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Licensed Unlicensed Requires Authentication Published by De Gruyter March 31, 2013

Biologically Active Tin Compounds Based on Aziridine and Azepane Derivatives

Biologisch aktive Zinnverbindungen basierend auf Aziridin- und Azepan-Derivaten
H. El-Sharkawy Ali

Abstract

Four of new tin(IV) compounds derived from aziridine and azepane substituents have been synthesized and characterization by elemental microanalysis, atomic absorption, FT-IR and 1H-NMR spectroscopy. These tin-derived compounds exhibited biocidal activities on four different microorganisms: Escherichia coli, Staphylococcus aureus, Candida albicans and Aspergillus niger. The use of common and effective biocides depends on the surfactant molecules. On this basis, surface tension measurements were used to determine the critical micellar concentration (cmc), the minimum average area per surfactant molecule (Amin) and the surface excess concentration (Γ). A direct relationship has found between the antimicrobial efficacy and Γ.

Kurzfassung

Vier von neuen Zinn(IV)-Verbindungen, derivatisiert aus Aziridin- und Azepan-Substituenten, wurden synthetisiert und mittels elementarer Mikroanalyse, Atomabsorption, FT-IR- und 1H-NMR-Spekroskopie charakterisiert. Diese zinnderivatisierten Verbindungen zeigen eine biozide Aktivität auf vier verschiedene Mikroorganismen: Escherichia coli, Staphylococcus aureus, Candida albicans und Aspergillus niger. Die allgemeine Anwendung und Biozideffektivität ist abhängig von den Tensidmolekülen. Aufgrund dessen wurden Messungen von Oberflächenspannungen genutzt, um die kritische Mizellbildungskonzentration (cmc), die Minimumdurchschnittsfläche pro Tensidmolekül (Amin) und die Oberflächenüberschusskonzentration (Γ) zu bestimmen. Dabei wurde ein direkter Zusammenhang zwischen der antimikrobiellen Wirksamkeit und Γ gefunden.


Hanan El-Sharkawy Ali, Petrochemicals Department, Egyptian Petroleum Research Institute (EPRT), Nasr City, Cairo, Egypt. E-mail:

Hanan El-Sharkawy Ali Ahmed is a doctor in the Surfactant Laboratory, Petrochemicals Department, Egyptian Petroleum Research Institute (EPRI). She earned her Ph.D. in Organic Chemistry in 2003, and her M.Sc. in Organic Chemistry in 1999, both from the College of Women, Ain Shams University, Cairo, Egypt. Her experience includes working as an instructor in the field of instrumental analysis, surfactants, petrochemicals and advanced organic chemistry; bioremediation and waste water; bioremediation and crude oil; microorganisms and environmental effects; metal complexes, antimicrobial activity and anti-tumors; chemical reactions and synthesis (PTC/OH); surfactants and surface tension measurements; and instrumental analysis with UV & IR.


References

1.Robert, G.: Franzén Recent Advances in the Preparation of Heterocycles on Solid Support. J Comb Chem2 (3) (2000)195214. 10.1021/cc000002fSearch in Google Scholar

2.Vyas, R., Gao, G. Y., Harden, J. D. and Zhang, X. P.: Org Lett6(2004)1907. 10.1021/ol049691kSearch in Google Scholar

3.Yuhong, J., Rajender, S. and Varma, S. R.: Aqueous N-Heterocyclization of Primary Amines and Hydrazines with Dihalides: Microwave-Assisted Syntheses of N-Azacycloalkanes, Isoindole, Pyrazole, Pyrazolidine, and Phthalazine Derivatives. J Org Chem71(2006)135.10.1021/jo051878hSearch in Google Scholar

4.Chen, Y., Fields, K. B. and Zhang, X. P.: J Am Chem Soc126(2004)14178.10.1021/ja044889lSearch in Google Scholar

5.Lee, S. J. and Beak, P.: Asymmetric Synthesis of 4, 5, 6- and 3, 4, 5, 6-Substituted Azepanes by a Highly Diastereoselective and Enantioselective Lithiation-Conjugate Addition Sequence. J AM CHEM SOC. 128(2006)21782179. 10.1021/ja057592bSearch in Google Scholar

6.Samuelsson, J. and Johansson, M.: J Am Oil Chem Soc78(2001)11911196. 10.1007/s11745-001-0412-ySearch in Google Scholar

7.Chauvière, G., Bouteille, B., Enanga, B., de Albuquerque, C., Croft, S. L., Dumas, M. and Périé, J.: Synthesis and Biological Activity of Nitro Heterocycles Analogous to Megazol, a Trypanocidal Lead. J Med Chem46(2003)427440.Search in Google Scholar

8.Loupy, A. and Perreux, A.: Tetrahedron57(2001)9199. 10.1016/S0040-4020(01)00905-XSearch in Google Scholar

9.Rinner, U., Heather, L., Hillebrenner, H. L., Adams, D. R., Hudlicky, T., George, R. and Pettit, G. R.: Synthesis and biological activity of some structural modifications of pancratistatin. Bioorganic & Medicinal Chemistry Letters14(2004)29112915. 10.1016/j.bmcl.2004.03.032Search in Google Scholar PubMed

