Antiobesity Evaluation of Novel Series of 3-(5-(Substituted Benzylidene)-2-(Substituted Phenyl)-4-Oxothiazolidin-3-yl)-2-(Substituted Phenyl) Thiazolidin-4-ones

DOI:

https://doi.org/10.37285/ijpsn-aktu.2022-23

Authors

  • Shilpi Chauhan Lloyd Institute of Management and Technology, Greater Noida - 201306, Uttar Pradesh,

Abstract

Introduction: Obesity is a leading disease in developed as well as developing countries due to sedentary lifestyle. Enormous research studies have been ongoing for development of novel antiobesity drugs because orlistat is the only drug approved by Food and Drug Administration (FDA). 

Methods: In the present study, a series of 5-arylidene thiazolidin_4-ones (5a-i) were synthesized by Knoevenagel condensation of corresponding thiazolidinone (4a-e) and aromatic aldehydes in presence of anhydrous sodium acetate. 

Result: The structures of the synthesized compounds were confirmed by spectral 

data i.e. IR and 1H-NMR. All the newly synthesized compounds were evaluated for 

their antiobesity activity. 

Conclusion: All the synthesized compounds significantly reduced the body weight gain. Among all the compounds, 5h and 5i were found to most active, almost comparable to orlistat.

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Keywords:

5-Arylidene thiazolidin-4-one, anti-obesity activity, aromatic aldehydes, Knoevenagel condensation, Orlistat

Published

2023-09-15

How to Cite

1.
Chauhan S. Antiobesity Evaluation of Novel Series of 3-(5-(Substituted Benzylidene)-2-(Substituted Phenyl)-4-Oxothiazolidin-3-yl)-2-(Substituted Phenyl) Thiazolidin-4-ones. Scopus Indexed [Internet]. 2023 Sep. 15 [cited 2024 Sep. 8];15(7):6809-17. Available from: http://ijpsnonline.com/index.php/ijpsn/article/view/4840

References

Roger AHA, Louk JMJ, Vanderschuren, Susanne ELF. Anti-obesity drugs and neural circuits of feeding. Trends in Pharmacological Sciences. 2008;29:208-217.

Ali AT, Crowther NJ. Factors predisposing to obesity: a review of the literature. Journal of Endocrinology, Metabolism and Diabetes of South Africa. 2009;14:81-84.

Michael AV, Jieru EL, Scott AW. Central and peripheral molecular targets for anti-obesity pharmacotherapy. Clinical Pharmacology & Therapeutics. 2010;87:652-662.

Vigorita MG, Ottana R, Monforte F, Maccari R, Trovato A, Monforte MT, Traviano MF. Synthesis and anti-inflammatory, analgesic activity of 3,3’-(1,2-Ethanediyl)-bis[2-aryl-4-thiazolidin- one] chiral compounds. Bioorganic & Medicinal Chemistry Letters. 2001;11:2791-2794.

Kavitha CV, Basappa S, Swamy N, Mantelingu K, Doreswamy S, Sridhar MA, Prasad S, Rangappa KS. Synthesis of new bioactive venlafaxine analogs: Novel thiazolidin-4-ones as antimicrobials. Bioorganic & Medicinal Chemistry. 2006;14:2290-2299.

Sobin BA. Novel inhibitors of an emerging target in Mycobacterium tuberculosis,substituted thiazolidinones as inhibitors of dTDP-rhamnose synthesis. Journal of the American Chemical Society. 1952;74:2946-2947.

Badaoglu K, Page MA, Jones VC, Mc. Neil MR, Dong C, Nai smith JH, Lee RE. Ultrasound-assisted synthesis of 2,4-thiazolidine-dinone and rhodanine derivatives catalysed by task-specific ionic liquid : [TMG][Lac]. Bioorganic & Medicinal Chemistry Letters. 2003;13:3227.

Türe A, Ergül M, Ergül M, Altun A, Küçükgüzel İ. Design, synthesis, and anticancer activity of novel 4-thiazolidinone-phenylaminopyrimidine hybrids. Molecular Diversity. 2021;25(2):1025-1050.

Kumar S, Kudva J, Bharath BR, Ananda K, Sadashiva R, Kumar SM, Revanasiddappa BC, Kumar V, Rekhah PD, Narali D. Synthesis, structural, biological and in silico studies of new 5-arylidene-4-thiazolidinone derivatives as possible anticancer, antimicrobial and antitubercular agents. New Journal of Chemistry. 2019;43:1597-1610.

