Drug Res (Stuttg) 2014; 64(08): 420-423
DOI: 10.1055/s-0033-1361091
Original Article
© Georg Thieme Verlag KG Stuttgart · New York

Synthesis, Characterization and Antibacterial and Antifungal Evaluation of Some Para-Quinone Derivatives

A. M. Amani
1   Department of Chemistry, Shiraz University of Technology, Shiraz, Iran
› Author Affiliations
Further Information

Publication History

received 21 October 2013

accepted 04 November 2013

Publication Date:
27 November 2013 (online)

Abstract

Some novel Pyrrolo [2,3-f] Indole-3,7-Dicarbonitrile derivatives (1–5) were synthesized using chloranil, malononitrile and anilines. The structures of the newly synthesized compounds were characterized by elemental analysis, FT-IR, 1H- and 13C-NMR and mass spectroscopy. These compounds were screened for in vitro antibacterial and antifungal activities against some human pathogenic micro-organisms by employing the disc diffusion technique. Some of the compounds showed moderate to good biological activities when compared with standard drugs.

 
  • References

  • 1 Pratt YT, Drake NL. Quinolinequinones. V. 6-Chloro- and 7-chloro-5,8-quinolinequinones. J Am Chem Soc 1960; 82: 1155-1161
  • 2 David S, Chao Y, David R. NAD(P)H: quinone oxidoreductase 1 (NQO1) in the sensitivity and resistance to antitumor quinones. Biochem Pharmacol 2012; 83: 1033-1040
  • 3 Gaston ES, Maria EK, Marcos GD et al. Synthesis of steroidal quinones and hydroquinones from bile acids by Barton radical decarboxylation and benzoquinone addition. Studies on their cytotoxic and antifungal activities. Steroids 2012; 77: 45-51
  • 4 Tatjana B, Irena N, Miroslav JG et al. Synthesis and biological activity of derivatives of the marine quinone avarone. Eur J Med Chem 2010; 45: 923-929
  • 5 Vishnu KT, Hardesh KM, Manoj KV et al. ‘On water’ assisted synthesis and biological evaluation of nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents. Eur J Med Chem 2010; 45: 2418-2426
  • 6 Hyun-Jung L, Jin SK, Myung-Eun S et al. Synthesis and cytotoxicity evaluation of substituted pyridazino [4,5-b] phenazine -5,12-diones and tri/tetra-azabenzofluorene-5,6-diones. Eur J Med Chem 2007; 42: 168-174
  • 7 Ryu CK, Kang HY, Yi YJ et al. Synthesis and antifungal activities of 5/6-arylamino-4,7-dioxobenzithiazoles. Bioorg Med Chem Lett 2000; 10: 1589-1591
  • 8 Ryu CK, Song EH, Shim JY et al. Synthesis and antifungal activity of 2,5-disubstituted-6-arylamino-4,7-benzimidazolediones. Bioorg Med Chem Lett 2003; 13: 17-20
  • 9 Wellington KW, Kolesnikova NI. A laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity. Bioorg Med Chem Lett 2012; 20: 4472-4481
  • 10 Tandon VK, Yadav DB, Chaturvedi AK et al. Synthesis of (1,4)-naphthoquinono-[3,2-c]-1H-pyrazoles and their (1,4)-naphthohydroquinone derivatives as antifungal, antibacterial, and anticancer agents. Bioorg Med Chem Lett 2005; 15: 3288-3291
  • 11 Vishnu KT, Dharmendra BY, Hardesh KM et al. Design, synthesis, and biological evaluation of 1,2,3-trisubstituted-1,4-dihydrobenzo[g]quinoxaline-5,10-diones and related compounds as antifungal and antibacterial agents. Bioorg Med Chem 2006; 14: 6120-6126
  • 12 Hung SY, Chung KH, You HJ et al. Synthesis and biological evaluation of benzimidazole-4,7-diones that inhibit vascular smooth muscle cell proliferation. Bioorg Med Chem Lett 2004; 14: 3563-3566
  • 13 Brun MP, Braud E, Angotti D et al. Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity. Bioorg Med Chem 2005; 13: 4871-4878
  • 14 Kim YS, Park SY, Lee HJ et al. Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives. Bioorg Med Chem 2003; 11: 1709-1714
  • 15 Ryu CK, Lee JY, Jeong SH et al. Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles. Bioorg Med Chem Lett 2009; 19: 146-148
  • 16 Hammam AS, Abdel-Rahman MA, Hassan ARA et al. Synthesis and Characterization of Pyrrolo[2,3-f] Indole-3,7-Dicarbonitriles. Inter J Adv Med Sci 2013; 1: 11-17
  • 17 George S, Parameshwaran MK, Chakraborti AR et al. Synthesis and evaluation of the biological activities of some 3-{[5-6-methyl-4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3,4-oxadiazol-2-yl]-imino}-1,3-dihydro-2H-indol-2-one derivatives. Acta Pharma 2008; 58: 119-129
  • 18 Bauer AW, Kirby WM, Sherris JC et al. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 1996; 45: 493-496
  • 19 Kim JS, Rhee HK, Park HJ et al. Synthesis of 1-2-substituted-[1,2,3]triazolo[4,5-g]phthalazine-4,9-diones and evaluation of their cytotoxicity and topoisomerase II inhibition. Bioorg Med Chem 2008; 16: 4545-4550