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Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives

Year 2010, Volume: 14 Issue: 2, 84 - 90, 03.03.2014

Abstract

ABSTRACT: In this search, a series of 5-[4-(4-fluorobenzoylamino)phenyl]-2-substitutedamino-
1,3,4-thiadiazole ( 2a-g ) and 5-[4-(4-fluorobenzoylamino)phenyl]-4-substituted-2,4-dihydro-
3H-1,2,4-triazo-le-3-thione ( 3a-f ) derivatives were synthesized and characteristed by
elemental analysis, UV-visible, IR, 1H-NMR, MS spectral data and X-ray crystallograpy (3b).
Cytotoxic activity of six prototype compounds (2a, 2d, 2e, 3a, 3d and 3e) were evaluated by
using HeLa (ATCC CCL-2) and normal cell lines according to procedures of MTT
[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] Assay [Cell Proliferation Kit I
(MTT) Roche-Germany].
KEY WORDS: Cytotoxic activity, 1,2,4-triazoline-3-thione, 2,5-disubstituted-1,3,4-thiadiazole,
mtt assay, x-ray crystallograpy

References

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  • Foroumadi A, Soltani F, Moshafi MH, Ashraf-Askari R. Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl)piperazinylquinolone derivatives. Farmaco, 58: 1023-1028, 2003.
  • Thomasco LM, Gadwood RC, Weaver EA, Ochoada JM, Ford CW, Zurenko GE, Hamel JC, Stapert D, Moerman JK, Schaadt RD, Yagi BH. The synthesis and antibacterial activity of 1,3,4-thiadiazole phenyl oxazolidinone ana- logues. Bioorg Med Chem Lett, 13: 4193-4196, 2003.
  • Collin X, Sauleau A, Coulon J. 1,2,4-Triazolo mercapto and aminonitriles as potent antifungal agents. Bioorg Med Chem Lett, 13: 2601-2605, 2003.
  • Doğan HN, Duran A, Rollas S, Şener G, Uysal MK, Gülen D. Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimi- crobial activities. Bioorg Med Chem, 10: 2893-2898, 2002.
  • Rollas S, Yılmaz N, Erdeniz H, Kiraz M. Antimicrobial activities of some 5-(4-nitro/aminophenyl)-1, 2, 4- tria- zoline-3-thione derivatives. Med Sci Res, 26: 83-84,1998.
  • Oruç E, Rollas S, Kandemirli F, Shvets N, Dimoglo AS. 1,3,4-Thiadiazole Derivatives Synthesis, Structure Eluci- dation and Structure-Antitüberculosis Activity Relation- ships Investigations. J Med Chem, 47: 6760-6767, 2004.
  • Shiradkar MR, Murahari KK, Gangadasu HR, Suresh T, Kalyan CA, Panchal D, Kaur R, Burange P, Ghogare J, Mokale V, Raut M. Bioorg Med Chem, 15: 3997-4008, 2007.
  • Küçükgüzel I, Tatar E, Küçükgüzel ŞG, Rollas S, Clercq ED. Synthesis of some novel thiourea derivatives ob- tained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl- 2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur J Med Chem, 43: 381- 392, 2008.
  • Sharma S, Srivastava VK, Kumar A. Newer N-substitut- ed anthranilic acid derivatives as potent anti-inflamma- tory agents. Eur J Med Chem, 37: 689-697, 2002.
  • Palaska E, Şahin G, Kelicen P, Durlu NT, Altınok G. Syn- thesis and anti-inflammatory activity of 1-acylthiosemi- carbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Farmaco, 57: 101-107, 2002.
