Research Article
BibTex RIS Cite

Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of its charge transfer complexes

Year 2016, Volume: 20 Issue: 3, 425 - 431, 01.12.2016
https://doi.org/10.16984/saufenbilder.67697

Abstract

Monastrol which is a kinesin-5 inhibitor have been synthesized using 3-hydroxybenzaldehyde, thiourea and ethylasetoasetate in the presence of Alumina Sulphonic Acid (ASA) catalyst in solvent free system. Charge transfer complexes between monastrol as a donor and acceptors such as tetracyanoquinomethane (TCNQ) and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) have been studied spectrophotometrically in acetonitrile at 21 oC. The stoichiometry of the complexes was found to be 1:1 ratio by the Job method between donor and acceptors with the maximum absorption band at a wavelength of 742nm and 546nm respectively. The equilibrium constants were determined by Benesi-Hildebrand and thermodynamic parameters of the complexes by Van’t Hoff equation.

References

  • D.S. Bose, M. Sudharshan, S.W. Chavhan, “New protocol for Biginelli reaction-a practical synthesis of Monastrol,” Arkivoc, vol. 3, pp. 228-236, Feb. 2005.
  • C.O. Kappe, “Biologically active dihydropyrimidones of the Biginelli-type - a literature survey,” Eur.J.Med.Chem, vol. 35, no. 12, pp. 1043-1052, Dec. 2000.
  • R. Zheng, X. Wang, H. Xu, J. Du, “Bronsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones,” Synthetic Commun vol. 36, no. 11, pp. 1503-1513, Aug. 2006.
  • C.O. Kappe, “100 Years Of The Biginelli Dihydropyrimidine Synthesis,” Tetrahedron, vol. 49, no. 32, pp. 6937-6963, Aug. 1993.
  • C.O. Kappe, “Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog,” Accounts. Chem. Res. Vol. 33, no. 12, pp. 879-888, Apr. 2000.
  • D Russowsky, R.F.S. Canto, S.A.A. Sanches, M.G.M. D’Oca, A. de Fatima, R.A. Pilli, L.K. Kohn, M.A. Antonio, J.E. de Carvalho, “Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines: Monastrol, oxo-monastrol and oxygenated analogues,” Bioorg. Chem. vol. 34, no. 4, pp. 173-182, Aug. 2006.
  • E. Klein, S. DeBonis, B. Thiede, D.A. Skofias, F. Kozielski, L. Lebeau, “New chemical tools for investigating human mitotic kinesin Eg5,” Bioorg & Med. Chem. vol. 15, no. 19, pp. 6474-6488, Oct. 2007.
  • P. Taboada, M.G. Pichel, S. Barbosa, D. Attwood, V. Mosquera, “Effect of temperature on the volume and compressibilities of some amphiphilic penicillins in aqueous solution” Phys. Chem. Chem.Phys. vol. 5, no. 4, pp. 703-709. Apr. 2003
  • D.K. Roy, A. Saha, A.K. Mukherjee, “Spectroscopic and thermodynamic study of charge transfer complexes of cloxacillin sodium in aqueous ethanol medium”, Spectrochim. Acta A. vol. 61, no. 9, pp. 2017-2022, July 2005.
  • R.S. Mulliken, W.B. Pearson,”Molecular Complexes,” New York: Wiley Publishers, 1969, pp.16-48.
  • R. Foster, ”Charge Transfer Complexes,” London: Academic Press, 1969, pp. 25-50.
  • M.M.A. Hamed, M.I. Abdel-Hamid, M.R. Mahmoud, “Molecular complexes of some N-aryldithiocarbamates with pi-electron acceptors,” Monatshefte fur Chemie vol. 129, no. 2, pp. 121-127, Feb. 1998.
  • A. Dozal, H. Keyzer, H.K. Kim, W.W. Way, “Charge transfer complexes of K vitamins with several classes of antimicrobials”, Int. J. Antimic. Ag. vol. 14, no. 3, pp. 261-265, Apr. 2000.
  • E.H. El-Mossalamy, A.S. Amin, A.A. Khalil, “Charge transfer complexes of some oxazolones with iodine”, Spectrochim. Acta A. vol. 58, no. 1, pp. 67-72, Jan. 2002.
  • M. Arslan, H. Duymus, “Spectroscopic studies of charge transfer complexes between colchicine and some pi acceptors”, Spectrochim. Acta A. vol. 67, no. 3-4, pp. 573-577, July. 2007.
