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The Chemistry of Formazans and Tetrazolium Salts

Year 2012, Volume: 40 Issue: 3, 293 - 301, 01.08.2012
https://izlik.org/JA73HA24BD

Abstract

In this rewiev, the structure of formazans and of tetrazolium salts has been described. Furthermore, importance and usage of formazan-tetrazolyum systems have been explained. Tautomerization properties and geometric isomers based on conjugate π-system of formazans have been examined. In addition, common synthesis of these compounds and UV-visible, IR, 1H NMR spectrums used in explanation of structures have been discussed.

References

  • 1. HV. Pechmann, P. Runge, Oxidation der Formazylverbindungen II, Ber. Deutsch. Chem. Ges. 27 (1894) 2920.
  • 2. GH. Findlay, The value of some tetrazolium salts as histochemical reagents for sulphydryl groups, J. Histochem. Cytochem. 3 (1955) 331.
  • 3. E. Koren, R. Kohen, I. Gınsburg, A CobaltBased Tetrazolium Salts Reduction Test to Assay Polyphenols J. Agric. Food Chem., 57 (2009) 7644.
  • 4. E. Seidler, The tetrazolium- Formazan System, Prog. in Histochem. and Cytochem. 24 (1991) 1.
  • 5. R. Kuhn, D. Jerchel, Reduktion von Tetrazoliumsalzen durch Bakterier garende Hefe und keimende Samen., Ber. Deutsch. Chem. Ges. 74 (1941) 949.
  • 6. AN Babu, RR. Nadendla, Synthesis of some new quinazolinone formazans as anti-Inflammatory and anthelmintic agents, J. of Pharm. Res. 4 (2011) 983.
  • 7. W. Reid, Formazane und Tetrazoliumsalze, ihre Synthesen und ihre Bedeutung als Reduktionsindikatoren und Vitalfarbstoffe, Angew. Chem. 64 (1951) 391.
  • 8. JA. Plumb, R. Milroy, SB. Kaye, Effects of the pH Dependence of 3-(4,5- Dimethylthiazol-2-yl)-2,5- diphenyltetrazoliumBromide-Formazan, Cancer Res 49 (1989) 4435.
  • 9. H. Tezcan, N. Özkan, Substituent effects on the spectral properties of some 3-substituted Formazans, Dyes and Pigments 56 (2003) 159.
  • 10. H. Wan, R. Williams, P. Doherty, DF. Williams, The cyctotoxicity evaluation of Kevlar and Silicon Carbide by MMT assay, J. Mat. Sci. Mat. Med. 5 (1994) 154.
  • 11. FP. Altman, Tetrazolium salts and formazans. Prog. Histochem. Cytochem. 9 (1976) 1.
  • 12. J P. Raval, PR. Patel, NH. Patel, PS. Patel, Synthesis, Characeterization and in vitro antibacterial activity of novel 3-(4-methoxyphenyl)-1-isonicotinoyl5-(substituted phenyl)-formazans, Inter. J. of ChemTech Res. 1, No.3 (2009) 610.
  • 13. JP. Raval, PR. Patel, PS. Patel, In vitro Antitubercular activity of novel 3-(4- Methoxyphenyl)-1- isonicotinoyl-5-(substituted phenyl)-formazans, Inter. J. of ChemTech Res. 1 No.4 1548.
  • 14. S. Hunig, O. Boes, Beitrage zur substituentenwirkung, Liebigs Ann. Chem. 28 (1953) 579.
  • 15. AW. Nineham, The Chemistry of Formazans and Tetrazolium Salts, Chem. Rev. 55 (1955) 355.
  • 16. H. Tezcan, ML. Aksu, Electrochemical properties of 1-(o,m,p-nitrophenyl)-3- (m−nitro phenyl)-5- phenylformazans and their nickel complexes, Turk J Chem 34 (2010) 465.
  • 17. FR. Besson, W. Hartzell, WL. Savell, 1-(3,4-Dimethylphenyl)-5-methyltetrazole, J. Am. Chem. Soc. 73 (1951) 4457.
  • 18. L. Hunter, CB. Roberts, Associating effect of the hydrogen atom. IX. The N-H bond. Virtual tautomerism of the formazyl compounds, J. Chem. Soc. (1941) 820.
  • 19. I. Hausser, D. Jerchel, R. Kuhn, The red-yellow rearrangement of formazans by light Chem. Ber. 82 (1949) 515.
  • 20. GI. Sigeikin, GN. Lipunova, IG.Pervova, Formazans and their metal complexes, Russ. Chem. Rev. 75 (2006) 885.
  • 21. G. Buemi, F. Zuccarello, P. Venuvanalingam, M. Ramalingam, SS. Ammal, Ab initio study of formazan and 3-nitroformazan, J. Chem. Soc., Faraday Trans. 94 (1998) 3313.
  • 22. H. Tezcan, E. Uzluk, The synthesis and spectral properties determination of 1,3-substituted phenyl5-phenylformazans, Dyes and Pigments 75 (2007) 633.
  • 23. NA. Frolova, SZ. Vatsadze, NY. Vetokhina, VE. Zavodnik, NV. Zyk, New C-arylation reaction found during a study on the interaction of aldo hydrazones and arenediazonium chlorides, Mendeleev Commun., 16 (2006) 251.
  • 24. KG. Desai, KR. Desai, Microbial screening of novel synthesized formazans having amide linkages, J. of Heterocyc. Chem. 43 (2006) 1083.
  • 25. G. Mariappan, R. Korim et al, Synthesis and biological evaluation of formazan derivatives, J. Adv. Pharm. Tecn.& Res. 1 (2010) 396.
  • 26. VZ. Mady, I. Pinter, MP. Kajtar, A. Perczel, Transformation of aldose formazans, Novel synthesis of 2-acetamido-2-deoxypentonolactones and a new pent-2-enose formazan, Carbohydrate Research 346 (2011) 1534.
  • 27. H. Tezcan, Synthesis and spectral properties of some bis-substituted formazans, Spectrochim. Acta Part A 69 (2008) 971.
  • 28. YA. Ibrahim, AHM. Elwahy, AA. Abbas, New synthesis of macrocyclic crown-formazans from pyruvic acid derivatives, Tetrahedron 50 39 (1994) 11489.
  • 29. M. Ishiyama, M. Shiga, et al., A new sulfonated tetrazolium salts, Chem. Pharm. Bull. 41 6 (1993) 1118.
  • 30. M. Ishiyama, Y. Miyazono, et al., A highly watersoluble disulfonated tetrazolium salts, Talanta 44 (1997) 1299.
  • 31. OE. Sherif, Effect of solvents on the electronic absorption spectra of some substituted diarylformazans, Monat. Für Chem 128 (1997) 981.
  • 32. JW. Lewis, C. Sandfory, Infrared absorption and resonance Raman scattering of Photochromic triphenylformazans, J. Chem. 61 (1983) 809.
  • 33. AA. Abbas and AHM. Elwahy, Synthesis of spirolinked macrocyclic crown formazans and a bis(crown formazan), Arkivoc x (2009) 65.

