Thieme Verlag KG Stuttgart · New York

Synthesis, Spectral Characterization and Antimicrobial Activity of Substituted Thiazolyl Derivatives of 2-Quinolones

M. S. Katagi
1   Bapuji Pharmacy College, Karnataka, India
G. S. Bolakatti
1   Bapuji Pharmacy College, Karnataka, India
A. M. Badiger
2   Shree Dhanvantary Pharmaceutical Analysis and Research Centre, Kim (E), Gujarat, India
D. Satyanarayana
3   Department of Pharmaceutical Chemistry, N G S M Institute of Pharmaceutical Sciences, Karnataka, India
S. N. Mamledesai
4   PES College of pharmacy and Research, Goa, India
M. L. Sujatha
5   Bapuji Institute Of Engineering and Technology, Karnataka, India
› Author Affiliations
Further Information

Publication History

received 10 May 2012

accepted 20 November 2012

Publication Date:
20 February 2013 (online)


A series of new 3-(2-substituted amino/substituted hydrazino-1,3-thiazol-4-yl)-4-hydroxy-1-methyl/phenylquinolin-2 (1H)-one hydroiodide 3a–3f and 4a–4f derivatives were prepared by heating 3-Acetyl-4-hydroxy-1-methyl/phenyl quinolin-2 (1H)-one 2a–2b with substituted thiourea and substituted thiosemicarbazide in presence of iodine in n-butanol. The title compounds were characterized on the basis of IR, 1H NMR, 13C NMR and Mass spectral (MS) studies. Further title compounds were evaluated for antibacterial and antifungal by Agar diffusion assay method where as antitubercular activity by Micro-plate Alamar Blue Assay (MABA). Among 12 synthesized novel compounds 3a, 3b, 4d exhibited promising antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. 3a, 3b, 3e, 4d, 4e showed good antifungal activity against Candida albicans and Aspergillus niger. 3a, 3d, 4d showed good antitubercular activity against Mycobacterium tuberculosis H37Rv strain.

