S. Ramachandran, Binoy Varghese Cheriyan, M. Vijey Aanandhi
S. Ramachandran*, Binoy Varghese Cheriyan, M. Vijey Aanandhi
Department of Pharmaceutical Analysis, Vels Institute of Science Technology and Advanced Studies, Pallavaram, Chennai - 600117, India.
Volume - 14,
Issue - 8,
Year - 2021
Thiazolidine-4-ones containing thiazole moiety have been synthesized by condensing 6-amino Coumarin, Isatin and Primary amines, and aromatic aldehydes. Azetidine derivates were synthesized followed by cyclizations by C-N bond formation and by the C-C bond formation, the amine-catalyzed cycloaddition of allenoates and imines, photocycloadditions of imines and alkenes, ring contraction and expansion rearrangements, and reduction of azetidine-2-ones (ß-lactams). Thiazolidine-4-ones has been considered as a magic moiety because it posses almost all types of biological activities such as Antifungal, Antitubercular, Antimicrobial, Antioxidant, Antibacterial, Cytotoxic, Anti-inflammatory, Analgesic, Anti YFV (yellow fever virus) activities. Azetidine-2-one derivatives were reported to possess antibacterial, antifungal and antidepressant activity, anticonvulsant activity, anti-inflammatory activity and cardiovascular activities, antimycobacterial activity, antihypertensive activity. This article is a review of various biological activities of thiazolidine-4-ones and Azetidine-2-ones derivatives
Cite this article:
S. Ramachandran, Binoy Varghese Cheriyan, M. Vijey Aanandhi. Activities of Thiazolidine-4-one and Azetidine-2-one Derivatives- A Review. Research Journal of Pharmacy and Technology. 2021; 14(8):4513-6. doi: 10.52711/0974-360X.2021.00785
S. Ramachandran, Binoy Varghese Cheriyan, M. Vijey Aanandhi. Activities of Thiazolidine-4-one and Azetidine-2-one Derivatives- A Review. Research Journal of Pharmacy and Technology. 2021; 14(8):4513-6. doi: 10.52711/0974-360X.2021.00785 Available on: https://www.rjptonline.org/AbstractView.aspx?PID=2021-14-8-91
1. Mulay Abhinit, Mangesh Ghodke, Nikalje Anna Pratima. Exploring the potential of 4- thiazolidinediones: A brief review. International Journal of Pharmacy and Pharmaceutical Science, 2009, (1): 57-64
2. Jubie S, Gowramma B, Nitin KM, Jawahar N, Kalirajan R, Gomathy S. Synthesis and biological evaluation of some 3-(methoxyphenyl)-2-aryl Thizolidin-4-one derivatives. Ind J Pharma Sci. 2009, 1 (1): 32-38
3. Gurupadyya BM, Gopal M, Padmashali B, and Manohara YN. Synthesis and pharmacological evaluation of azetidine-2-ones and thiazolidin-4-ones encompassing benzthiazole. Ind J Pharm Sci, 2008, 70 (5): 572-577.
4. Visagaperumal D, R Jaya Kumar, R Vijayaraj, N Anbalgan. Microwave induced synthesis of some new 3- substituted-1,3-thiazolidine-4-ones for their potent antimicrobial and antitubercular activities. Int J Chem Tech Res. 2009, 1(4): 1048-1051.
5. Ketan Mistry and K R Desai. Microwave-assisted rapid and efficient synthesis of nitrogen and sulphur containing heterocyclic compounds and their pharmacological evaluation. Ind J Chem, 2006, 45(B): 1762-1766.
6. Sharanabasppa B Patil, Naganna M Goudgaon. Synthesis of 3-(1-benzyl-1H-benzo[D] imidazole-2-L-amino)-2-(3-Aryl-1-phenyl-1H-pyrazol-4-yl) Thiazolidine-4-one and their antimicrobial activities. I J P S R, 2010, (1): 50-60.
7. Milan Cacic, Maja Molnar and Nela Draca. Design and synthesis of some thiazolidine- 4-ones based on (7-hydroxy-2-oxo-2H-chromen-4-yl) acetic acid. Molecule. 2009, 14: 2501-2513.
8. Parmeshwaran Manojkumar, Gopalkrishnan Subbuchettiar. Synthesis of coumarinheterocyclic derivatives with antioxidant activity and in-vitro cytotoxic activity against tumor cells. Acta Pharm. 2009, 59: 159-170.
9. Vandana Tiwari, Jyotsna Meshram, Parvez Ali. Microwave-assisted synthesis of quinolinyl thiazolidinediones using Zeolite as an efficient and recyclable activation surface: SAR and Biological activity. Der Pharma Chemica. 2010, 2 (3): 187-195.
10. Shiva P. Singh, Surendra. S. Parmar, Krishna Raman, Virgin I. Stenberg, Chemistry and biological activity of thiazolidinones, Chem. Rev.81(2), 175-203 (1981).
