Studies on Inclusion Complexes of 2-(Benzothiazolyl-2')-hydrazono-3-phenyl-5-arylidene-4-thiazolidinone Derivatives with b-Cyclodextrin

S. Dash; R. Sahu; B.K. Garnaik

doi:10.14233/ajchem.2016.20116

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Issue Published : September 1, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Studies on Inclusion Complexes of 2-(Benzothiazolyl-2')-hydrazono-3-phenyl-5-arylidene-4-thiazolidinone Derivatives with b-Cyclodextrin

https://doi.org/10.14233/ajchem.2016.20116

S. Dash

P.G. Department of Chemistry, Berhampur University, Bhanja Bihar-760 007, India

R. Sahu

P.G. Department of Chemistry, Berhampur University, Bhanja Bihar-760 007, India

B.K. Garnaik

P.G. Department of Chemistry, Berhampur University, Bhanja Bihar-760 007, India

Corresponding Author(s) : B.K. Garnaik

bama_61@rediffmail.com

Asian Journal of Chemistry, Vol. 28 No. 12 (2016): Vol 28 Issue 12
Article Published : September 2, 2016

Abstract

A series of 2-(benzothiazolyl-2')-hydrazono-3-phenyl-5-arylidene-4-thiazolidinone derivatives have been synthesized starting from 2-hydrazinobenzothiazole.To enhance the solubility and bioaccessibility of these synthesized pharmacophores the inclusion complexes have been prepared with b-cyclodextrin. The synthesis of compounds and their inclusion complexes have been ascertained from their changes in physical, thermal and spectral characteristics (UV, IR and NMR). The stability constant and free energy change of the inclusion complexes have also been determined. The study suggests that inclusion complexes are appreciably stable and thermodynamically allowed. The synthesized compounds and their inclusion complexes have been screened for their possible antibacterial and antioxidant activities. The results revealed that compounds show better antibacterial and antioxidant activities after inclusion complex formation.

Keywords

4-Thiazolidinone b-Cyclodextrin Phase solubility study Inclusion complexes Antibacterial Antioxidant study

Dash, S., Sahu, R., & Garnaik, B. (2016). Studies on Inclusion Complexes of 2-(Benzothiazolyl-2’)-hydrazono-3-phenyl-5-arylidene-4-thiazolidinone Derivatives with b-Cyclodextrin. Asian Journal of Chemistry, 28(12), 2764–2768. https://doi.org/10.14233/ajchem.2016.20116

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References

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B.K. Garnaik and S. Dash, Asian J. Res. Chem., 7, 1 (2014).
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R. Ottana, R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Sautebin, S. Cuzzocrea and M.G. Vigorita, Bioorg. Med. Chem., 13, 4243 (2005); doi:10.1016/j.bmc.2005.04.058.
A. Kumar, C.S. Rajput and S.K. Bhati, Bioorg. Med. Chem., 15, 3089 (2007); doi:10.1016/j.bmc.2007.01.042.
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B.K. Garnaik and N. Mishra, J. Indian Chem. Soc., 67, 407 (1990).
T. Higuchi and K. Connors, Adv. Anal. Chem. Instum., 4, 117 (1965).
B.K. Garnaik and S. Dash, J. Chem. Pharm. Res., 7, 102 (2015).
S.S. Nayak, S. Panda, P. Panda and M.S. Padhye, Bulg. Chem. Commun., 42, 147 (2010).
B.K. Garnaik, S. Panda and B. Behera, J. Chem. Pharm. Res., 4, 4770 (2012).
V.R. Bollela, D.N. Sato and B.A.L. Fonseca, Braz. J. Med. Biol. Res., 32, 1073 (1999); doi:10.1590/S0100-879X1999000900003.
H.A. Benesi and J.H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1949); doi:10.1021/ja01176a030.
M. Tagashira and Y. Ohtake, Planta Medica, 64, 555 (1998); doi:10.1055/s-2006-957513.
A.P. Mukna and M.S. Nagarsenkar, AAPS Pharm. Sci. Tech., 5, 19 (2001).
J. Szetli, Controlled Drug Bio-availability, Wiley Interscience Publications, New York, vol. 3 (1985).
R.A. Rajewski and V.J. Stella, J. Pharm. Sci., 85, 1142 (1996); doi:10.1021/js960075u.
T. Stalin, P. Vasantharani, B. Shanti, A. Sekhar and N. Rajendiran, Indian J. Chem., 45A, 1113 (2006).
A.V. Astakhova and N.B. Demina, J. Pharma. Chem., 38, 105 (2004); doi:10.1023/B:PHAC.0000032490.04705.ba.

