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Impact of Inclusion Complex Formation on Absorption and Emission Characteristics of Some 4-Arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols
Corresponding Author(s) : Sunakar Panda
Asian Journal of Chemistry,
Vol. 28 No. 5 (2016): Vol 28 Issue 5
Abstract
The inclusion complexes of a series of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols have been synthesized with b-cyclodextrin. The compounds and their inclusion complexes have been characterized by studying their physical and spectral properties. The thermodynamic stability constant and free energy of activation have been determined to know the stability of inclusion complexes and type of host-guest relation. Finally, the absorption, excitation and emission spectra of the compounds and their inclusion complexes have been taken to examine whether the inclusion complex formation has any impact on absoption and emission characteristics of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols. It is found that inclusion complex formation brings about a drastic change in absorption, excitation and emission spectra of newly synthesized compounds.
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- R.M. Shaker, ARKIVOC, 59 (2006); doi:10.3998/ark.5550190.0007.904.
- H. Bayrak, A. Demirbas, S.A. Karaoglu and N. Demirbas, Eur. J. Med. Chem., 44, 1057 (2009); doi:10.1016/j.ejmech.2008.06.019.
- H. Bayrak, A. Demirbas, N. Demirbas and S.A. Karaoglu, Eur. J. Med. Chem., 44, 4362 (2009); doi:10.1016/j.ejmech.2009.05.022.
- J. Xu, Y. Cao, J. Zhang, S. Yu, Y. Zou, X. Chai, Q. Wu, D. Zhang, Y. Jiang and Q. Sun, Eur. J. Med. Chem., 46, 3142 (2011); doi:10.1016/j.ejmech.2011.02.042.
- O. Pintilie, L. Profire, V. Sunel, M. Popa and A. Pui, Molecules, 12, 103 (2007); doi:10.3390/12010103.
- B. Shivarama Holla, B. Veerendra, M.K. Shivananda and B. Poojary, Eur. J. Med. Chem., 38, 759 (2003); doi:10.1016/S0223-5234(03)00128-4.
- Y.A. Al-Soud, N.A. Al-Masoudi and A.R. Ferwanah, Bioorg. Med. Chem., 11, 1701 (2003); doi:10.1016/S0968-0896(03)00043-9.
- M.T. Abdel-Aal, W.A. El-Sayed, S.M. El-Kosy and E.S.H. El-Ashry, Arch. Pharm., 341, 307 (2008); doi:10.1002/ardp.200700154.
- L. Labanauskas, E. Udrenaite, P. Gaidelis and A. Brukstus, IL Farmaco, 59, 255 (2004); doi:10.1016/j.farmac.2003.11.002.
- L. Labanauskas, V. Kalcas, E. Uderenaite, P. Gaidelis, A. Brukstus and V. Dauksas, Pharmazie, 56, 617 (2001).
- S.A. Almasirad, M. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); doi:10.1016/j.bmcl.2004.09.072.
- B. Yang, J. Lin, Y. Chen and Y. Liu, Bioorg. Med. Chem., 17, 6311 (2009); doi:10.1016/j.bmc.2009.07.060.
- S. Panda and R. Sahu, Am. J. Adv. Drug Deliv., 1, 1 (2013).
- S. Panda and R. Sahu, J. Pharm. Bio. Sci., 9, 30 (2014).
- S. Panda and D.L. Singh, World J. Pharm. Pharm. Sci., 3, 1639 (2014).
- S. Panda, D.L. Singh and R. Sahu, Int. J. Chem. Pharm. Sci., 4, 1 (2013).
- A.A. Abdel-Shafi and S.S. Al-Shihry, Spectrochim. Acta A, 72, 533 (2009); doi:10.1016/j.saa.2008.10.052.
- I.V.M.V. Enoch and M.Swaminathan, J. Fluoresc., 14, 751 (2004); doi:10.1023/B:JOFL.0000047226.60559.09.
- R. Wang, L. Yuan and D.H. Macartney, Chem. Commun., 5867 (2005); doi:10.1039/b513246k.
- M. Maafi, B. Laassis, J.-J. Aaron, M.C. Mahedero, A.M. Peoa and F. Salinas, J. Inclus. Phenom. Mol. Recog.Chem., 22, 235 (1995); doi:10.1007/BF00707086.
- W. Misiuk, Indian J. Chem., 51A, 1706 (2012).
- R.M. Ahmed, M. Dani and A.A. Elbashir, Int. J. Pharm. Chem. Res., 2, 2278 (2013).
- G. Nelson, G. Patonay and I.M. Warner, Anal. Chem., 60, 274 (1988); doi:10.1021/ac00154a018.
- S. Panda, S. Nayak and P.K. Das, World J. Pharm. Pharm. Sci., 4, 939 (2015).
- T. Higuchi and K.A. Connors, Adv. Anal. Chem. Instrum., 4, 117 (1965).