10.Jachuck, R. J. J., Selvaraj, D. K. and Varma, R. S.: Green Chem(2006)8.10.1039/B512732GSearch in Google Scholar

11.Fürmeier, S. and Metzger, J. O.: Fat-Derived Aziridines and Their N-Substituted Derivatives: Biologically Active Compounds Based on Renewable Raw Materials. Eur J Org Chem(2003)649659.Search in Google Scholar

12.Musluoglua, E. and Ahsen, V.: Synthesis and Characterization of 1,2-Bis(aziridin-N-yl)glyoxime and its Nickel(II), Palladium(II) and Cobalt(II) Complexes. J Chem Research (S)(1999)142143. 10.1039/a807944gSearch in Google Scholar

13.Gao, G.-Y., Harden, J. D. and Zhang, X. Z.: Cobalt-Catalyzed Efficient Aziridination of Alkenes. Amer Chem Soc7 (15) (2005)31913193. 10.1021/ja0439625Search in Google Scholar

14.Liang, J. L., Huang, J. S., Yu, X. Q., Zhu, N. and Che, C. M.: Chem Eur J8(2002)1563. 10.1002/1521-3765(20020402)8:7<1563::AID-CHEM1563>3.0.CO;2-VSearch in Google Scholar

15.Chen, Y. and Zhang, X. P.: J Org Chem69(2004)2431. 10.1021/jo049870fSearch in Google Scholar

16.Ali, H. E.-S.: Cycloalkylation reactions of fatty amines with α,ω-dihaloalkanes: Role of bis-quaternary ammonium salts as phase-transfer catalysts. Catalysis Communications8(2007)855860.Search in Google Scholar

17.Jain, M., Singh, V. and Singh, R. V.: Journal of the Iranian Chemical Society1(1)(2004)2027. 10.1007/BF03245766Search in Google Scholar

18.Sowa, F. J., Kenney, E. J. and Kenny, S.: United States Patent Office2(1952)470580.Search in Google Scholar

19.Zhu, S., Cheng, F., Wang, J. and Yu, J. G.: Anionic Gemini surfactants: Synthesis and aggregation properties in aqueous solutions. Colloids Surf A: Physicochem Eng Asp281(2006)3539.Search in Google Scholar

20.Ronconi, L., Marzano, C., Russo, U., Sitran, S., Graziani, R. and Fregona, D.: Appl Organometal Chem17(2003)916. 10.1002/aoc.389Search in Google Scholar

21.Shahzadi, S., Shahid, K., Ali, S., Mazhar, M. and Khan, K. M.: (2005) Journal of the Iranian Chemical Society2(4)(2005)277288. 10.1007/BF03245931Search in Google Scholar

22.Jonsson, B., Lindman, B., Holmbeug, K. and Kronberg, B.: (1998) Surfactants and Polymers in Aqueous Solution. Wiley, New York92(1998)3359.Search in Google Scholar

23.Bowers, J., Amos, K. E. and Bruce, D. W.: Surface and Aggregation Behavior of Aqueous solutions of Ru (II) Metallosurfactant, ISIS Facility, CLRC Rutherford Appleton Laboratory, Chilton, Didcot, Oxon, (2003).Search in Google Scholar

24.Mahmood, S., Ali, S., Bhatti, M. H., Mazhar, M. and Iqbal, R.: Synthesis, Characterization and Biological Applications of organotin(IV) Derivatives of 2-(2-Fluoro-4-biphenyl) propanoic Acid. Turk J Chem. 27(2003)657666.Search in Google Scholar

25.Benetollo, F., Lobbia, G. G., Mancini, M., Pellei, M. and Santini, C.: Journal of Organometallic Chemistry690(2005)19942001. 10.1016/j.jorganchem.2004.11.034Search in Google Scholar

26.Ouarzane, A. M., Franetich, J. F., Mazier, D., Pettit, G. R., Meijer, L., Doerig, C. and Desportes, L. I.: (2001) Antimicrob Agents Chemother45(2001)3409. 10.1128/AAC.45.12.3409-3415.2001Search in Google Scholar

27.Sharma, K. S., Hassan, P. A. and Rakshit, A. K.: Self aggregation of binary surfactant mixtures of a cationic dimeric (gemini) surfactant with nonionic surfactants in aqueous medium. Colloids Surf A: Physicochem Eng Asp 04.004 COLSUA-13794 (2006).Search in Google Scholar

28.Zhu, S., Cheng, F., Wang, J. and Yu, J. G.: Anionic Gemini surfactants: Synthesis and aggregation properties in aqueous solutions Colloids Surf A: Physicochem Eng Asp281(2006)3539.Search in Google Scholar

29.Jain, M., Gaur, S., Singh, V. P. and Singh, R. V.: Appl Organomet Chem18(2004)73. 10.1002/aoc.573Search in Google Scholar

30.Sexena, C. and Singh, R. V.: Phosphorus Sulfur Silicon97(1994)17. 10.1080/10426509408020723Search in Google Scholar

Received: 2007-10-30
Published Online: 2013-03-31
Published in Print: 2008-03-01

© 2008, Carl Hanser Publisher, Munich

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