  • Vio L, Mamolo MG, Laneve A. Synthesis and antihy- pertensive activity of some 1,3,4-thiadiazole derivatives. Farmaco, 44: 165-172, 1988.
  • Idrees GA, AlyGamal OM, El-Din A.A. Abuo-Rahma G, Radwan MF. Design, synthesis and hypolipidemic activ- ity of novel 2-(naphtalen-2-yloxy)propionic acid deriva- tives as desmethyl fibrate analogs. Eur J Med Chem, 44: 3973-3980, 2009.
  • Mavrova AT, Wesselinova D, Tsenov YA, Denkova P. Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells. Eur J Med Chem, 44: 63-69, 2009.
  • Doğan HN, Duran A, Rollas S. Synthesis and preliminary anticancer activity of new 1H-4,5-dihydro-3-(3-hydroxy- 2-naphthyl)-4-substituted-1,2,4-triazoline-5-thiones. Part II. Indian J Chem, 44B: 2301-2307, 2005.
  • Holla BS, Veerendra B, Shivananda MK, Poojary B. Syn- thesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. Eur J Med Chem, 38: 759-767, 2003.
  • Rollas S, Kalyoncuoğlu N, Sür-Altıner D, Yeğenoğlu Y. 5-(4-Aminophenyl)-4- substituted-2,4-dihydro-3H-1,2,4- triazole-3-thiones : Synthesis and antibacterial and anti- fungal activities. Pharmazie, 48: 308-309, 1993.
  • Pospisil P, Ballmer P, Scapozza L, Folkers G. Tautom- erism in computer-aided drug design. J Recept Signal Transduct Res, 23: 361-371, 2003.
  • Durgun BB, Rollas S, Apaydın S, Öztürk R. Synthesis and antimicrobial activity of some new 1-[4-(4-fluoroben- zoylamino)benzoyl]-4-substitutedthiosemicarbazides. Drug Metab and Drug Interact, 12: 145-150, 1995.
  • Sharba AHK, Al-Bayati RH, Rezki N, Aouad MR. Syn- thesis of thiadiazoles and 1,2,4-triazoles derived from cy- clopropane dicarboxylic acid. Molecules, 10: 1153-1160, 2005.
  • Kubota S, Uda M. 1,2,4-Triazoles II. The tautomerism of 3-a-pyridyl-1,2,4-triazoline-5-thione and its methyl de- rivatives. Chem Pharm Bull, 20: 2096-2101, 1972.
  • Dobosz M, Pitucha M, Wujec M. The reactions of cycli- zation of thiosemicarbazide derivatives to 1,2,4-triazole or 1,3,4-thiadiazole system. Acta Pol. Pharm, 53: 31-38, 1996.
  • Rollas S. Synthesis and spectroscopic data of some 1,3,4-thiadiazoles. J Fac Pharm Istanbul, 17: 155-163, 1981.
  • Sheldrick GM. SHELXS-97, Program for solution of crys- tal structures, University of Göttingen, 1997.
  • Sheldrick GM. SHELXL-97, Program for solution of crys- tal structures, University of Göttingen, 1997.
  • Nardelli M. A system of Fortran routines for calculating molecular structure parameters from the results of crys- tal structure analyses. J Appl Cryst, 28: 659, 1995.
  • Farrugia LJ. WinGX suite for small-molecule single-crys- tal crystallography. J Appl Cryst, 32: 837, 1999.
  • Sgouras D, Duncan R. Methods for the Evaluation of Bio- compatibility of Soluble Synthetic Polymer Which have potential for Biomedical Use: 1-Use of the Tetrazolium- Based Colorimetric assay (MTT) As a Preliminary Screen for Evaluation of In Vitro Cytotoxicity. J Mater Sci Mater Med, 1: 61-68, 1990.

Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives

Year 2010, Volume: 14 Issue: 2, 84 - 90, 03.03.2014

Abstract

References

  • Foroumadi A, Mansouri S, Kiani Z, Rahmani A. Synthe- sis and in vitro antibacterial evaluation of N-[5-(5-nitro- 2-thienyl)-1,3,4-thiadiazole-2-yl]piperazinyl quinolones. Eur J Med Chem, 38: 851-854, 2003.
  • Foroumadi A, Soltani F, Moshafi MH, Ashraf-Askari R. Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl)piperazinylquinolone derivatives. Farmaco, 58: 1023-1028, 2003.
  • Thomasco LM, Gadwood RC, Weaver EA, Ochoada JM, Ford CW, Zurenko GE, Hamel JC, Stapert D, Moerman JK, Schaadt RD, Yagi BH. The synthesis and antibacterial activity of 1,3,4-thiadiazole phenyl oxazolidinone ana- logues. Bioorg Med Chem Lett, 13: 4193-4196, 2003.
  • Collin X, Sauleau A, Coulon J. 1,2,4-Triazolo mercapto and aminonitriles as potent antifungal agents. Bioorg Med Chem Lett, 13: 2601-2605, 2003.
  • Doğan HN, Duran A, Rollas S, Şener G, Uysal MK, Gülen D. Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimi- crobial activities. Bioorg Med Chem, 10: 2893-2898, 2002.
  • Rollas S, Yılmaz N, Erdeniz H, Kiraz M. Antimicrobial activities of some 5-(4-nitro/aminophenyl)-1, 2, 4- tria- zoline-3-thione derivatives. Med Sci Res, 26: 83-84,1998.
  • Oruç E, Rollas S, Kandemirli F, Shvets N, Dimoglo AS. 1,3,4-Thiadiazole Derivatives Synthesis, Structure Eluci- dation and Structure-Antitüberculosis Activity Relation- ships Investigations. J Med Chem, 47: 6760-6767, 2004.
  • Shiradkar MR, Murahari KK, Gangadasu HR, Suresh T, Kalyan CA, Panchal D, Kaur R, Burange P, Ghogare J, Mokale V, Raut M. Bioorg Med Chem, 15: 3997-4008, 2007.
  • Küçükgüzel I, Tatar E, Küçükgüzel ŞG, Rollas S, Clercq ED. Synthesis of some novel thiourea derivatives ob- tained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl- 2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur J Med Chem, 43: 381- 392, 2008.
  • Sharma S, Srivastava VK, Kumar A. Newer N-substitut- ed anthranilic acid derivatives as potent anti-inflamma- tory agents. Eur J Med Chem, 37: 689-697, 2002.
  • Palaska E, Şahin G, Kelicen P, Durlu NT, Altınok G. Syn- thesis and anti-inflammatory activity of 1-acylthiosemi- carbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Farmaco, 57: 101-107, 2002.
  • Vio L, Mamolo MG, Laneve A. Synthesis and antihy- pertensive activity of some 1,3,4-thiadiazole derivatives. Farmaco, 44: 165-172, 1988.
  • Idrees GA, AlyGamal OM, El-Din A.A. Abuo-Rahma G, Radwan MF. Design, synthesis and hypolipidemic activ- ity of novel 2-(naphtalen-2-yloxy)propionic acid deriva- tives as desmethyl fibrate analogs. Eur J Med Chem, 44: 3973-3980, 2009.
  • Mavrova AT, Wesselinova D, Tsenov YA, Denkova P. Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells. Eur J Med Chem, 44: 63-69, 2009.
  • Doğan HN, Duran A, Rollas S. Synthesis and preliminary anticancer activity of new 1H-4,5-dihydro-3-(3-hydroxy- 2-naphthyl)-4-substituted-1,2,4-triazoline-5-thiones. Part II. Indian J Chem, 44B: 2301-2307, 2005.
  • Holla BS, Veerendra B, Shivananda MK, Poojary B. Syn- thesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. Eur J Med Chem, 38: 759-767, 2003.
  • Rollas S, Kalyoncuoğlu N, Sür-Altıner D, Yeğenoğlu Y. 5-(4-Aminophenyl)-4- substituted-2,4-dihydro-3H-1,2,4- triazole-3-thiones : Synthesis and antibacterial and anti- fungal activities. Pharmazie, 48: 308-309, 1993.
  • Pospisil P, Ballmer P, Scapozza L, Folkers G. Tautom- erism in computer-aided drug design. J Recept Signal Transduct Res, 23: 361-371, 2003.
  • Durgun BB, Rollas S, Apaydın S, Öztürk R. Synthesis and antimicrobial activity of some new 1-[4-(4-fluoroben- zoylamino)benzoyl]-4-substitutedthiosemicarbazides. Drug Metab and Drug Interact, 12: 145-150, 1995.
  • Sharba AHK, Al-Bayati RH, Rezki N, Aouad MR. Syn- thesis of thiadiazoles and 1,2,4-triazoles derived from cy- clopropane dicarboxylic acid. Molecules, 10: 1153-1160, 2005.
  • Kubota S, Uda M. 1,2,4-Triazoles II. The tautomerism of 3-a-pyridyl-1,2,4-triazoline-5-thione and its methyl de- rivatives. Chem Pharm Bull, 20: 2096-2101, 1972.
  • Dobosz M, Pitucha M, Wujec M. The reactions of cycli- zation of thiosemicarbazide derivatives to 1,2,4-triazole or 1,3,4-thiadiazole system. Acta Pol. Pharm, 53: 31-38, 1996.
  • Rollas S. Synthesis and spectroscopic data of some 1,3,4-thiadiazoles. J Fac Pharm Istanbul, 17: 155-163, 1981.
  • Sheldrick GM. SHELXS-97, Program for solution of crys- tal structures, University of Göttingen, 1997.
  • Sheldrick GM. SHELXL-97, Program for solution of crys- tal structures, University of Göttingen, 1997.
  • Nardelli M. A system of Fortran routines for calculating molecular structure parameters from the results of crys- tal structure analyses. J Appl Cryst, 28: 659, 1995.
  • Farrugia LJ. WinGX suite for small-molecule single-crys- tal crystallography. J Appl Cryst, 32: 837, 1999.
  • Sgouras D, Duncan R. Methods for the Evaluation of Bio- compatibility of Soluble Synthetic Polymer Which have potential for Biomedical Use: 1-Use of the Tetrazolium- Based Colorimetric assay (MTT) As a Preliminary Screen for Evaluation of In Vitro Cytotoxicity. J Mater Sci Mater Med, 1: 61-68, 1990.
There are 28 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Sevgi Karakuş

