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Synthesis of Novel Fluorescent Cyclohexenone Derivatives and their Partitioning Study in Ionic Micellar Media

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Abstract

An approach is demonstrated toward the synthesis of four novel cyclohexenone derivatives (CDs) via a convenient route of Michael addition of ethyl acetoacetate. The molecular structures of CDs were confirmed by means of FT-IR, 1H NMR, EIMS, UV and also by X-ray single crystal structure analysis. CDs are strongly fluorescent compounds and their fluorescent spectra exhibits intense violet fluorescence. To model the binding to biological membranes the behavior of CDs in micellar solutions of a cationic surfactant, cetyltrimethylammonium bromide (CTAB) and an anionic surfactant, sodium dodecylsulfate (SDS) has also been examined. The characteristics of partition and binding interactions of CDs with CTAB and SDS were investigated by UV-Visible and fluorescence spectroscopic techniques. Higher values of all mentioned interactions in case of CTAB, compared to SDS, indicate that there are greater interactions between the CDs and CTAB than with SDS.

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References

  1. Mohr A, Talbiersky P, Korth HG, Sustmann R, Boese R, Blalser D, Rehage H (2007) A new pyrene-based fluorescent probe for the determination of critical micelle concentrations. J Phys Chem B 111:12985–12992

    Article  CAS  PubMed  Google Scholar 

  2. Hirano J, Hamase K, Akita T, Zaitsu K (2008) Structural and photophysical properties of novel dual fluorescent compounds, 1-aryl-substituted 6-methoxy-4-quinolones. Luminescence 23:350–355

    Article  CAS  PubMed  Google Scholar 

  3. Hayakawa K, Ohsuki S, Kanematsu K (1986) General approach for the stereocontrolled synthesis of tricyclic lactones via allene intramolecular cycloaddition. An application to the synthesis of (±)-platyphyllide. Tetrahedron Lett 27:947–950

    Article  CAS  Google Scholar 

  4. Mori K, Kato M (1986) Synthesis and absolute configuration of (+)-hernandulcin. A new sesquiterpene with intensely sweet taste. Tetrahedron Lett 27:981–982

    Article  CAS  Google Scholar 

  5. Zhi L, Martinborought E (2001) Selective androgen receptor modulators (SARMs). Ann Rep Med Chem 36:169–180

    Article  CAS  Google Scholar 

  6. Bringmann G, Lang G, Muhlbacher J, Schaumann K, Steffens S, Rytik PG, Hentschel U (2003) Sorbicillactone A, a structurally unprecedented bioactive novel-type alkaloid from a sponge-derived fungus. Marine Mol Biotech 1:231–253

    Google Scholar 

  7. Bringmann G, Lang G, Muhlbacher J, Schaumann K, Steffens S, Muller WEG (2002) Method for producing sorbicillactone A. German Patent Application. (DE. 102 38 257.3)

  8. Kong C, Xu X, Zhou B, Hu F, Zhang C, Zhang M (2004) Two compounds from allelopathic rice accession and their inhibitory activity on weeds and fungal pathogens. Phytochem 65:1123–1128

    Article  CAS  Google Scholar 

  9. Stang PJ, Treptow WL (1981) Synthesis and biological activity of simple vinyl and methylene butyrolactone sulfonate esters and silyl enol ethers. J Med Chem 24:468–472

    Article  CAS  PubMed  Google Scholar 

  10. Li JY, Strobel GA (2001) Jesterone and hydroxy-jesterone antioomycetcyclohexenenone epoxides from the endophytic fungus. Phytochem 57:261–265

    Article  CAS  Google Scholar 

  11. Nagarajan K, David J, Shah RK (1976) Central nervous system active 5-oxo-1, 4, 5, 6, 7, 8-hexahydrocinnolines. J Med Chem 19:508–511

    Article  CAS  PubMed  Google Scholar 

  12. Eddington ND, Cox DS, Roberts RR, Stables JP, Powell CB, Scott AR (2000) Enaminones-versatile therapeutic pharmacophores. Further advances. Curr Med Chem 7:417–436

