Asian Journal of Research in Chemistry

Open Access Open Access  Restricted Access Subscription Access
Open Access Open Access Open Access  Restricted Access Restricted Access Subscription Access

Studies of thermal, spectral and antibacterial activities of some inclusion complexes of 4-Thiazolidinone derivatives with β-Cyclodextrin


Affiliations
1 Department of Chemistry, Roland Institute of Technology, Berhampur, Odisha, India, India
     

   Subscribe/Renew Journal


2-Hydrazinobezothiazole is taken as starting material for the preparation of some compounds of 4-thazolidinone derivative. 4-Thiazolidinone and its analogous are very good pharamacophores performing wide range of biological activities. But the compounds being poor solubility in aqueous medium may be a limiting factor for decreasing their bio-accessibility. To removes the difficulties, its inclusion complexes can be prepared with βcyclodextrin which is non-toxic oligosaccharide. The nature of inclusion complexes along with the compounds characters such as physical, spectral and thermal are discussed. The stoichiometry ratio of 1:1 between the compound and β-cyclodextrin confirmed from their aqueous phase solubility study. The existence of weak intermolecular force between 4-thiazolidinone derivatives and β-cyclodextrin can be ascertained from their thermodynamic stability constants. The antibacterial activity against the microbes like E.coli and S.aureus are susceptible to compounds of 4-thiazolidinone, and it enhances in their corresponding inclusion complexes. The stability of inclusion complex and host–guest relation can be ascertained from thermodynamic parameters along with the free energy change. Besides this, there is alternation in physical and spectral properties of compounds after formation of inclusion complexes.

Keywords

2-Hydrazinobezothiazole, Phase solubility, Host-guest, Stability constant.
Subscription Login to verify subscription
User
Notifications
Font Size


  • Patil ST and Bhatt PA, Synthesis and biological evaluation of some novel 2-(4-substituted phenyl)-3-(4-substituted phenyl)-5methylthiazolidine-4-ones, Inter. J. Pharm. and Tech., 2010 ;2(3); 674-682.

  • Yadav R., Srivastava SD and Srivastava SK, Synthesis, antimicrobial and anti-inflammatory activities of 4oxothiazolidines and their 5-arylidenes, Indian J. Chem., 2005; 44B:1262-1266.

  • Rao BP, Suresh S and Narendra C, Recent advances in cyclodextrin complexes: Mechanistic analysis as permeation enhancer, Indian J. Pharm. Educ. Res, 2007; 41(2): 102-113.

  • Carrier RL, Miller LA and Ahmed I, The utility of cyclodextrins for enhancing oral bioavailability, J. Contr. Drug. Rel, 2007;123; 78-99.

  • Brewster ME and Loftsson T, Cyclodextrins as pharmaceutical solubilizers, Adv. Drug Deliv .Rev., 2007;59;645-666.

  • Deep A, Jain S, Sharma PC, Mittal SK, Phogat P and Malhotra M, Synthesis, characterization and antimicrobial evaluation of 2,5disubstituted-4-thiazolidinone derivatives, Arab. J. Chem., 2014; 7(3); 287–291.

  • Cheddie A, Shintre SA, Bantho A, Mocktar C and Koorbanally N.A., Synthesis and antibacterial activity of a series of 2trifluoromethylbenzimidazole-thiazolidinone derivatives, J. Hetero. Chem., 2020; 57 (1); 299–307.

  • Güzeldemirci NU, Pehlivan E and Naesens L, Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo2,1-b. thiazole moiety, Marmara Pharm. J., 2018; 22 (2), 237– 248.

  • Mishchenko M, Shtrygol S, Kaminskyy D and Lesyk R, Thiazolebearing 4 thiazolidinones as new anticonvulsant agents, Sci.Pharm., 2020; 88(1); 16-30.

  • Rohini RM and Manjunath M, Synthesis and anti-convulsant activity of triazothiole/thiazolyl thiazolidinone derivatives of indole, Der Pharma Chemica., 2012;4 (6): 2438–2441.

  • Anekal DP and Biradar JS, Synthesis and biological evaluation of novel Indolyl 4-thiazolidinones bearing thiadiazine nucleus, Arab. J. Chem., 2017;10 (Suppl 2): S2098–S2105.

  • Shinde RS, Masand VH and Patil MK, Anti-inflammatory activity of triazine thiazolidinone derivatives, molecular docking and pharmacophore modelling, Indian J. Pharm. Sci., 2019; 81(5), 851–858.

  • Gawrońska-Grzywacz M, Popiołek Ł, Natorska-Chomicka D, Piątkowska-Chmiel I, Izdebska M and Herbet M, Novel 2,3disubstituted 1,3-thiazolidin-4-one derivatives as potential antitumor agents in renal cell adenocarcinoma, Oncol. Rep., 2019; 41(1): 693–701.

  • Mushtaque M, Avecilla F, Hafeez ZB and Rizvi MMA, Synthesis, characterization, molecular docking, and anticancer evaluation of 4-thiazolidinone analogues, J. Hetero. Chem., 2019; 56(6): 1794– 805.

  • Holota S, Kryshchyshyn A, Derkach H, Trufin ., Demchuk I and Gzella A, Synthesis of 5-enamine-4-thiazolidinone derivatives with trypanocidal and anticancer activity, Bioorg. Chem., 2019; 86: 126–136.