  • H. Duymus, M. Arslan, M. Kucukislamoglu, M. Zengin, “Charge transfer complex studies between some non-steroidal anti-inflammatory drugs and pi-electron acceptors”, Spectrochim. Acta A. Vol. 65, no. 5, pp. 1120-1124, Dec. 2006.
  • H. Demirhan, M. Arslan, M. Zengin, M. Kucukislamoglu, "Investigation of charge transfer complexes formed between mirtazapine and some pi acceptors," J. of Spectroscopy , 1- 7 , 2013. 10.1155/2013/875953
  • F.A.N. El-Dien, G.G. Mohamed, E.Y.Z.A. Farag, “Spectrophotometric determination of flucloxacillin and dicloxacillin in pure and dosage forms”, Spectrochim. Acta A. vol. 64, no. 1, pp. 210-215, May. 2006.
  • P. Kalimuthu, A. Sivanesan, S.A. John, “Charge-transfer interaction of aromatic thiols with 2,3-dichloro-5,6-dicyano-p-benzoquinone: Spectral and quantum mechanical studies,” J. Phys. Chem. A. vol. 111, no. 48, pp. 12086-12092, Dec. 2007.
  • M.S. Refat, H.A.D. Ahmed, L.A. El-Zayat, “Spectroscopic, synthesis and structural studies of piperidine-chloranilic acid and piperidine-picric acid charge transfer complexes,” Can. J. Anal. Sci. Spect. vol. 51, no. 3, pp. 147-163, Sep. 2006.
  • M.E. El-Zaria, A.R. Genady, “Spectroscopic studies of charge transfer complexes of meso-tetra-p-tolylporphyrin and its zinc complex with some aromatic nitro acceptors in different organic solvents,” Appl. Organomet. Chem. vol. 21, no. 11, pp. 983-993, Nov. 2007.
  • M. Wojdyla, B. Derkowska, Z. Lukasiak, W. Bala, “Absorption and photoreflectance spectroscopy of zinc plithalocyanine (ZnPc) thin films grown by thermal evaporation”, Mater. Lett. vol. 60, no. 29-30, pp. 3441-3446, Dec. 2006.
  • E.A. Taha, S.M. Soliman, H.E. Abdellatef, M.M. Ayad, “Colorimetric methods for the determination of some tricyclic antidepressant drugs in their pure and dosage forms,” Microchim. Acta vol. 140, no. 3-4, pp. 175-182, Oct. 2002.
  • S. Imre, M.T. Dogaru, C.E. Vari, T. Muntean, L. Kelemen, “Validation of an HPLC method for the determination of ciprofloxacin in human plasma,” J. Pharmaceut. Biomed. vol. 33, no. 1, pp.125-130, Sep. 2003.
  • F. Yakuphanoglu, M. Arslan, “Determination of thermo-optic coefficient, refractive index, optical dispersion and group velocity parameters of an organic thin film,” Physica B vol. 393, no. 1-2, pp. 304-309, Apr. 2007.
  • M. Arslan, F.B. Atak, F. Yakuphanoglu, “Synthesis and refractive index dispersion properties of the N,N ',N ''-trinaphthylmethyl melamine-DDQ complex thin film”, Opt. Mater. vol. 29, no. 5, pp. 516-520, Jan. 2007.
  • F. Yakuphanoglu, M. Arslan, “The fundamental absorption edge and optical constants of some charge transfer compounds,” Opt. Mater. vol. 27, no. 1, pp. 29-37, Oct. 2004.
  • S. Besoluk, M. Kucukislamoglu, M. Nebioglu, M. Zengin, M. Arslan, “Solvent-free synthesis of dihydropyrimidinones catalyzed by alumina sulfuric acid at room temperature”, J. Iran. Chem. Soc. vol. 5, no.1, pp. 62-66, Mar. 2008.
  • R. Job, Advenced Physicochemical Exp., London: Pitman, 1964, pp 12-26
  • H. A. Benesi, J.H. Hildebrand, “A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons,” J. Am. Chem. Soc. vol. 71, no. 8, pp. 2703-2707, Aug. 1949.
  • A.S. Amin, G.O. El-Sayed, Y.M. Issa, “Utility Of Certain Pi-Acceptors For The Spectrophotometric Determination Of Norfloxacin,” Analyst vol. 120, no. 4, pp. 1189-1193, Apr. 1995.
  • A.A.A. Boraei, “Spectroscopic study on charge transfer molecular complexes of pyrazole derivatives with some π-electron acceptors,” Spectrochim. Acta A vol. 58, no. 9, pp. 1895-1901, Jul. 2002.
  • E.H. El-mossalamy, “Molecular spectroscopic studies of charge transfer complexes of thiourea derivatives with benzoquinones,” J. Mol. Liq. vol. 123, no. 2-3, pp. 118-123, Jan. 2006.

