Andriyashin Vitalij Vladimirovich

Bakhtiyarova Yuliya Valerevna

Cherkasov Rafael Ashatovich

Galkin Vladimir Ivanovich

Galkina Irina Vasilevna

Kazan Federal University Digital Repository

This article was downloaded by: [Moskow State Univ Bibliote]On: 05 November 2013, At: 03:16Publisher: Taylor & FrancisInforma Ltd Registered in England and Wales Registered Number: 1072954 Registeredoffice: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UKPhosphorus, Sulfur, and Silicon and theRelated ElementsPublication details, including instructions for authors andsubscription information:http://www.tandfonline.com/loi/gpss20Synthesis and Antimicrobial Activitiesof Phosphonium Salts on Basis ofTriphenylphosphine and 3,5-Di-Tert-Butyl-4-Hydroxybenzyl BromideIrina Galkina a , Yuliya Bakhtiyarova a , Vitaliy Andriyashin a ,Vladimir Galkin a & Rafael Cherkasov aa A. M. Butlerov Chemical Institute, Kazan Federal University ,Kazan , Tatarstan , Russian FederationAccepted author version posted online: 01 Nov 2012.Publishedonline: 08 May 2013.To cite this article: Irina Galkina , Yuliya Bakhtiyarova , Vitaliy Andriyashin , Vladimir Galkin &Rafael Cherkasov (2013) Synthesis and Antimicrobial Activities of Phosphonium Salts on Basis ofTriphenylphosphine and 3,5-Di-Tert-Butyl-4-Hydroxybenzyl Bromide, Phosphorus, Sulfur, and Siliconand the Related Elements, 188:1-3, 15-18, DOI: 10.1080/10426507.2012.740694To link to this article:  http://dx.doi.org/10.1080/10426507.2012.740694PLEASE SCROLL DOWN FOR ARTICLETaylor & Francis makes every effort to ensure the accuracy of all the information (the“Content”) contained in the publications on our platform. However, Taylor & Francis,our agents, and our licensors make no representations or warranties whatsoever as tothe accuracy, completeness, or suitability for any purpose of the Content. 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Terms &Conditions of access and use can be found at http://www.tandfonline.com/page/terms-and-conditionsDownloaded by [Moskow State Univ Bibliote] at 03:16 05 November 2013 Phosphorus, Sulfur, and Silicon, 188:15–18, 2013Copyright C© Taylor & Francis Group, LLCISSN: 1042-6507 print / 1563-5325 onlineDOI: 10.1080/10426507.2012.740694SYNTHESIS AND ANTIMICROBIAL ACTIVITIESOF PHOSPHONIUM SALTS ON BASISOF TRIPHENYLPHOSPHINEAND 3,5-DI-TERT-BUTYL-4-HYDROXYBENZYL BROMIDEIrina Galkina, Yuliya Bakhtiyarova, Vitaliy Andriyashin,Vladimir Galkin, and Rafael CherkasovA. M. Butlerov Chemical Institute, Kazan Federal University, Kazan, Tatarstan,Russian FederationGRAPHICAL ABSTRACTAbstract We report the structures of two new phosphonium salts prepared via the reactionof (substituted)benzyl bromides with triphenylphosphine. The antibacterial and antifungalactivities are reported.Keywords Phosphonium; antibacterial; antifungal; synthesis; X-ray structureRESULTS AND DISCUSSIONA new series of quaternary phosphonium salts 3–6 have been prepared by the reac-tion of triphenylphosphine with 3,5-di-tert-butyl-4-hydroxybenzyl bromide 2 in order toobtain novel compounds 5 and 6, soluble in water, for potential medical purposes. All thesynthesized compounds were screened for their antibacterial, antifungal activity (Table 1),and the target compounds 5 and 6 for their antioxidant activity (Table 2). The structure ofnew compounds was established from the IR, 1H, 31P-NMR spectra and from TG/DSC,XRD, and elemental analysis.Received 28 June 2012; accepted 14 October 2012.We are most grateful to Dr. Ziyatdinova G. K. for TAC determination.Address correspondence to Irina Galkina, A. M. Butlerov Chemical Institute, Kazan Federal University,Kremlevskaya 29/1, Kazan, Tatarstan 420008, Russian Federation. E-mail: gal.irina.2012@yandex.ru15Downloaded by [Moskow State Univ Bibliote] at 03:16 05 November 2013 16 I. GALKINA ET AL.Table 1 The in vitro antimicrobial activity of the synthesized salts and the control drugs (100 μg/0.1 mL)Microorganisms, zone of inhibition, (diameter, in mm)Staphylococcus Escherichia Pseudomonas Salmonella CandidaCompounds aureus сoli aeruginosa p .B albicans3 45 19 15 7 354 43 18 16 16 465 39 22 13.5 8 486 35 17 12 13 47Chlorhexidine 16 15 13 14 16.5Penicillin 