Formazanlar ve Tetrazolyum Tuzlarının Kimyası

Year 2012, Volume: 40 Issue: 3, 293 - 301, 01.08.2012
https://izlik.org/JA73HA24BD

Abstract

B u çalışmada tetrazolyum tuzları veformazanların yapıları tanımlanmıştır. Ayrıca formazan-tetrazolyum sistemlerinin önemi ve kullanım alanları açıklanmıştır. Formazanların sahip oldukları conjugate p-system kaynaklanan tautomerleşme özellikleri ve geometrik izomerleri incelenmiştir. Bu bileşiklerin en yaygın kullanılan sentezleri ve yapılarının açıklanmasında önemli olan UV-visible, IR ve 1H NMR spektrumları tartışılmıştır

References

  • 1. HV. Pechmann, P. Runge, Oxidation der Formazylverbindungen II, Ber. Deutsch. Chem. Ges. 27 (1894) 2920.
  • 2. GH. Findlay, The value of some tetrazolium salts as histochemical reagents for sulphydryl groups, J. Histochem. Cytochem. 3 (1955) 331.
  • 3. E. Koren, R. Kohen, I. Gınsburg, A CobaltBased Tetrazolium Salts Reduction Test to Assay Polyphenols J. Agric. Food Chem., 57 (2009) 7644.
  • 4. E. Seidler, The tetrazolium- Formazan System, Prog. in Histochem. and Cytochem. 24 (1991) 1.
  • 5. R. Kuhn, D. Jerchel, Reduktion von Tetrazoliumsalzen durch Bakterier garende Hefe und keimende Samen., Ber. Deutsch. Chem. Ges. 74 (1941) 949.
  • 6. AN Babu, RR. Nadendla, Synthesis of some new quinazolinone formazans as anti-Inflammatory and anthelmintic agents, J. of Pharm. Res. 4 (2011) 983.
  • 7. W. Reid, Formazane und Tetrazoliumsalze, ihre Synthesen und ihre Bedeutung als Reduktionsindikatoren und Vitalfarbstoffe, Angew. Chem. 64 (1951) 391.
  • 8. JA. Plumb, R. Milroy, SB. Kaye, Effects of the pH Dependence of 3-(4,5- Dimethylthiazol-2-yl)-2,5- diphenyltetrazoliumBromide-Formazan, Cancer Res 49 (1989) 4435.
  • 9. H. Tezcan, N. Özkan, Substituent effects on the spectral properties of some 3-substituted Formazans, Dyes and Pigments 56 (2003) 159.
  • 10. H. Wan, R. Williams, P. Doherty, DF. Williams, The cyctotoxicity evaluation of Kevlar and Silicon Carbide by MMT assay, J. Mat. Sci. Mat. Med. 5 (1994) 154.
  • 11. FP. Altman, Tetrazolium salts and formazans. Prog. Histochem. Cytochem. 9 (1976) 1.
  • 12. J P. Raval, PR. Patel, NH. Patel, PS. Patel, Synthesis, Characeterization and in vitro antibacterial activity of novel 3-(4-methoxyphenyl)-1-isonicotinoyl5-(substituted phenyl)-formazans, Inter. J. of ChemTech Res. 1, No.3 (2009) 610.
  • 13. JP. Raval, PR. Patel, PS. Patel, In vitro Antitubercular activity of novel 3-(4- Methoxyphenyl)-1- isonicotinoyl-5-(substituted phenyl)-formazans, Inter. J. of ChemTech Res. 1 No.4 1548.
  • 14. S. Hunig, O. Boes, Beitrage zur substituentenwirkung, Liebigs Ann. Chem. 28 (1953) 579.
  • 15. AW. Nineham, The Chemistry of Formazans and Tetrazolium Salts, Chem. Rev. 55 (1955) 355.