11. Jubie S, Gowramma B, Nitin KM, Jawahar N, Kalirajan R, Gomathy S. Synthesis and biological evaluation of some 3-(methoxyphenyl)-2-aryl Thizolidin-4-one derivatives. Ind J Pharma Sci. 2009, 1 (1): 32-38
12. Ranjana Sharma, Devendra P. Nagda, and Ganpat L. Talesara. Synthesis of various isoniazidothiazolidinones and their imidoxy derivatives of potential biological interest. ARKIVOC. 2006, 1: 1-12
13. Devprakash and Udaykumar A Bhoi, A complete review of thiazolidine-4-ones. Journal of Pharmacy Research. 2011, 4(7), 2436-2440
14. S. Ramachandran, R. Sundhararajan, Synthesis, Characterization, Antimicrobial evaluation of 2-hydroxy Phenyl thiazolidine-4-one derivative in World Journal of Pharmacy and Pharmaceutical Sciences. 2017, 6(8), 278-283
15. K H Patel and A G Mehta. E-Journal of Chemistry. Vol. 3, No.11, 103-109(2006).
16. Desai KG, Desai KRJ, A facile microwave enhanced synthesis of sulfur-containing 5-membered heterocycles derived from 2-mercaptobenzothiazole over ZnCl2/DMF and antimicrobial activity evaluation. Sulfur Chemistry. 2006; 27(4): 315-328.
17. Bhoot DP, Khunt RC, Shankhavara VK, Parekh HH, Journal of Sciences.2006; 17(4): 323-325.
18. H. Bhaskar, M. Kumar, B. Sangameswaran and B. R. Balakrishnan, Antimicrobial activity of Some 4-thiazolidine derivatives. International Bi-annual Journal. 2009.
19. P. Shanmugapandiyan, A. Ramesh Organic chemistry-an Indian Journal, 2008: 1-8
20. P. Shanmugapandiyan , K.S. Denshing, R. Ilavarasan, N. Anbalagan, R. Nirmal. International Journal of Pharmaceutical Sciences and Drug Research. 2010; 2(2): 115-119.
21. Alegaon SG, Alagawadi KR, Vinod D, Unger B, et al. Synthesis, pharmacophore modeling, and cytotoxic activity of 2-thioxothiazolidin-4-one derivatives. Medicinal Chemistry Research. 2014
22. Eleftheriou P, Geronikaki A, Hadjipavlou-Latina D, Vicini P, et al. Fragment-based design, docking, synthesis, biological evaluation and structure-activity relationships of 2- benzo/benzisothiazole imino-5-aryliden-4-thiazolidinones as cyclooxygenase/ lipoxygenase inhibitors. European Journal of Medicinal Chemistry. 2012; 47: 111-24.
23. Nasr T, Bondock S, Eid S. Design, synthesis, antimicrobial evaluation and molecular docking studies of some new 2,3-dihydrothiazoles and 4-thiazolidinones containing sulfisoxazole. Journal of Enzyme Inhibition and Medicinal Chemistry. 2015; 01-11.
24. Unsal-Tan O, Ozadali K, Piskin K, Balkan A. Molecular modeling, synthesis and screening of some new 4-thiazolidinone derivatives with promising selective COX-2 inhibitory activity. European Journal of Medicinal Chemistry. 2012; 57: 59-64.
25. Havrylyuk D, Zimenkovsky B, Vasylenko O, Day CW, et al. Synthesis and Biological Activity Evaluation of 5-Pyrazoline Substituted 4-Thiazolidinones. European Journal of Medicinal Chemistry. 2013; 05-44
26. Kuçukguzel I, Satılmış G, Gurukumar KR, Basu A, et al. 2-Heteroarylimino-5-arylidene-4- thiazolidinones as a new class of non-nucleoside inhibitors of HCV NS5B polymerase. European Journal of Medicinal Chemistry. 2013; 08-43
27. Ref Alegaon SG, Alagawadi KR, Pawar SM, Vinod D, et al. Synthesis, Characterization and biological evaluation of thiazolidine-2, 4-dione derivatives. Medicinal Chemistry Research. 2013.
28. Vicini P, Geronikaki A, Incerti M, Zani F, et al. 2-Heteroarylimino-5-benzylidene-4- thiazolidinones analogs of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: Synthesis and structure-activity relationship. Bioorganic and Medicinal Chemistry. 2008; 16: 3714-24.
29. Aneja DK, Lohan P, Arora S, Sharma C, et al. Synthesis of new pyrazolyl-2, 4- thiazolidinediones as antibacterial and antifungal agents. Organic and Medicinal Chemistry Letters. 2011; 1: 15.
30. Babaoglu K, Page MA, Jones VC, McNeil MR, et al., Novel inhibitors of an emerging target in Mycobacterium tuberculosis; substituted thiazolidinones as inhibitors of dTDP- rhamnose synthesis. Bioorganic and Medicinal Chemistry Letters. 2003; 13: 3227-30.
31. Malipeddi H, Karigar AA, Malipeddi VR, Sikarwar MS. Synthesis and antitubercular activity of some novel thiazolidinone derivatives. Tropical Journal of Pharmaceutical Research. 2012; 11(4): 611-20.
32. Cheptea C, Dulcescu MM, Dorohoi DO, Valeriu S, et al. Design, Synthesis and Molecular Modelling of New Thiazolidines 2,3-disubstituted with Antitumoral Activity. Digest Journal of Nanomaterials and Biostructures. 2012; 7(1): 287-97.
33. Bhaumik A, Chandra MA, Saha S, Mastanaiah J, et al. Synthesis, characterization and evaluation of anticonvulsant activity of some novel 4-thiazolidinone derivatives. Scholars Academic Journal of Pharmacy. 2014; 3(2): 128-32.
34. Ravindra Kumar, AbhaShuklab, and D.S. Tyagi.Synthesis of Bioactive Azetidinones of 4-Phenyl-1, 3-thiazole-2-amine. Chem Sci Trans. 2013; 2(4): 1518-1522.
35. Havaldar FH, Bhise SS, Burudkar SM. Convenient synthesis and biological activity of 2-azetidinones and 4-thiazolidinediones. Indian J Heterocyclic Chem. 2005; 14: 297-300.