Kinesin-5 inhibitörü olan Monastrol bileşiğinin sentezi ve yük transferi kompleks etkileşmelerinin incelenmesi

Year 2016, Volume: 20 Issue: 3, 425 - 431, 01.12.2016
https://doi.org/10.16984/saufenbilder.67697

Abstract

Kinesin-5 inhibitörü olarak kullanılan Monastrol, çözücüsüz ortamda alümina sülfonik asit (ASA) katalizörü varlığında 3-hidroksibenzaldehit, tiyoüre ve etilasetoasetat kullanılarak sentezlenmiştir. Elektron verici (Donör, D) olarak monastrol, elektron alıcı (Akseptör, A) olarak tetrasiyanoquinometan (TCNQ) kullanılmış ve bunlar ile 2,3-dikloro-5,6-disiyano-p-benzokinon (DDQ) bileşikleri arasındaki yük transfer kompleksleri asetonitril içinde 21 °C'de spektrofotometrik olarak incelenmiştir. Komplekslerin stokiyometrisi, Job yöntemi kullanılarak incelenmiş, elektron verici ve alıcılar arasında TCNQ ile 742 nm ve DDQ ile 546 nm dalga boyunda maksimum absorbsiyon bandında 1:1 oranında olduğu bulunmuştur. Komplekslerin denge sabiti Benesi-Hildebrand ve termodinamik parametreleri Van't Hoff denklemi ile belirlenmiştir.