- H. Ueda and T. Endo, Cyclodextrins and their Complexes, Chemistry, Analytical Methods, Applications, Wiley-VCH Verlag, Weinheim, pp. 370 (2006).
- H.A. Benesi and J.H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1999); doi:10.1021/ja01176a030.
- J. Szetli, Molecular Entrapment and Release Properties of Drugs By Cyclodextrins Controlled Drug Bioavailability, Wiley Interscience, pp. 365-420 (1985).
References
R.M. Shaker, ARKIVOC, 59 (2006); doi:10.3998/ark.5550190.0007.904.
H. Bayrak, A. Demirbas, S.A. Karaoglu and N. Demirbas, Eur. J. Med. Chem., 44, 1057 (2009); doi:10.1016/j.ejmech.2008.06.019.
H. Bayrak, A. Demirbas, N. Demirbas and S.A. Karaoglu, Eur. J. Med. Chem., 44, 4362 (2009); doi:10.1016/j.ejmech.2009.05.022.
J. Xu, Y. Cao, J. Zhang, S. Yu, Y. Zou, X. Chai, Q. Wu, D. Zhang, Y. Jiang and Q. Sun, Eur. J. Med. Chem., 46, 3142 (2011); doi:10.1016/j.ejmech.2011.02.042.
O. Pintilie, L. Profire, V. Sunel, M. Popa and A. Pui, Molecules, 12, 103 (2007); doi:10.3390/12010103.
B. Shivarama Holla, B. Veerendra, M.K. Shivananda and B. Poojary, Eur. J. Med. Chem., 38, 759 (2003); doi:10.1016/S0223-5234(03)00128-4.
Y.A. Al-Soud, N.A. Al-Masoudi and A.R. Ferwanah, Bioorg. Med. Chem., 11, 1701 (2003); doi:10.1016/S0968-0896(03)00043-9.
M.T. Abdel-Aal, W.A. El-Sayed, S.M. El-Kosy and E.S.H. El-Ashry, Arch. Pharm., 341, 307 (2008); doi:10.1002/ardp.200700154.
L. Labanauskas, E. Udrenaite, P. Gaidelis and A. Brukstus, IL Farmaco, 59, 255 (2004); doi:10.1016/j.farmac.2003.11.002.
L. Labanauskas, V. Kalcas, E. Uderenaite, P. Gaidelis, A. Brukstus and V. Dauksas, Pharmazie, 56, 617 (2001).
S.A. Almasirad, M. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); doi:10.1016/j.bmcl.2004.09.072.
B. Yang, J. Lin, Y. Chen and Y. Liu, Bioorg. Med. Chem., 17, 6311 (2009); doi:10.1016/j.bmc.2009.07.060.
S. Panda and R. Sahu, Am. J. Adv. Drug Deliv., 1, 1 (2013).
S. Panda and R. Sahu, J. Pharm. Bio. Sci., 9, 30 (2014).
S. Panda and D.L. Singh, World J. Pharm. Pharm. Sci., 3, 1639 (2014).
S. Panda, D.L. Singh and R. Sahu, Int. J. Chem. Pharm. Sci., 4, 1 (2013).
A.A. Abdel-Shafi and S.S. Al-Shihry, Spectrochim. Acta A, 72, 533 (2009); doi:10.1016/j.saa.2008.10.052.
I.V.M.V. Enoch and M.Swaminathan, J. Fluoresc., 14, 751 (2004); doi:10.1023/B:JOFL.0000047226.60559.09.
R. Wang, L. Yuan and D.H. Macartney, Chem. Commun., 5867 (2005); doi:10.1039/b513246k.
M. Maafi, B. Laassis, J.-J. Aaron, M.C. Mahedero, A.M. Peoa and F. Salinas, J. Inclus. Phenom. Mol. Recog.Chem., 22, 235 (1995); doi:10.1007/BF00707086.
W. Misiuk, Indian J. Chem., 51A, 1706 (2012).
R.M. Ahmed, M. Dani and A.A. Elbashir, Int. J. Pharm. Chem. Res., 2, 2278 (2013).
G. Nelson, G. Patonay and I.M. Warner, Anal. Chem., 60, 274 (1988); doi:10.1021/ac00154a018.
S. Panda, S. Nayak and P.K. Das, World J. Pharm. Pharm. Sci., 4, 939 (2015).
T. Higuchi and K.A. Connors, Adv. Anal. Chem. Instrum., 4, 117 (1965).
H. Ueda and T. Endo, Cyclodextrins and their Complexes, Chemistry, Analytical Methods, Applications, Wiley-VCH Verlag, Weinheim, pp. 370 (2006).
H.A. Benesi and J.H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1999); doi:10.1021/ja01176a030.
J. Szetli, Molecular Entrapment and Release Properties of Drugs By Cyclodextrins Controlled Drug Bioavailability, Wiley Interscience, pp. 365-420 (1985).