  • 16. H. Tezcan, ML. Aksu, Electrochemical properties of 1-(o,m,p-nitrophenyl)-3- (m−nitro phenyl)-5- phenylformazans and their nickel complexes, Turk J Chem 34 (2010) 465.
  • 17. FR. Besson, W. Hartzell, WL. Savell, 1-(3,4-Dimethylphenyl)-5-methyltetrazole, J. Am. Chem. Soc. 73 (1951) 4457.
  • 18. L. Hunter, CB. Roberts, Associating effect of the hydrogen atom. IX. The N-H bond. Virtual tautomerism of the formazyl compounds, J. Chem. Soc. (1941) 820.
  • 19. I. Hausser, D. Jerchel, R. Kuhn, The red-yellow rearrangement of formazans by light Chem. Ber. 82 (1949) 515.
  • 20. GI. Sigeikin, GN. Lipunova, IG.Pervova, Formazans and their metal complexes, Russ. Chem. Rev. 75 (2006) 885.
  • 21. G. Buemi, F. Zuccarello, P. Venuvanalingam, M. Ramalingam, SS. Ammal, Ab initio study of formazan and 3-nitroformazan, J. Chem. Soc., Faraday Trans. 94 (1998) 3313.
  • 22. H. Tezcan, E. Uzluk, The synthesis and spectral properties determination of 1,3-substituted phenyl5-phenylformazans, Dyes and Pigments 75 (2007) 633.
  • 23. NA. Frolova, SZ. Vatsadze, NY. Vetokhina, VE. Zavodnik, NV. Zyk, New C-arylation reaction found during a study on the interaction of aldo hydrazones and arenediazonium chlorides, Mendeleev Commun., 16 (2006) 251.
  • 24. KG. Desai, KR. Desai, Microbial screening of novel synthesized formazans having amide linkages, J. of Heterocyc. Chem. 43 (2006) 1083.
  • 25. G. Mariappan, R. Korim et al, Synthesis and biological evaluation of formazan derivatives, J. Adv. Pharm. Tecn.& Res. 1 (2010) 396.
  • 26. VZ. Mady, I. Pinter, MP. Kajtar, A. Perczel, Transformation of aldose formazans, Novel synthesis of 2-acetamido-2-deoxypentonolactones and a new pent-2-enose formazan, Carbohydrate Research 346 (2011) 1534.
  • 27. H. Tezcan, Synthesis and spectral properties of some bis-substituted formazans, Spectrochim. Acta Part A 69 (2008) 971.
  • 28. YA. Ibrahim, AHM. Elwahy, AA. Abbas, New synthesis of macrocyclic crown-formazans from pyruvic acid derivatives, Tetrahedron 50 39 (1994) 11489.
  • 29. M. Ishiyama, M. Shiga, et al., A new sulfonated tetrazolium salts, Chem. Pharm. Bull. 41 6 (1993) 1118.
  • 30. M. Ishiyama, Y. Miyazono, et al., A highly watersoluble disulfonated tetrazolium salts, Talanta 44 (1997) 1299.
  • 31. OE. Sherif, Effect of solvents on the electronic absorption spectra of some substituted diarylformazans, Monat. Für Chem 128 (1997) 981.
  • 32. JW. Lewis, C. Sandfory, Infrared absorption and resonance Raman scattering of Photochromic triphenylformazans, J. Chem. 61 (1983) 809.
  • 33. AA. Abbas and AHM. Elwahy, Synthesis of spirolinked macrocyclic crown formazans and a bis(crown formazan), Arkivoc x (2009) 65.
There are 33 citations in total.