References

  • D.S. Bose, M. Sudharshan, S.W. Chavhan, “New protocol for Biginelli reaction-a practical synthesis of Monastrol,” Arkivoc, vol. 3, pp. 228-236, Feb. 2005.
  • C.O. Kappe, “Biologically active dihydropyrimidones of the Biginelli-type - a literature survey,” Eur.J.Med.Chem, vol. 35, no. 12, pp. 1043-1052, Dec. 2000.
  • R. Zheng, X. Wang, H. Xu, J. Du, “Bronsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones,” Synthetic Commun vol. 36, no. 11, pp. 1503-1513, Aug. 2006.
  • C.O. Kappe, “100 Years Of The Biginelli Dihydropyrimidine Synthesis,” Tetrahedron, vol. 49, no. 32, pp. 6937-6963, Aug. 1993.
  • C.O. Kappe, “Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog,” Accounts. Chem. Res. Vol. 33, no. 12, pp. 879-888, Apr. 2000.
  • D Russowsky, R.F.S. Canto, S.A.A. Sanches, M.G.M. D’Oca, A. de Fatima, R.A. Pilli, L.K. Kohn, M.A. Antonio, J.E. de Carvalho, “Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines: Monastrol, oxo-monastrol and oxygenated analogues,” Bioorg. Chem. vol. 34, no. 4, pp. 173-182, Aug. 2006.
  • E. Klein, S. DeBonis, B. Thiede, D.A. Skofias, F. Kozielski, L. Lebeau, “New chemical tools for investigating human mitotic kinesin Eg5,” Bioorg & Med. Chem. vol. 15, no. 19, pp. 6474-6488, Oct. 2007.
  • P. Taboada, M.G. Pichel, S. Barbosa, D. Attwood, V. Mosquera, “Effect of temperature on the volume and compressibilities of some amphiphilic penicillins in aqueous solution” Phys. Chem. Chem.Phys. vol. 5, no. 4, pp. 703-709. Apr. 2003
  • D.K. Roy, A. Saha, A.K. Mukherjee, “Spectroscopic and thermodynamic study of charge transfer complexes of cloxacillin sodium in aqueous ethanol medium”, Spectrochim. Acta A. vol. 61, no. 9, pp. 2017-2022, July 2005.
  • R.S. Mulliken, W.B. Pearson,”Molecular Complexes,” New York: Wiley Publishers, 1969, pp.16-48.
  • R. Foster, ”Charge Transfer Complexes,” London: Academic Press, 1969, pp. 25-50.
  • M.M.A. Hamed, M.I. Abdel-Hamid, M.R. Mahmoud, “Molecular complexes of some N-aryldithiocarbamates with pi-electron acceptors,” Monatshefte fur Chemie vol. 129, no. 2, pp. 121-127, Feb. 1998.
  • A. Dozal, H. Keyzer, H.K. Kim, W.W. Way, “Charge transfer complexes of K vitamins with several classes of antimicrobials”, Int. J. Antimic. Ag. vol. 14, no. 3, pp. 261-265, Apr. 2000.
  • E.H. El-Mossalamy, A.S. Amin, A.A. Khalil, “Charge transfer complexes of some oxazolones with iodine”, Spectrochim. Acta A. vol. 58, no. 1, pp. 67-72, Jan. 2002.
  • M. Arslan, H. Duymus, “Spectroscopic studies of charge transfer complexes between colchicine and some pi acceptors”, Spectrochim. Acta A. vol. 67, no. 3-4, pp. 573-577, July. 2007.
  • H. Duymus, M. Arslan, M. Kucukislamoglu, M. Zengin, “Charge transfer complex studies between some non-steroidal anti-inflammatory drugs and pi-electron acceptors”, Spectrochim. Acta A. Vol. 65, no. 5, pp. 1120-1124, Dec. 2006.
  • H. Demirhan, M. Arslan, M. Zengin, M. Kucukislamoglu, "Investigation of charge transfer complexes formed between mirtazapine and some pi acceptors," J. of Spectroscopy , 1- 7 , 2013. 10.1155/2013/875953
  • F.A.N. El-Dien, G.G. Mohamed, E.Y.Z.A. Farag, “Spectrophotometric determination of flucloxacillin and dicloxacillin in pure and dosage forms”, Spectrochim. Acta A. vol. 64, no. 1, pp. 210-215, May. 2006.
  • P. Kalimuthu, A. Sivanesan, S.A. John, “Charge-transfer interaction of aromatic thiols with 2,3-dichloro-5,6-dicyano-p-benzoquinone: Spectral and quantum mechanical studies,” J. Phys. Chem. A. vol. 111, no. 48, pp. 12086-12092, Dec. 2007.
  • M.S. Refat, H.A.D. Ahmed, L.A. El-Zayat, “Spectroscopic, synthesis and structural studies of piperidine-chloranilic acid and piperidine-picric acid charge transfer complexes,” Can. J. Anal. Sci. Spect. vol. 51, no. 3, pp. 147-163, Sep. 2006.
  • M.E. El-Zaria, A.R. Genady, “Spectroscopic studies of charge transfer complexes of meso-tetra-p-tolylporphyrin and its zinc complex with some aromatic nitro acceptors in different organic solvents,” Appl. Organomet. Chem. vol. 21, no. 11, pp. 983-993, Nov. 2007.
  • M. Wojdyla, B. Derkowska, Z. Lukasiak, W. Bala, “Absorption and photoreflectance spectroscopy of zinc plithalocyanine (ZnPc) thin films grown by thermal evaporation”, Mater. Lett. vol. 60, no. 29-30, pp. 3441-3446, Dec. 2006.
  • E.A. Taha, S.M. Soliman, H.E. Abdellatef, M.M. Ayad, “Colorimetric methods for the determination of some tricyclic antidepressant drugs in their pure and dosage forms,” Microchim. Acta vol. 140, no. 3-4, pp. 175-182, Oct. 2002.
  • S. Imre, M.T. Dogaru, C.E. Vari, T. Muntean, L. Kelemen, “Validation of an HPLC method for the determination of ciprofloxacin in human plasma,” J. Pharmaceut. Biomed. vol. 33, no. 1, pp.125-130, Sep. 2003.
  • F. Yakuphanoglu, M. Arslan, “Determination of thermo-optic coefficient, refractive index, optical dispersion and group velocity parameters of an organic thin film,” Physica B vol. 393, no. 1-2, pp. 304-309, Apr. 2007.
  • M. Arslan, F.B. Atak, F. Yakuphanoglu, “Synthesis and refractive index dispersion properties of the N,N ',N ''-trinaphthylmethyl melamine-DDQ complex thin film”, Opt. Mater. vol. 29, no. 5, pp. 516-520, Jan. 2007.
  • F. Yakuphanoglu, M. Arslan, “The fundamental absorption edge and optical constants of some charge transfer compounds,” Opt. Mater. vol. 27, no. 1, pp. 29-37, Oct. 2004.
  • S. Besoluk, M. Kucukislamoglu, M. Nebioglu, M. Zengin, M. Arslan, “Solvent-free synthesis of dihydropyrimidinones catalyzed by alumina sulfuric acid at room temperature”, J. Iran. Chem. Soc. vol. 5, no.1, pp. 62-66, Mar. 2008.
  • R. Job, Advenced Physicochemical Exp., London: Pitman, 1964, pp 12-26
  • H. A. Benesi, J.H. Hildebrand, “A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons,” J. Am. Chem. Soc. vol. 71, no. 8, pp. 2703-2707, Aug. 1949.
  • A.S. Amin, G.O. El-Sayed, Y.M. Issa, “Utility Of Certain Pi-Acceptors For The Spectrophotometric Determination Of Norfloxacin,” Analyst vol. 120, no. 4, pp. 1189-1193, Apr. 1995.
  • A.A.A. Boraei, “Spectroscopic study on charge transfer molecular complexes of pyrazole derivatives with some π-electron acceptors,” Spectrochim. Acta A vol. 58, no. 9, pp. 1895-1901, Jul. 2002.
  • E.H. El-mossalamy, “Molecular spectroscopic studies of charge transfer complexes of thiourea derivatives with benzoquinones,” J. Mol. Liq. vol. 123, no. 2-3, pp. 118-123, Jan. 2006.
There are 33 citations in total.