  • References

  • 1 Javetz E, Melnick JL, Adelberg EA. In: Review of Medical Microbiology. Lange; California: 1984: 122
  • 2 World Health Organization (Switzerland) . Global Tuberculosis Control 2009: Epidemiology, Stratey, Financing; WHO Report 2009, WHO Library Cataloguing-in-Publication Data. World Health Organization; Geneva, Switzerland: 2009
  • 3 Thomas K. The pyrano route to 4-hydroxy-2-quinolone and 4-hydroxy-2-pyridones. IL farmaco 1999; 54: 309-315
  • 4 Girish B, Manjunatha SK, Mamledesai SN et al. Synthesis and antimicrobial activity of 4-hydroxy-1 methyl/phenyl-3- (substituted anilinoacetyl) quinolin-2(1H)-one. RGUHS J Pharm Sci 2012; 02: 60-66
  • 5 Joseph P, Charles B, Gladys D et al. Refomatsky reactions with N-arylpyrrolidine-2-thiones: Synthesis of tricyclic analogues of quinolone antibacterial agents. Tetrahedron 2001; 57: 9635-9648
  • 6 El-Dine SA, El-Khawass SM. Synthesis of 4-[(2-alkylaryl or arylalkyl) amino-1,3,4-thiadiazol-5-yl]-2-synthesized quinolines and compounds reasonable antifungal and antimicrobial activity. Pharmazie 1979; 34: 537-538
  • 7 Anastasia D, Dionysia B, Kyriakos CP et al. Design and synthesis of novel quinolinone-3-aminoamides and their α-lipoic acid adducts as antioxidant and anti-inflammatory agents. J Med Chem 2007; 50: 2450-2458
  • 8 Joseph S, Francis D. Aryl-2-quinolone derivatives having in vivo and in vitro antitumour activity. J Med Chem 2002; 45: 2543
  • 9 Qun LI, Keith WW, Weibo W et al. Design, synthesis, and activity of achiral analogs of 2-quinolones and indoles as non-thiol farnesyltransferase inhibitors. Bioorg Med Chem Lett 2005; 15: 2033-2039
  • 10 Gisela CM, Mariela B, Ana MB et al. Evaluation of antiparasitic, antituberculosis and antiangiogenic activities of 3-aminoquinolin-2-one derivatives. J Chil Chem Soc 2006; 51: 859-863
  • 11 Rulin Z, Stacey G, Joseph ES et al. A new facile synthesis of 2-aminothiazol-5-corboxylates. Tetrahedron Lett 2001; 42: 2101-2102
  • 12 Handan A, Oznur A, Seher B et al. Synthesis of Mannich bases of some 2,5-disubstituted-4-thiazolidinones and evaluation of their antimicrobial activities. Turk J Chem 2005; 29: 425-435
  • 13 Mitsuo K, Tadashi A, Yoshitada S. One pot synthesis of 2-aminothiazoles using supported reagents. Tetrahedron Lett 2002; 43: 1717-1720
  • 14 Wolfson J, Hooper DC. Fluoroquinolone Antimicrobial agents. Clini Microbio Rev 1989; 2: 378-424
  • 15 Hooper DC. Quinolones. In: Mandell GL, Bennett JE, Dolin R. (eds.). Mandell, Douglas and Bennett’s principles and practice of infectious diseases. 4th edition. New York: Churchill Livingstone Inc.; 1995: 364-375
  • 16 Hooper DC. Clinical applications of quinolones. Biochim Biophys Acta 1998; 45-61
  • 17 Hardman JG, Limbird EL, Molinoff PB et al. Goodman & Gilman’s, The Pharmacological Basis of Therapeutics. 9th edition. McGraw-Hill Publication; 2002: 1065
  • 18 Anquetin G, Greiner J, Mahmoudi N et al. Design, synthesis and activity against Toxoplasma gondii, Plasmodium spp., and Mycobacterium tuberculosis of new 6-fluoroquinolones. Eur J Med Chem 2006; 41: 1478-1493
  • 19 Janin YL. Antituberculosis drugs: Ten years of research. Bioorg Med Chem 2007; 15: 2479-2513
  • 20 Sriram D, Yogeeswari P, Basha JS et al. Synthesis and antimycobacterial evaluation of various 7-substituted ciprofloxacin derivatives. Bioorg Med Chem 2005; 13: 5774-5778
  • 21 Ginsburg AS, Grosset JH, Bishai WR. Fluoroquinolones, tuberculosis, and resistance. Lancet Infect Dis 2003; 3: 432-442
  • 22 Alexandra A, Veziris N, Cambau E et al. Novel Gyrase Mutations in Quinolone-Resistant and Hyper susceptible Clinical Isolates of Mycobacterium tuberculosis: Functional Analysis of Mutant Enzymes. Antimicrobial Agents and Chemother 2006; 50: 04-112
  • 23 Cheng AF, Yew WW, Chan EW et al. Multiplex PCR amplimer conformation analysis for rapid detection of gyrA mutations in fluoroquinolone-resistant Mycobacterium tuberculosis clinical isolates. Antimicrobial Agents and Chemother 2004; 48: 596
  • 24 Roschger P, Fiala W, Sradlabauern W. Nucleophilic substitution and ringclosure reactions of 4-chloro-3-nitro-2-quinolones. J Heterocycl Chem 1992; 29: 225-231
  • 25 Miguel JG, Rachel ML, Susan LM et al. Synthesis and evaluation of substituted 4-aryloxy and 4-arylsulfanylphenyl-2-aminothiazoles as inhibitors of human breast cancer cell proliferation. Bioorg Med Chem 2004; 12: 1029-1036
  • 26 Fairbrother RW, Martyn G. The Disc Technique for Determining Sensitivity to the Antibiotics. J Clin Pathol 1951; 4: 374-377
  • 27 Gould JC, Bowie JH. The determination of bacterial sensitivity to antibiotics. Edinb Med J 1952; 59: 178-199
  • 28 Katritzky R, Rachal S. New routes to selectively methylated benzimidazoles. J Heterocycl Chem 1994; 31: 775
  • 29 Franzblau SG, Witzig RS, McLaughlin JC et al. Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol 1998; 36: 362-366