References

K.G. Desai and K.R. Desai, J. Sulfur Chem., 27, 315 (2006); doi:10.1080/17415990600786409.

B.K. Garnaik and S. Dash, Asian J. Res. Chem., 7, 1 (2014).

M.-H. Shih and F.-Y. Ke, Bioorg. Med. Chem., 12, 4633 (2004); doi:10.1016/j.bmc.2004.06.033.

J. Balzarini, B. Orzeszko, J.K. Maurin and A. Orzeszko, Eur. J. Med. Chem., 42, 993 (2007); doi:10.1016/j.ejmech.2007.01.003.

M.V. Diurno, O. Mazzoni, E. Piscopo, A. Calignano, F. Giordano and A. Bolognese, J. Med. Chem., 35, 2910 (1992); doi:10.1021/jm00093a025.

B. Malawska, Curr. Top. Med. Chem., 5, 69 (2005); doi:10.2174/1568026053386944.

S.S. Parmar, C. Dwivedi, A. Chaudhari and T.K. Gupta, J. Med. Chem., 15, 99 (1972); doi:10.1021/jm00271a030.

R. Ottana, R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Sautebin, S. Cuzzocrea and M.G. Vigorita, Bioorg. Med. Chem., 13, 4243 (2005); doi:10.1016/j.bmc.2005.04.058.

A. Kumar, C.S. Rajput and S.K. Bhati, Bioorg. Med. Chem., 15, 3089 (2007); doi:10.1016/j.bmc.2007.01.042.

I. Vazzana, E. Terranova, F. Mattioli and F. Sparatore, ARKIVOC, 364 (2004); doi:10.3998/ark.5550190.0005.531.

Y.R. Prasad, A.L. Rao, L. Prasoona, K. Murali and P.R. Kumar, Bioorg. Med. Chem. Lett., 15, 5030 (2005); doi:10.1016/j.bmcl.2005.08.040.

Z. Ozdemir, H.B. Kandilci, B. Gümüsel, Ü. Calis and A.A. Bilgin, Eur. J. Med. Chem., 42, 373 (2007); doi:10.1016/j.ejmech.2006.09.006.

S. Li and W.C. Purdy, Chem. Rev., 92, 1457 (1992); doi:10.1021/cr00014a009.

B.K. Garnaik and N. Mishra, J. Indian Chem. Soc., 67, 407 (1990).

T. Higuchi and K. Connors, Adv. Anal. Chem. Instum., 4, 117 (1965).

B.K. Garnaik and S. Dash, J. Chem. Pharm. Res., 7, 102 (2015).

S.S. Nayak, S. Panda, P. Panda and M.S. Padhye, Bulg. Chem. Commun., 42, 147 (2010).

B.K. Garnaik, S. Panda and B. Behera, J. Chem. Pharm. Res., 4, 4770 (2012).

V.R. Bollela, D.N. Sato and B.A.L. Fonseca, Braz. J. Med. Biol. Res., 32, 1073 (1999); doi:10.1590/S0100-879X1999000900003.

H.A. Benesi and J.H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1949); doi:10.1021/ja01176a030.

M. Tagashira and Y. Ohtake, Planta Medica, 64, 555 (1998); doi:10.1055/s-2006-957513.

A.P. Mukna and M.S. Nagarsenkar, AAPS Pharm. Sci. Tech., 5, 19 (2001).

J. Szetli, Controlled Drug Bio-availability, Wiley Interscience Publications, New York, vol. 3 (1985).

R.A. Rajewski and V.J. Stella, J. Pharm. Sci., 85, 1142 (1996); doi:10.1021/js960075u.

T. Stalin, P. Vasantharani, B. Shanti, A. Sekhar and N. Rajendiran, Indian J. Chem., 45A, 1113 (2006).

A.V. Astakhova and N.B. Demina, J. Pharma. Chem., 38, 105 (2004); doi:10.1023/B:PHAC.0000032490.04705.ba.

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Studies on Inclusion Complexes of 2-(Benzothiazolyl-2')-hydrazono-3-phenyl-5-arylidene-4-thiazolidinone Derivatives with b-Cyclodextrin

Corresponding Author(s) : B.K. Garnaik

Abstract

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