    CAS  PubMed  Google Scholar 

  13. Kachhadia VV, Popat KH, Nimavat KS, Joshi HS (2004) Synthesis, antitubercular and antimicrobial activity of 6-carbethoxy-5-aryl-3-[p-(3′-chloro-2′-benzo [b]thiophenoylamino)phenyl]-2-cyclohexenones. J Indian Chem Soc 81:694–695

    CAS  Google Scholar 

  14. Luu B, Aguilar JLGD, Junges CG (2000) Cyclohexenonic long-chain fatty alcohols as neuronal growth stimulators. Molecules 5:1439–1460

    Article  CAS  Google Scholar 

  15. House HO (1972) Modern synthetic reactions. Benjamin WA, Menlo Park

    Google Scholar 

  16. Jung ME (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis. Pergamon, Oxford

    Google Scholar 

  17. Reddy DB, Reddy AS, Padmavathi V (1998) Synthesis of annelated 1,2,3-selena- or -thia-diazoles. J Chem Research (S) 784–785

  18. Padmavathi V, Sharmila K, Reddy AS, Reddy DB (2001) Synthesis of spirocyclohexanones. Indian J Chem Sect B 40:11–14

    Google Scholar 

  19. Padmavathi V, Sharmila K, Padmaja A, Reddy DB (1999) An efficient synthesis of 6, 8-diarylcarbazoles via Fischer indole cyclizations. Heterocycl Commun 5:451–456

    CAS  Google Scholar 

  20. Padmavathi V, Reddy BJM, Balaiah A, Venugopal K, Reddy DB (2000) Synthesis of some fused pyrazoles and isoxazoles. Molecules 5:1281–1286

    Article  CAS  Google Scholar 

  21. Padmavathi V, Sharmila K, Balaiah A, Reddy AS, Reddy DB (2001) Cyclohexenone carboxylates. A versatile source for fused isoxazoles and pyrazoles. Synth Commun 31:2119–2126

    Article  CAS  Google Scholar 

  22. Usova EB, Lysenko LI, Krapivin GD, Kulnevich VG (1997) Furylcyclohexenones. Conversion of 6-ethoxycarbonylcyclohexenones into 4, 5-dihydroindazoles. Molecular and crystal structure of 4-phenyl-6-(5-methyl-2-furyl)-4, 5-dihydroindazol-3-one. Chem Heterocycl Compd 33:1259–1265

    Article  CAS  Google Scholar 

  23. Sreevidya TV, Narayana B, Yathirajan HS (2010) Synthesis and characterization of some chalcones and their cyclohexenone derivatives. Cent Eur J Chem 8:174–181

    Article  CAS  Google Scholar 

  24. Porzelle A, Williams CM, Schwartz BD, Gentle IR (2005) Evaluating the Baylis-Hillman reaction of cyclic enones using surfactants in water. Synlett 19:2923–2926

    Google Scholar 

  25. Zhu L, Ruan X, Chen B, Zhu R (2008) Efficient removal and mechanisms of water soluble aromatic contaminants by a reduced-charge bentonite modified with benzyltrimethyl-ammonium cation. Chemosphere 70:1987–1994

    Article  CAS  PubMed  Google Scholar 

  26. Rodrigues C, Gameiro P, Reis S, Lima J, de Castro B (2002) Interaction of grepafloxacin with large unilamellar liposomes: partition and fluorescence studies reveal the importance of charge interactions. Langmuir 18:10231–10236

    Article  CAS  Google Scholar 

  27. Schreier S, Malheiros SVP, de Paula E (2000) Surface active drugs: self-association and interaction with membranes and surfactants, Physicochemical and biological aspects. Biochim Biophys Acta 1508:210–234

    Article  CAS  PubMed  Google Scholar 

  28. Kim EJ, Shah DO (2002) Cloud point phenomenon in amphiphilic drug solutions. Langmuir 18:10105–10108

    Article  CAS  Google Scholar 

  29. Badshah A, Hasan A, Barbarie CR, Abbas A, Ali S (2009) Ethyl 6-(4-ethoxyphenyl)-4-(furan-2-yl)-2-oxocyclohex-3-ene-1-carboxylate. Acta Cryst E65, o70. doi:10.1107/S1600536808040130