  • Ekinci AS, Moncol J, Krishna VS, Sriram D and Özadali-Sari K.5-Methyl-4- thiazolidinones, Synthesis and evaluation as antitubercular agents, J. Res. Pharm., 2020; 24(1): 30–37.

  • Abo-Ashour MF, Eldehna WM, George RF, Abdel-Aziz MM, Elaasser MM and Abou Seri SM, Synthesis and biological evaluation of 2-aminothiazole-thiazolidinone conjugates as potential antitubercular agents, Future Med. Chem.,2018; 10(12):1405–1419.

  • Rajendra PY,Lakshmana RA, Prasoona L, Murali K and Rav KP;Synthesis and characterization of 1-formyl-3-phenyl-5-uryl- 2pyrazolines, Bio.Med.Chem.Lett., 2005;15: 5030-5034.

  • Ozdemir Z, Kandilici HB, Gumusel B, Calis U and Bilgin, AA, Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives, Eur.J.Med.Chem., 2007;42: 373-379.

  • Li S and Purdy WC, Cyclodextrins and their application in analytical chemistry, Chem.Rev., 1992;92: 1457-1470.

  • Garnaik BK, Mishra N, Sen M and Nayak A, Synthesis of 4thiaziazolidinone by using Schiff’s base, J.Indian Chem. Soc., 1990;67: 407-408.

  • Higuchi T. and Connors K, Phase solubility technique, Adv. Anal.Chem. Instru., 1965; 4: 117-211.

  • Sahu R, Dash S and Garnaik BK, Thermal, Spectral, Antibacterial and Antioxidant Studies on Inclusion Complexes of 2(Benzothiazolyl-2’)hydrazono-3-phenyl 5-arylidene- 4Thiazolidinone derivatives with β-cyclodextrin, Res. J. Pharm.Tech., 2016; 9(12): 2265-2270.

  • Dash S, Sahu R and Garnaik BK, Studies on Inclusion complexes of 2-(Benzothiazolyl-2’)hydrazono-3-phenyl-5-arylidene-4Thiazolidinone derivatives with β cyclodextrin, Asian J. Chem., 2016; 28(12):2764-2768 .

  • Panda S, Nayak SS, Panda PM and Padhy S, Studies on acridone derivatives with and without inclusion complex formation with βcyclodextrin, Bull. Chem. Comm., 2010;42(2):147-152.

  • Dash S, Inclusion Complexes of Some Substituted 4- Thiazolidinones with Activating and Deactivating Group, Asian J. Chem., 2020; 32(1): 133-136.

  • Bollela VR, Sato DN and Fonseca BAL., McFarland nephelometer as a simple method to estimate the sensitivity of the polymerase chain reaction using Mycobacterium tuberculosis as a research

  • tool, Brazi. J.Med.Bio.Res., 1999; 32: 1073-1076.

  • Szetli J, Molecular entrapment and release properties of drugs by cyclodextrins. Controlled Drug Bio-availability. 1985; Vol. 3:Willey Interscience publications, New York.

  • Rajewski RA and Stella VJ, Pharmaceutical applications of cyclodextrins in vivo drug delivery, Jour. of Pharma., 1996; 85: 1142-1169.

  • Stalin T., Vasantharani P, Shanti B, Sekhar A and Rajendiran N, Inclusion Complexes of trihydroxybenzene with α- and βcyclodextrin, Ind. J. Chem. Sec A., 2006;45: 1113-1120.

  • Benesi HA and Hilderband JH, A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons, J. Amer. Chem. Soc. 1999;71: 2703-2707.


Abstract Views: 122

PDF Views: 0




  • Studies of thermal, spectral and antibacterial activities of some inclusion complexes of 4-Thiazolidinone derivatives with β-Cyclodextrin

Abstract Views: 122  |  PDF Views: 0

Authors

Simanchal Dash
Department of Chemistry, Roland Institute of Technology, Berhampur, Odisha, India, India

Abstract


2-Hydrazinobezothiazole is taken as starting material for the preparation of some compounds of 4-thazolidinone derivative. 4-Thiazolidinone and its analogous are very good pharamacophores performing wide range of biological activities. But the compounds being poor solubility in aqueous medium may be a limiting factor for decreasing their bio-accessibility. To removes the difficulties, its inclusion complexes can be prepared with βcyclodextrin which is non-toxic oligosaccharide. The nature of inclusion complexes along with the compounds characters such as physical, spectral and thermal are discussed. The stoichiometry ratio of 1:1 between the compound and β-cyclodextrin confirmed from their aqueous phase solubility study. The existence of weak intermolecular force between 4-thiazolidinone derivatives and β-cyclodextrin can be ascertained from their thermodynamic stability constants. The antibacterial activity against the microbes like E.coli and S.aureus are susceptible to compounds of 4-thiazolidinone, and it enhances in their corresponding inclusion complexes. The stability of inclusion complex and host–guest relation can be ascertained from thermodynamic parameters along with the free energy change. Besides this, there is alternation in physical and spectral properties of compounds after formation of inclusion complexes.

Keywords


2-Hydrazinobezothiazole, Phase solubility, Host-guest, Stability constant.

References