Details

Subjects Engineering
Journal Section Research Articles
Authors

Mustafa Arslan

Nurcan Berber

Publication Date December 1, 2016
Submission Date April 13, 2016
Acceptance Date June 8, 2016
Published in Issue Year 2016 Volume: 20 Issue: 3

Cite

APA Arslan, M., & Berber, N. (2016). Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of its charge transfer complexes. Sakarya University Journal of Science, 20(3), 425-431. https://doi.org/10.16984/saufenbilder.67697
AMA Arslan M, Berber N. Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of its charge transfer complexes. SAUJS. November 2016;20(3):425-431. doi:10.16984/saufenbilder.67697
Chicago Arslan, Mustafa, and Nurcan Berber. “Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of Its Charge Transfer Complexes”. Sakarya University Journal of Science 20, no. 3 (November 2016): 425-31. https://doi.org/10.16984/saufenbilder.67697.
EndNote Arslan M, Berber N (November 1, 2016) Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of its charge transfer complexes. Sakarya University Journal of Science 20 3 425–431.
IEEE M. Arslan and N. Berber, “Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of its charge transfer complexes”, SAUJS, vol. 20, no. 3, pp. 425–431, 2016, doi: 10.16984/saufenbilder.67697.
ISNAD Arslan, Mustafa - Berber, Nurcan. “Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of Its Charge Transfer Complexes”. Sakarya University Journal of Science 20/3 (November 2016), 425-431. https://doi.org/10.16984/saufenbilder.67697.
JAMA Arslan M, Berber N. Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of its charge transfer complexes. SAUJS. 2016;20:425–431.
MLA Arslan, Mustafa and Nurcan Berber. “Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of Its Charge Transfer Complexes”. Sakarya University Journal of Science, vol. 20, no. 3, 2016, pp. 425-31, doi:10.16984/saufenbilder.67697.
Vancouver Arslan M, Berber N. Synthesis of Monastrol, Kinesin-5 inhibitör and ınvestigation of its charge transfer complexes. SAUJS. 2016;20(3):425-31.