  30. Miyashita Y, Hayano S (1981) Kinetic study of the penetration of an anthraquinoid acidic dye into cationic micelles. Bull Chem Soc Jpn 54:3249–3252

    Article  CAS  Google Scholar 

  31. Wang L, Verrall RE (1994) Apparent molar volume and apparent molar adiabatic compressibility studies of anesthetic molecules in aqueous micelle solutions of CTAB and CTAC as a function of surfactant concentration and temperature. J Phy Chem 98:4368–4374

    Article  CAS  Google Scholar 

  32. Khamis M, Bulos B (2005) Azo dyes interactions with surfactants, Determination of the critical micelle concentration from acid-base equilibrium. Dyes Pigments 66:179–183

    Article  CAS  Google Scholar 

  33. Khan AM, Shah SS (2008) A UV-visible study of partitioning of pyrene in an anionic surfactant sodium dodecyl sulfate. J Disp Sci Technol 29:1401–1407

    Article  CAS  Google Scholar 

  34. Bahri MA, Hoebeke M, Grammenos A, Delanaye L, Vandewalle N, Seret A (2006) Investigation of SDS, DTAB and CTAB micelle microviscosities by electron spin resonance. Colloids Surf A 290:206–212

    Article  CAS  Google Scholar 

  35. Rosen MJ (2004) Surfactants and interfacial phenomena. Wiley, New Jersey

    Book  Google Scholar 

  36. Elworthy PH, Florence AT, Macfarlane CB (1968) Solubilization by surface-active agent. Champman and Hall, London

    Google Scholar 

  37. Kawamura H, Manabe M, Miyamoto Y, Fujita Y, Tokunaga S (1989) Partition coefficients of homologous phenylalkanols between water and sodium dodecyl sulfate micelles. J Phys Chem 93:5536–5540

    Article  CAS  Google Scholar 

  38. Nazar MF, Khan AM, Shah SS (2009) Microemulsion system with improved loading of piroxicam: A study of microstructure, AAPS Pharm. Sci Tech In press. doi:10.1208/s12249-009-9328-9

  39. Kang J, Liu Y, Xie MX, Li S, Jiang M, Wang YD (2004) Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim Biophys Acta 1674:205–214

    CAS  PubMed  Google Scholar 

  40. Khan SN, Islam B, Rajeswari MR, Usmani H, Khan AU (2008) Interaction of anesthetic supplement thiopental with human serum albumin. Acta Biochim Pol 55:399–409

    CAS  PubMed  Google Scholar 

  41. Ahmad B, Parveen S, Khan RH (2006) Effect of albumin conformation on the binding of ciprofloxacin to human serum albumin: a novel approach directly assigning binding site. Biomacromolecules 7:1350–1356

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

Authors express gratitude the Quaid-i-Azam University for provision of lab facility and gratefully acknowledge the Higher Education Commission of Pakistan for sponsorship.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, 45320, Islamabad, Pakistan

    Amir Badshah, Saleem Nawaz, Muhammad Faizan Nazar, Syed Sakhawat Shah & Aurangzeb Hasan

  2. School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK

    Muhammad Faizan Nazar

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  1. Amir Badshah
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  2. Saleem Nawaz
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  3. Muhammad Faizan Nazar
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  4. Syed Sakhawat Shah
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  5. Aurangzeb Hasan
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Correspondence to Muhammad Faizan Nazar.

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Badshah, A., Nawaz, S., Nazar, M.F. et al. Synthesis of Novel Fluorescent Cyclohexenone Derivatives and their Partitioning Study in Ionic Micellar Media. J Fluoresc 20, 1049–1059 (2010). https://doi.org/10.1007/s10895-010-0657-6

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  • DOI: https://doi.org/10.1007/s10895-010-0657-6

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