2-(3-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones as Potent Antioxidant and Antidiabetic Agent

Sandip Sen; Biplab De; T.S. Easwari

doi:10.14233/ajchem.2014.17003

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

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

2-(3-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones as Potent Antioxidant and Antidiabetic Agent

https://doi.org/10.14233/ajchem.2014.17003

Sandip Sen

IIMT College of Medical Sciences, O. Pocket, Ganga Nagar, Meerut-250 001, India

Biplab De

Regional Institute of Pharmaceutical Science and Technology, Abhoynagar, Agartala-799 006, India

T.S. Easwari

IIMT College of Medical Sciences, O. Pocket, Ganga Nagar, Meerut-250 001, India

Corresponding Author(s) : Sandip Sen

sandipsen2010@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 19, 2014

Abstract

A series of 2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones (7a-7j) were synthesized by intramolecular cyclization of imines (6a-6j) with thioglycolic acid in the presence of acid catalyst. The Schiff bases were obtained upon reaction between electrophilic carbon atom of 3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (4) and nucleophilic nitrogen atom of substituted aromatic amines. in vitro Antioxidant activity was determined by DPPH redical scavenging assay mehod using ascorbic acid as standard. The antidiabetic activity was carried out by streptazocine induced diabetic method using rosiglitazone as standard drug on wister rats. From the study it were found that 3-(4-chlorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7a), 3-(4-bromophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7b), 3-(3,4-dichlorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7d), 3-(3,4-difluorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7f) 2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(4-(trifluoromethyl)phenyl)thiazolidin-4-one (7h), 3-(4-methoxyphenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7j) shown more IC₅₀ compare to standard. Where as compound 7a, 7b, 7h, 7j show more significant antidiabetic effect against hyperglycemic rats compare to standard drugs at the dose of 5 mg/kg after 21 days of treatment.

Keywords

Pyrazole-4-carboxaldehydes Thiazolidine-4-one Antioxidant Antidiabetic

Sen, S., De, B., & Easwari, T. (2014). 2-(3-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones as Potent Antioxidant and Antidiabetic Agent. Asian Journal of Chemistry, 26(19), 6616–6622. https://doi.org/10.14233/ajchem.2014.17003

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References

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M. Burstein, H.R. Scholnick and R. Morfin, J. Lipid Res., 11, 583 (1970).
M. Imran, B. Ilyas and S.A.K. Deepanjali, J. Sci. Ind. Res. (India), 66, 99 (2007).

References

E.M. Sharshira and N.M.M. Hamada, Molecules, 17, 4962 (2012); doi:10.3390/molecules17054962.

M.R. Chaurasia, Indian J. Pharm., 33, 17 (1971).

B. Zimenkovsky, R. Lesyk, O. Vladzimirska, I. Nektegayev, S. Golota and I. Chorniy, J. Pharm. Pharmacol., 51, 264 (1999).

A.R. Saltiel and J.M. Olefsky, Diabetes, 45, 1661 (1996); doi:10.2337/diab.45.12.1661.

S. Schwartz, P. Raskin, V. Fonseca and J.F. Graveline, N. Engl. J. Med., 338, 861 (1998); doi:10.1056/NEJM199803263381302.

J. Buse, B. Gumbiner, N.P. Mathias, D.M. Nelson, B.W. Faja, R.W. Whitcomb, The Troglitazone Insulin Study Group, Diabetes Care, 21, 1455 (1998); doi:10.2337/diacare.21.9.1455.

D. Quilliot, E. Walters, J.-P. Bonte, J.-C. Fruchart, P. Duriez and O. Ziegler, Am. J. Clin. Nutr., 81, 1117 (2005).

B.S. Furniss, A.J. Hannaford, P.W.G. Smith and A.R. Tetchell, Vogels Text Book of Practical Organic Chemistry, Longman Ltd., England, edn. 5, pp. 243-244, 1150 (1998).

R.M. Ambika Srivastava Singh, Indian J. Chem., 44B, 1868 (2005).

Y. Li, Z.S. Yang, H. Zhang, B.J. Cao, F.D. Wang, Y. Zhang, Y.-L. Shi, J.-D. Yang and B.-A. Wu, Bioorg. Med. Chem., 11, 4363 (2003); doi:10.1016/S0968-0896(03)00499-1.

W. Brand Willams, M.E. Cuvelier and C. Berset, Lebensm.-Wissen. Technol., 28, 25 (1995).

J.C. Espin, C. Soler Rivas and H.J. Wichers, J. Agric. Food Chem., 48, 648 (2000); doi:10.1021/jf9908188.

OECD, Guidelines No. 423 for the Testing of Chemicals Revised Draft Guideline 423 Acute Oral Toxicity, Paris (2000).

S.V. Kadnur and R.K. Goyal, Indian J. Pharm. Sci., 67, 453 (2005).

T.S. Frode and Y.S. Medeiros, J. Ethnopharmacol., 115, 173 (2008); doi:10.1016/j.jep.2007.10.038.

N. Rifaci, P.S. Bachorik and J.J. Albers, in eds.: ln C.A. Burtis and E.R. Ashwood, Lipid, Lipoprotein and Apolipoprotein, Tretz Text Book of Clinical Chemistry, WB Saunder Company, Philadolphia, edn. 3, pp. 809-861 (1999).

R.P. MacDonald, Standard Methods of Clinical Chemistry, Academic Press, New York, pp. 215-222 (1953).

L. Thomas, Clinical Laboratory Dragnostics, TH Book Verlasgesell schaft, Frankfurt, pp. 208-214, 366-374 (1998).

N.W. Tretz, Text Book of Clinical Chemistry, WB Saumder Company, Philadelphia, edn. 3, p. 579 (1986).

M. Burstein, H.R. Scholnick and R. Morfin, J. Lipid Res., 11, 583 (1970).

M. Imran, B. Ilyas and S.A.K. Deepanjali, J. Sci. Ind. Res. (India), 66, 99 (2007).

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

2-(3-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones as Potent Antioxidant and Antidiabetic Agent

Corresponding Author(s) : Sandip Sen

Abstract

Keywords

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