23 16 8 10 —Griseofulvin — — — — 19Scheme 1 depicts the synthesis of different quaternary phosphonium salts (3–6) from2,6-di-tert-butyl-4-methylphenol (ionol) 1. Compound 2 was prepared from 1 accordingto reported method,1 which was then refluxed in diethyl ether with the solutions of corre-sponding phosphines to afford products 3, 4, 5, and 6. The obtained products were filtered,dried, and recrystallized. Both of phosphonium nitrates 5 and 6 were synthesized fromcorresponding phosphonium bromides 3 and 4 by reaction with AgNO3 in 2:1 EtOH:H2Osolution. The precipitate of AgBr was isolated; filtrate was concentrated in vacuum andgave the corresponding colorless products 5 and 6.The molecular structure of products 5 and 6 has been confirmed by X-ray analysis(Figures 1 and 2).The need of new antimicrobial and antioxidant drugs is justified because more mi-croorganisms are being resistance to the present drugs available on the market. Resistanceof pathogenic bacteria to antibiotics is rapidly becoming a major problem in the medicalcommunity and hospital-based healthcare settings. The search for novel agents to combatresistant bacteria has become one of the most important areas of antibacterial researchtoday.2The synthesized compounds 3, 4, 5, and 6 were screened for antibacterial and antifun-gal activity at 100 μg/0.1 mL concentrations by using the cup–plate agar diffusion method,Table 2 Total antioxidant capacity of quaternary phosphonium salts 5 and 6N Compounds TAC (kC mol−1) RSD (%)5 275 ± 5 1.66 237 ± 10 3.5Control 1 α-Tocopherol 195 ± 3 1.4Control 2 Ascorbic acid 185 ± 4 2.2Downloaded by [Moskow State Univ Bibliote] at 03:16 05 November 2013 SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF PHOSPHONIUM SALTS 17Scheme 1Figure 1 Structure of 5. (Color figure available online).and standard drugs used were chlorhexidine, penicillin, and griseofulvin. The novel synthe-sized phosphonium salts 3–6 show maximal activity against pathogenic microorganisms.Starting compounds 1 and 2 were not active at all. These results are reported in Table 1.Such a high biological activity of phosphonium bromides 3–6, we explain by theirability to be integrated into the lipid layers of biomembranes of pathogenic microfloraeventually leading to the destruction of this last. To confirm this idea, we studied the inter-action mechanism of phosphonium salts – synthetic phosphorus analogs of biomembranes –with natural biological membranes (lecithin) using the model of Langmuir monolayers. Itwas discovered that phosphonium salts interact with lecithin, by forming a pores, and thusdeteriorating the membrane functions.3Figure 2 Structure of 6. (Color figure available online).Downloaded by [Moskow State Univ Bibliote] at 03:16 05 November 2013 18 I. GALKINA ET AL.Determination of TAS (Total Antioxidant Activity) is based on the coulometrictitration of analyte by electrogenerated bromine. Bromine has been electrochemicallygenerated at a current density 5 mA cm−2 providing 100% current yield. The end-pointsin amperometric titration have been measured with two polarized platinum electrodes(E = 300 mV). TAC experiments have been carried out at ambient temperature23 ± 2◦C. These results are reported in Table 2.So, it may be concluded from our results that the synthesized compounds are potentantimicrobial agents against pathogenic bacteria and fungi.REFERENCES1. Starnes, W. H.; Lauff, J. J. J. Org. Chem. 1970, 35, 1978-1986.2. Aysel, G.; Taylan, I.; Nalan, T.; Gulten, O. Turkish J. Pharm. Sci. 2005, 2, 1-10.3. Galkina, I. V.; Melnikova, N. B.; Bakhtiyarova, Yu. V.; Stakheev, V. V.; Galkin, V. I.; Zhiltsova,O. Ye.; Zhukova, O. V.; Egorova, S. N. Pharmaciya (Russian J. Farmacy) 2010, 3, 47-49.Downloaded by [Moskow State Univ Bibliote] at 03:16 05 November 2013 

Synthesis ans antimicrobial activities of phosphonium salts on basis of triphenylphosphine and 3.5-ditert-butyl-4-hydroxybenzyl bromide

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Synthesis ans antimicrobial activities of phosphonium salts on basis of triphenylphosphine and 3.5-ditert-butyl-4-hydroxybenzyl bromide

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