Details

Primary Language English
Authors

Hülya Şenöz This is me

Publication Date August 1, 2012
IZ https://izlik.org/JA73HA24BD
Published in Issue Year 2012 Volume: 40 Issue: 3

Cite

APA Şenöz, H. (2012). The Chemistry of Formazans and Tetrazolium Salts. Hacettepe Journal of Biology and Chemistry, 40(3), 293-301. https://izlik.org/JA73HA24BD
AMA 1.Şenöz H. The Chemistry of Formazans and Tetrazolium Salts. HJBC. 2012;40(3):293-301. https://izlik.org/JA73HA24BD
Chicago Şenöz, Hülya. 2012. “The Chemistry of Formazans and Tetrazolium Salts”. Hacettepe Journal of Biology and Chemistry 40 (3): 293-301. https://izlik.org/JA73HA24BD.
EndNote Şenöz H (August 1, 2012) The Chemistry of Formazans and Tetrazolium Salts. Hacettepe Journal of Biology and Chemistry 40 3 293–301.
IEEE [1]H. Şenöz, “The Chemistry of Formazans and Tetrazolium Salts”, HJBC, vol. 40, no. 3, pp. 293–301, Aug. 2012, [Online]. Available: https://izlik.org/JA73HA24BD
ISNAD Şenöz, Hülya. “The Chemistry of Formazans and Tetrazolium Salts”. Hacettepe Journal of Biology and Chemistry 40/3 (August 1, 2012): 293-301. https://izlik.org/JA73HA24BD.
JAMA 1.Şenöz H. The Chemistry of Formazans and Tetrazolium Salts. HJBC. 2012;40:293–301.
MLA Şenöz, Hülya. “The Chemistry of Formazans and Tetrazolium Salts”. Hacettepe Journal of Biology and Chemistry, vol. 40, no. 3, Aug. 2012, pp. 293-01, https://izlik.org/JA73HA24BD.
Vancouver 1.Hülya Şenöz. The Chemistry of Formazans and Tetrazolium Salts. HJBC [Internet]. 2012 Aug. 1;40(3):293-301. Available from: https://izlik.org/JA73HA24BD

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