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Synthesis and biological activity of (Z) and (E) isomers of 3-(3,4-diaryl-1,2,4-triazole-5-yl)prop-2-enoic acid

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Abstract

(Z)-3-(3,4-diaryl-1,2,4-triazole-5-yl)prop-2-enoic acid derivatives were obtained in the course of the reaction of N 3-substituted amidrazones with maleic anhydride, and isomerized into the (E) isomers by heating under reflux in acetic acid solution. The molecular structure of the compounds obtained was confirmed by IR and 1H NMR spectroscopy, and by X-ray crystallography for (2E)-3-(4,5-diphenyl-4H-1,2,4-triazol-3-yl)prop-2-enoic acid. The antiviral and immunomodulating activity of several of the compounds was examined.

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References

  1. O’Neil MJ, Heckelman PE, Koch CB, Roman KJ, Kenny CM, D’Arecca MR (eds) (2006) The Merck Index, 14th edn, entries 4881, 6417, 7506, 3081, 851. Merck, Whitehouse Station, NJ, USA

  2. Abdel-Hafez AA, Elsherief HA, Kurokawa M, Shiraki K, Kawahata T, Otake T, Nakamura N, Hattori M (2002) Arzneimittelforschung 52:833

    CAS  Google Scholar 

  3. Al-Soud YA, Al-Dwori MN, Al-Masoudi NA (2004) Farmaco 59:775

    Article  CAS  Google Scholar 

  4. De La Rosa M, Kim HW, Gunic E, Jenket C, Boyle U, Koh YH, Korboukh I, Allan M, Zhang W, Chen H, Xu W, Nilar S, Yao N, Hamatake R, Lang SA, Hong Z, Zhang Z, Giradet JL (2006) Bioorg Med Chem Lett 16:4444

    Article  Google Scholar 

  5. Zhou L, Amer A, Korn M, Burda R, Balzarini J, De Clercq E, Kern ER, Torrence PF (2005) Antivir Chem Chemother 16:375

    CAS  Google Scholar 

  6. Chun MW, Kim JH, Kim MJ, Kim BR, Jeong LS (2005) Nucleos Nucleot Nucleic Acids 24:979

    Article  CAS  Google Scholar 

  7. Tozkoparan B, Aktay G, Yesilada E (2002) Farmaco 57:145

    Article  CAS  Google Scholar 

  8. Labanauskas L, Udrenaite E, Gaidelis P, Brukstus A (2004) Farmaco 59:255

    Article  CAS  Google Scholar 

  9. Labanauskas L, Kalcas V, Undrenaite E, Gaidelis P, Brukstus A, Dauksas V (2001) Pharmazie 56:617

    CAS  Google Scholar 

  10. Novidopour L, Shafaroodi H, Abdi K, Amini M, Garemani MH, Dehpour AR, Shafiee A (2006) Bioorg Med Chem 14:2507

    Article  Google Scholar 

  11. Turan-Zitouni G, Kaplancikli ZA, Ozdemir A, Chevallet P, Kandilci HB, Gümüsel B (2007) Arch Pharm (Weinheim) 11:586

    Article  Google Scholar 

  12. Amir M, Kumar H, Javed SA (2007) Arch Pharm (Weinheim) 11:577

    Article  Google Scholar 

  13. Amir M, Kumar H, Javed SA (2007) Bioorg Med Chem Lett 16:4504

    Article  Google Scholar 

  14. Modzelewska-Banachiewicz B, Pyra E (1995/1996) Annales UMCS, Sec. AA, 50/51:111

    Google Scholar 

  15. Modzelewska-Banachiewicz B, Banachiewicz J, Chodkowska A, Jagiello-Wojtowicz E, Mazur L (2004) J Eur Med Chem 39:873

    Article  CAS  Google Scholar 

  16. Cysewski P, Modzelewska-Banachiewicz B (2004) Internet J Chem 7:2

    Google Scholar 

  17. Dugave C, Demange L (2003) Chem Rev 103:2475

    Article  CAS  Google Scholar 

  18. Zieliński W, Rajcy A (2000) Metody spektroskopowe i ich zastosowanie do identyfikacji związków organicznych WNT, Warszawa, p 571

  19. Miles EA, Allen E, Calder PC (2002) Cytokine 20:215

    Article  CAS  Google Scholar 

  20. Fiers W (1991) FEBS Lett 285:199

    Article  CAS  Google Scholar 

  21. Sheldrick GM (1997) SHELXS97. Program for a Crystal Structure Solution. University of Göttingen, Göttingen

    Google Scholar 

  22. Sheldrick GM (1997) SHELXL97. Program for the Refinement of a Crystal Structure from Diffraction Data. University of Göttingen, Göttingen

    Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Pharmacy, Nicolaus Copernicus University, Jagiellonska 13, 85-067, Bydgoszcz, Poland

    Bożena Modzelewska-Banachiewicz, Jacek Banachiewicz & Marzena Ucherek

  2. Department of Molecular Biology, Maria Curie-Sklodowska University, Akademicka 19, 20-033, Lublin, Poland

    Barbara Michalec

  3. Department of Immunology and Virology, Maria Curie-Sklodowska University, Akademicka 19, 20-033, Lublin, Poland

    Teresa Kamińska & Martyna Kandefer-Szerszeń

  4. Department of Crystallography, Maria Curie-Sklodowska University, M. Curie-Sklodowska Sq. 3, 20-031, Lublin, Poland

    Liliana Mazur & Anna E. Kozioł

Authors
  1. Bożena Modzelewska-Banachiewicz
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  2. Barbara Michalec
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  3. Teresa Kamińska
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  4. Liliana Mazur
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  5. Anna E. Kozioł
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  6. Jacek Banachiewicz
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  7. Marzena Ucherek
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  8. Martyna Kandefer-Szerszeń
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Correspondence to Barbara Michalec.

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Modzelewska-Banachiewicz, B., Michalec, B., Kamińska, T. et al. Synthesis and biological activity of (Z) and (E) isomers of 3-(3,4-diaryl-1,2,4-triazole-5-yl)prop-2-enoic acid. Monatsh Chem 140, 439–444 (2009). https://doi.org/10.1007/s00706-008-0055-9

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  • DOI: https://doi.org/10.1007/s00706-008-0055-9

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