Ufuk Çoruh This is me

Bilgehan Barlas-durgun This is me

Ezequiel Vázquez-lópez This is me

Suna Özbaş-turan This is me

Jülide Akbuğa This is me

Sevim Rollas This is me

Publication Date March 3, 2014
Published in Issue Year 2010 Volume: 14 Issue: 2

Cite

APA Karakuş, S., Çoruh, U., Barlas-durgun, B., Vázquez-lópez, E., et al. (2014). Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives. Marmara Pharmaceutical Journal, 14(2), 84-90. https://doi.org/10.12991/mpj.87064
AMA Karakuş S, Çoruh U, Barlas-durgun B, Vázquez-lópez E, Özbaş-turan S, Akbuğa J, Rollas S. Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives. Marmara Pharm J. March 2014;14(2):84-90. doi:10.12991/mpj.87064
Chicago Karakuş, Sevgi, Ufuk Çoruh, Bilgehan Barlas-durgun, Ezequiel Vázquez-lópez, Suna Özbaş-turan, Jülide Akbuğa, and Sevim Rollas. “Synthesis and Cytotoxic Activity of Some 1,2,4-Triazoline-3-Thione and 2,5-Disubstituted- 1,3,4-Thiadiazole Derivatives”. Marmara Pharmaceutical Journal 14, no. 2 (March 2014): 84-90. https://doi.org/10.12991/mpj.87064.
EndNote Karakuş S, Çoruh U, Barlas-durgun B, Vázquez-lópez E, Özbaş-turan S, Akbuğa J, Rollas S (March 1, 2014) Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives. Marmara Pharmaceutical Journal 14 2 84–90.
IEEE S. Karakuş, U. Çoruh, B. Barlas-durgun, E. Vázquez-lópez, S. Özbaş-turan, J. Akbuğa, and S. Rollas, “Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives”, Marmara Pharm J, vol. 14, no. 2, pp. 84–90, 2014, doi: 10.12991/mpj.87064.
ISNAD Karakuş, Sevgi et al. “Synthesis and Cytotoxic Activity of Some 1,2,4-Triazoline-3-Thione and 2,5-Disubstituted- 1,3,4-Thiadiazole Derivatives”. Marmara Pharmaceutical Journal 14/2 (March 2014), 84-90. https://doi.org/10.12991/mpj.87064.
JAMA Karakuş S, Çoruh U, Barlas-durgun B, Vázquez-lópez E, Özbaş-turan S, Akbuğa J, Rollas S. Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives. Marmara Pharm J. 2014;14:84–90.
MLA Karakuş, Sevgi et al. “Synthesis and Cytotoxic Activity of Some 1,2,4-Triazoline-3-Thione and 2,5-Disubstituted- 1,3,4-Thiadiazole Derivatives”. Marmara Pharmaceutical Journal, vol. 14, no. 2, 2014, pp. 84-90, doi:10.12991/mpj.87064.
Vancouver Karakuş S, Çoruh U, Barlas-durgun B, Vázquez-lópez E, Özbaş-turan S, Akbuğa J, Rollas S. Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives. Marmara Pharm J. 2014;14(2):84-90.