International Journal of Drug Delivery Technology
Volume 14, Issue 3

Synthesis, Evaluation of Antiangiogenic Activity of Novel Coumarinyl 4-Thiazolidinone Derivatives

Ishwar Bhat K1*, Vijaya Bhaskar K2

1Department of Pharmaceutical Chemistry, NGSM Institute of Pharmaceutical Sciences, Nitte (Deemed to be University), Deralakatte, Mangaluru, Karnataka, India.

2Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal Academy of Higher Education, Manipal, India. 

Received: 16th March, 2024; Revised: 23rd May, 2024; Accepted: 02nd August, 2024; Available Online: 25th September, 2024 

ABSTRACT

Cancer remains in the maximum percentage probability of death in spite of the latest advancement in prior diagnosis and different approaches to treatment. The major challenge in drug discovery for medicinal chemists is to develop new cytotoxic agents to cure cancer with fewer side effects. A new series of substituted coumarinyl 4-thiazolidinone derivatives (TZL1–TZL7) were prepared by treating different 4-hydroxy-3-(1-(phenylimino0ethyl)-2H-chromen-2-one with HSCH2COOH. The Schiff bases were obtained by treating 4-hydroxy coumarin with different aniline derivatives in the presence of C2H5OH. All the title compounds were purified and subjected to TLC to check their purity.

Further, it was characterized by using IR, 1H-NMR, and mass spectral studies. Selected synthesized compounds (TZL1–TZL7) were screened for in-vivo antiangiogenic activity by using the Zebrafish model. TZL2 had the best antiangiogenic effect with an average vein count of 2.7. TZL4, TZL5, and TZL6 had an average vein count of 4.1, 3.9, and 3.4, respectively.

Keywords: Schiff bases, 4-Thiazolidinone, coumarins, Antiangiogenic, Zebrafish. International Journal of Drug Delivery Technology (2024); DOI: 10.25258/ijddt.14.3.41

How to cite this article: Bhat IK, Bhaskar VK. Synthesis, Evaluation of Antiangiogenic Activity of Novel Coumarinyl 4-Thiazolidinone Derivatives. International Journal of Drug Delivery Technology. 2024;14(3):1547-1552.

REFERENCES

  1. Cacić M, Molnar M, Sarkanj B, Has-Schön E, Rajković V. Synthesis and antioxidant activity of some new coumarinyl- 1,3-thiazolidine-4-ones. Molecules. 2010;15 (10): 6795-809. doi:10.3390/molecules15106795.
  2. Todorov L, Saso L, Kostova Antioxidant Activity of Coumarins and Their Metal Complexes. Pharmaceuticals (Basel). 2023;16(5):651. doi: 10.3390/ph16050651
  3. Hamid SJ, Salih T. Design, Synthesis, and Anti-Inflammatory Activity of Some Coumarin Schiff Base Derivatives: In silico and in vitro Study. Drug Des Devel Ther. 2022;16:2275-2288. doi: 10.2147/DDDT.S364746.
  4. Cheke RS, Patel HM, Patil VM, Ansari IA, Ambhore JP, Shinde SD, Kadri A, Snoussi M, Adnan M, Kharkar PS, Pasupuleti VR, Deshmukh PK. Molecular Insights into Coumarin Analogues as Antimicrobial Agents: Recent Developments in Drug Discovery. Antibiotics (Basel). 2022;11(5):566. doi: 10.3390/
  5. Wu Y, Xu J, Liu Y, Zeng Y, Wu G. A Review on Anti-Tumor Mechanisms of Coumarins. Front Oncol. 2020;10:592853. doi: 3389/fonc.2020.592853.
  6. Ranđelović S, Bipat A Review of Coumarins and Coumarin- Related Compounds for Their Potential Antidiabetic Effect. Clin Med Insights Endocrinol Diabetes. 2021;14:11795514211042023. doi: 10.1177/11795514211042023.
  7. Roszczenko P, Holota S, Szewczyk OK, Dudchak R, Bielawski K, Bielawska A, Lesyk R. 4-Thiazolidinone-Bearing Hybrid Molecules in Anticancer Drug Design. Int J Mol Sci. 2022 Oct 28;23(21):13135. doi: 3390/ijms232113135.
  8. Sharma A, Sharma D, Saini N, Sharma SV, Thakur VK, Goyal RK, Sharma PC. Recent advances in synthetic strategies and SAR of thiazolidin-4-one containing molecules in cancertherapeutics. Cancer Metastasis Rev. 2023;42(3):847-889. doi: 10.1007/s10555-023-10106-1.
  9. Kaminskyy D, Kryshchyshyn A, Lesyk 5 -Ene- 4 - thiazolidinones - An efficient tool in medicinal chemistry. Eur J Med Chem. 2017;140:542-594. doi: 10.1016/j.ejmech.2017.09.031.
  10. Siddiqui N, Arshad MF, Khan SA, Ahsan W. Sulfonamide derivatives of thiazolidin-4-ones with anticonvulsant activity against two seizure models: synthesis and pharmacological evaluation. J Enzyme Inhib Med Chem. ;25(4):485-91. doi: 3109/14756360903282833.
  11. Nampurath GK, Mathew SP, Khanna V, Zachariah RT, Kanji S, Chamallamudi MR. Assessment of hypolipidaemic activity of three thiazolidin-4-ones in mice given high-fat diet and fructose. Chem Biol 2008;171(3):363-8. doi: 10.1016/j. cbi.2007.10.006.
  12. Tratrat C, Petrou A, Geronikaki A, Ivanov M, Kostić M, Soković M, Vizirianakis IS, Theodoroula NF, Haroun M. Thiazolidin- 4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Molecules. 2022;27(6):1930. doi: 10.3390/ molecules27061930.
  13. Bhat MA, Al-Omar MA, Naglah AM, Khan AA. Synthesis of Novel Sulfamethaoxazole 4-Thiazolidinone Hybrids and Their Biological Molecules. 2020;25(16):3570. doi: 10.3390/ molecules25163570.
  14. Apotrosoaei M, Vasincu I, Constantin S, Buron F, Routier S, Profire L. Synthesis, characterization and antioxidant activity of some new thiazolidin-4-one derivatives. Rev Med Chir Soc Med Nat Iasi. 2014;118(1):213-8.
  15. Moaz M. Abdou. 3-Acetyl-4-hydroxycoumarin: Synthesis, reactions and application. Arabian J of Chemistry.2007;10: S3664-3675. doi.org/10.1016/j.arabjc.2014.04.005
  16. V. Girgaonkar and S. G. Shirodkar. Synthesis, characterization and Antimicrobial activity of some new Schiff’s bases derived from 3-acetyl-4-hydroxy-2H-chromen-2-one and primary aromatic amines. J Chem Pharm Res, 2012, 4(1):260-264.
  17. Pushkal Samadhiya, Ritu Sharma, S.K. Srivastava, S.D. Synthesis and biological evaluation of 4-thiazolidinone derivatives as antitubercular and antimicrobial agents. Arabian J Chemistry.2014:7(5): 657-65. doi.org/10.1016/j.arabjc.2010.11.015
  18. Seo EJ, Kuete V, Kadioglu O, Krusche B, Schröder S, Greten HJ, Arend J, Lee IS, Efferth T. Antiangiogenic activity and pharmacogenomics of medicinal plants from traditional korean medicine. Evid Based Complement Alternat 2013:131306. doi: 10.1155/2013/131306.