Hülya ŞENÖZ

The chemistry of formazans and tetrazolium salts

Bu çalışmada tetrazolyum tuzları ve formazanların 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.

Formazanlar ve tetrazolyum tuzlarının kimyası

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 p-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.

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1. HV. Pechmann, P. Runge, Oxidation der Formazyl- verbindungen 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 Cobalt- Based 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 Reduktion- sindikatoren 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-isonicotinoyl- 5-(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-Di- methylphenyl)-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 phenyl- 5-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 water- soluble 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 spiro linked macrocyclic crown formazans and a bis(crown formazan), Arkivoc x (2009) 65.