The Chemistry of Formazans and Tetrazolium Salts

Year 2012, Volume: 40 Issue: 3, 293 - 301, 01.08.2012

Hülya Şenöz

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.

Keywords

Formazan, Tetrazolium salts, Tautomerization, Chelate form

Formazanlar ve Tetrazolyum Tuzlarının Kimyası

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

Keywords

Formazan, tetrazolyum tuzları, tautomeri, şelat yapı

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.