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Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones

Year 2013, Volume: 17 Issue: 2, 147 - 154, 07.03.2014

Görkem Ermut Nilgün Karalı İdil Çetin Mehmet Topçul Seher Birteksöz

Abstract

Keywords

Anticancer activity antiviral activity antimicrobial activity 5-chloro-1H- indole-2 3-dione thiosemicarbazone

References

  • Heffeter P, Pirker C, Kowol CR, Herrman G, Dornetshuber R, Miklos W, Jungwirth U, Koellensperger G, Keppler BK, Berger W. Phase I and pharmacodynamic study of Triapine®, a novel ribonucleotide reductase inhibitor, in patients with advanced leukemia. Leuk Res 2003;27:1077-83.
  • Neyts J, De Clercq E. Therapy and short-term prophylaxis of poxvirus infections: historical background and perspectives. Antiviral Res 2003;57:25-33.
  • Ronen D, Teitz Y. Inhibition of the synthesis of Moloney leukemia virus structural proteins by N-methylisatinβ-4’,4’diethylthiosemicarbazone, Antimicrob Agents Chemother 1984;26:913-6.
  • Pandeya SN, Smitha S, Jyoti M, Sridhar S. Biological activities of isatin and its derivatives. Acta Pharm 2005;55:27-46.
  • Vine KL, Matesic L, Locke JM, Ranson M, Skropeta D. Cytotoxic and anticancer activities of isatin and its derivatives: A Comprehensive Review from 2000-2008 AntiCancer Agents. Med Chem 2009;9:397-414.
  • Pandeya SN; Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti-HIV evaluation of Norfloxacin Mannich bases. Sci Pharm 1999;67:103-11.
  • Karalı N. Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives. Eur J Med Chem 2002;37:909-18.
  • Karalı N, Gürsoy A, Kandemirli F, Shvetsc N, Kaynak FB, Özbey S, Kovalishyne V, Dimoglo A. Synthesis and structure–antituberculosis activity relationship of 1H-indole-2,3dione derivatives. Bioorg Med Chem 2007;15:5888-904.
  • Güzel Ö, Karalı N, Salman, A. Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives. Bioorg Med Chem 2008;16:8976-87.
  • Hall MD, Salam NK, Hellawell JL, Fales HM, Kensler CB, Ludwig JA, Szakács G, Hibbs DE, Gottesman MM. Synthesis, Activity, and Pharmacophore Development for Isatin-β-thiosemicarbazones with Selective Activity toward Multidrug-Resistant Cells. J Med Chem 2009;52:3191-204.
  • Hall MD, Brimacombe KR, Varonka MS, Pluchino KM, Monda JK, Li J, Walsh MJ, Boxer MB, Warren TH, Fales HM, Gottesman MM. Synthesis and structure–activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein. J Med Chem 2011;54:5878-89. Patil SA, Naik VH, Kulkarni AD, Badami PS. Spectroscopic, DNA cleavage and antimicrobial studies of Co(II), Ni(II) and Cu(II) complexes of sulfur donor schiff bases. J Sulfur Chem 2010;31:109-21.
  • Wang J, Lixin Z, Zhengming L, Huanqin D, Weimin W, Fuxing S, Haizhong T, Hui G. Indole satisfies diketone derivatives thereof in preparing drug resistance of the super bacteria medicine the application of. Eur Patent CN102464603A, 2012 May 23.
  • Arıcan GÖ, Topçul M. Effect of epirubicin on mitotic index in cultured L-cells. J Cell Mol Biol 2003;2:43-8. increase in inhibitory activity against S. aureus and C. albicans. In conclusion, structural modification may lead to new derivatives with high selectivity for a range of human cancer cell lines, various bacteria and viruses. ACKNOWLEDGEMENTS
  • We thank Prof. Lieve Naesens from the Rega Institute for Medical Research, Katholieke Universiteit, Leuven, Belgium for evaluation of anviral activity. This work was supported by Istanbul University Scientific Research Projects. Project Number: BYP-15286

Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones

Year 2013, Volume: 17 Issue: 2, 147 - 154, 07.03.2014

Görkem Ermut Nilgün Karalı İdil Çetin Mehmet Topçul Seher Birteksöz

Abstract

References

  • Heffeter P, Pirker C, Kowol CR, Herrman G, Dornetshuber R, Miklos W, Jungwirth U, Koellensperger G, Keppler BK, Berger W. Phase I and pharmacodynamic study of Triapine®, a novel ribonucleotide reductase inhibitor, in patients with advanced leukemia. Leuk Res 2003;27:1077-83.
  • Neyts J, De Clercq E. Therapy and short-term prophylaxis of poxvirus infections: historical background and perspectives. Antiviral Res 2003;57:25-33.
  • Ronen D, Teitz Y. Inhibition of the synthesis of Moloney leukemia virus structural proteins by N-methylisatinβ-4’,4’diethylthiosemicarbazone, Antimicrob Agents Chemother 1984;26:913-6.
  • Pandeya SN, Smitha S, Jyoti M, Sridhar S. Biological activities of isatin and its derivatives. Acta Pharm 2005;55:27-46.
  • Vine KL, Matesic L, Locke JM, Ranson M, Skropeta D. Cytotoxic and anticancer activities of isatin and its derivatives: A Comprehensive Review from 2000-2008 AntiCancer Agents. Med Chem 2009;9:397-414.
  • Pandeya SN; Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti-HIV evaluation of Norfloxacin Mannich bases. Sci Pharm 1999;67:103-11.
  • Karalı N. Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives. Eur J Med Chem 2002;37:909-18.
  • Karalı N, Gürsoy A, Kandemirli F, Shvetsc N, Kaynak FB, Özbey S, Kovalishyne V, Dimoglo A. Synthesis and structure–antituberculosis activity relationship of 1H-indole-2,3dione derivatives. Bioorg Med Chem 2007;15:5888-904.
  • Güzel Ö, Karalı N, Salman, A. Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives. Bioorg Med Chem 2008;16:8976-87.
  • Hall MD, Salam NK, Hellawell JL, Fales HM, Kensler CB, Ludwig JA, Szakács G, Hibbs DE, Gottesman MM. Synthesis, Activity, and Pharmacophore Development for Isatin-β-thiosemicarbazones with Selective Activity toward Multidrug-Resistant Cells. J Med Chem 2009;52:3191-204.
  • Hall MD, Brimacombe KR, Varonka MS, Pluchino KM, Monda JK, Li J, Walsh MJ, Boxer MB, Warren TH, Fales HM, Gottesman MM. Synthesis and structure–activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein. J Med Chem 2011;54:5878-89. Patil SA, Naik VH, Kulkarni AD, Badami PS. Spectroscopic, DNA cleavage and antimicrobial studies of Co(II), Ni(II) and Cu(II) complexes of sulfur donor schiff bases. J Sulfur Chem 2010;31:109-21.
  • Wang J, Lixin Z, Zhengming L, Huanqin D, Weimin W, Fuxing S, Haizhong T, Hui G. Indole satisfies diketone derivatives thereof in preparing drug resistance of the super bacteria medicine the application of. Eur Patent CN102464603A, 2012 May 23.
  • Arıcan GÖ, Topçul M. Effect of epirubicin on mitotic index in cultured L-cells. J Cell Mol Biol 2003;2:43-8. increase in inhibitory activity against S. aureus and C. albicans. In conclusion, structural modification may lead to new derivatives with high selectivity for a range of human cancer cell lines, various bacteria and viruses. ACKNOWLEDGEMENTS
  • We thank Prof. Lieve Naesens from the Rega Institute for Medical Research, Katholieke Universiteit, Leuven, Belgium for evaluation of anviral activity. This work was supported by Istanbul University Scientific Research Projects. Project Number: BYP-15286
There are 14 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Görkem Ermut This is me

Nilgün Karalı This is me

İdil Çetin This is me

Mehmet Topçul This is me

Seher Birteksöz This is me

Publication Date March 7, 2014
Published in Issue Year 2013 Volume: 17 Issue: 2

Cite

APA Ermut, G., Karalı, N., Çetin, İ., Topçul, M., et al. (2014). Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones. Marmara Pharmaceutical Journal, 17(2), 147-154. https://doi.org/10.12991/201317383
AMA Ermut G, Karalı N, Çetin İ, Topçul M, Birteksöz S. Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones. Marmara Pharm J. October 2014;17(2):147-154. doi:10.12991/201317383
Chicago Ermut, Görkem, Nilgün Karalı, İdil Çetin, Mehmet Topçul, and Seher Birteksöz. “Synthesis and Chemotherapeutic Activities of 5-Chloro-1H-Indole-2,3-Dione 3-Thiosemicarbazones”. Marmara Pharmaceutical Journal 17, no. 2 (October 2014): 147-54. https://doi.org/10.12991/201317383.
EndNote Ermut G, Karalı N, Çetin İ, Topçul M, Birteksöz S (October 1, 2014) Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones. Marmara Pharmaceutical Journal 17 2 147–154.
IEEE G. Ermut, N. Karalı, İ. Çetin, M. Topçul, and S. Birteksöz, “Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones”, Marmara Pharm J, vol. 17, no. 2, pp. 147–154, 2014, doi: 10.12991/201317383.
ISNAD Ermut, Görkem et al. “Synthesis and Chemotherapeutic Activities of 5-Chloro-1H-Indole-2,3-Dione 3-Thiosemicarbazones”. Marmara Pharmaceutical Journal 17/2 (October 2014), 147-154. https://doi.org/10.12991/201317383.
JAMA Ermut G, Karalı N, Çetin İ, Topçul M, Birteksöz S. Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones. Marmara Pharm J. 2014;17:147–154.
MLA Ermut, Görkem et al. “Synthesis and Chemotherapeutic Activities of 5-Chloro-1H-Indole-2,3-Dione 3-Thiosemicarbazones”. Marmara Pharmaceutical Journal, vol. 17, no. 2, 2014, pp. 147-54, doi:10.12991/201317383.
Vancouver Ermut G, Karalı N, Çetin İ, Topçul M, Birteksöz S. Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones. Marmara Pharm J. 2014;17(2):147-54.