Raghubir R, Verma R, Samuel SS, Raza S, Haq W, Katti SB. Anti-stroke profile of thiazolidin-4-one derivatives in focal cerebral ischemia model in rat. Chemical Biology & Drug Design. 2011;78(3):445-53.

Konstantinos LID, Maria FID, Athina G. Thiazoles and Thiazolidinones as COX/LOX Inhibitors. Molecules 2018;23:685.

Diurno MV, Mazzoni O, Calignano PE, Giordano F, Bolognese A. Synthesis and antihistaminic activity of some thiazolidin-4-ones. Journal of Medicinal Chemistry. 1992;35:2910.

Suryawanshi R, Jadhav S, Makwana N, Desai D, Chaturbhuj D, Sonawani A, Idicula-Thomas S, Murugesan V, Katti SB, Tripathy S, Paranjape R, Kulkarni S. Evaluation of 4-thiazolidinone derivatives as potential reverse transcriptase inhibitors against HIV-1 drug resistant strains. Bioorganic Chemistry. 2017;71:211-218.

Tanabe Y, Suzukamo G, Komuro Y, Imanishi NS, Morooka SM, Enomoto M, Kojima A, Sanemitsu Y, Mizutani M. Structure-activity relationship of optically active 2-(3-pyridyl) thiazolidin-4-ones as a PAF antagonist. Tetrahedron Letters. 1991;32:379-382.

Knutsen LJ, Hobbs CJ, Earnshaw CG, Fiumana A, Gilbert J, Mellor SL, Radford F, Smith NJ, Birch PJ, Russell Burley J, Ward SD, James IF. Synthesis and SAR of novel 2-arylthiazolidinones as selective analgesic N-type calcium channel blockers. Bioorganic & Medicinal Chemistry Letters. 2007;17(3):662-667.

Drapak I, Perekhoda L, Demchenko N, Suleiman M, Rakhimova M, Demchuk I, Taran S, Seredynska N, Gerashchenko I. Cardioprotective activity of some 2-arylimino-1,3-thiazole derivatives. Scientia Pharmaceutica. 2019;87:7.

Kármen S, Rosanna M, Rosaria O, Gyöngyi G. Extending the investigation of 4-thiazolidinone derivatives as potential multi-target ligands of enzymes involved in diabetes mellitus and its long-term complications: A study with pancreatic α-amylase. Carbohydrate Research. 2021;499:108220.

Mohammed Iqbal AK, Khan AY, Kalashetti MB, Belavagi NS, Gong Y-D, Khazi IAM. Synthesis, hypoglycemic and hypolipidemic activities of novel thiazolidinedione derivatives containing thiazole/triazole/oxadiazole ring. European Journal of Medicinal Chemistry. 2012;53:308-315.

Jacob N, Kutty GN. Synthesis and Hypolipidemic activity of a thiazolidinone derivative. Indian Drugs 2004;41:76-79

Bondock S, Fouda AM. Synthesis and evaluation of some new 5-(hetaryl)thiazoles as potential antimicrobial agents. Synthetic Communications. 2018;48:561–573.

Friedewald WT, Levy RI, Fredrickson DS. Estimation of the concentration of low-density lipoprotein cholesterol in plasma, without use of the preparative ultracentrifuge. Clinical Chemistry. 1972;18:499-502.

Pareek D, Chaudhary M. Synthesis and biological evaluation of thiazolidinone derivatives incorporating benzothiazole moiety. Der Pharmacia Sinica 2011;2:170-181.

Shrivastava SP, Seelam NV, Rai R. Synthesis and antimicrobial activity of new thiazolidinone derivatives with the use of γ-Ferrite catalyst. E-Journal of Chemistry 2012;9:825-831.

Ghosh G, Kadam PP, Kadam VJ. Antioxidant and hypolipidemic activity of kumbhajatu in hypercholesterolemic mice. International Journal of Ayurveda Research 2010;1:159-162.

Xia D, Wu X, Yang Q, Gong J, Zhang Y. Anti-obesity and hypolipidemic effects of a functional formula containing Prumusmume in mice fed high-fat diet. African Journal of Biotechnology. 2010;9:2463-2467.

Rifai N, Bachorik PS, Albers JJ. Lipids, Lipoproteins, and apolipoproteins. In:Burtis. Text book of clinical chemistry. 1999:809–861.

Burstein M, Scholnick HR, Morfin R. Method for isolation of lipoproteins from human serum by precipitation with polyanions. Journal of Lipid Research 1970;11:583–595.