Published October 3, 2024
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Synthesis and preliminary antimicrobial evaluation of new 7-amino-4-methyl-coumarin thiazolidinone conjugates
Authors/Creators
- 1. University of Baghdad, Baghdad, Iraq
- 2. Al-Zahrawi University College, Karbala, Iraq
Description
As a part of our ongoing project on the design and synthesis of new 4-thiazolidinone derivatives with antimicrobial activity, four new 4-thiazolidinone derivatives carrying bromo, nitro, methyl, and chloro groups on the benzene ring were synthesized by starting with the 7-amino-4-methylcoumarin moiety, linking coumarin with various phenyl isothiocynate to form the thiourea group, and then cyclizing the derivatives, characterized by IR and 1HNMR, and assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria and fungi. Overall, 2-(4-methyl-2-oxo-2H-chromen-3-yl)-3-(4-nitrophenyl) thiazolidin-4-one to be the most powerful individuals in the series. Based on the observed data, it can be stated that the synthesized compounds demonstrate a variable range of antibacterial activity.
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References
- Abbas SS, Jasim AM, Shakir TH, Abbas IS (2023) Anticancer activities of some heterocyclic compounds containing an oxygen atom: A review. Al-Rafidain Journal of Medical Sciences 4: 60–67. https://doi.org/10.54133/ajms.v4i.109
- Abd-Elhussain TH, Farhan MS (2024) Synthesis of new pyrimidine derivatives from 3-acetylcoumarin–chalcone hybrid and evaluation their antimicrobial activity. Iraqi Journal of Pharmaceutical Sciences 33(1): 33–45. https://doi.org/10.31351/vol33iss1pp33-45
- Alheety KA, Jamel NM, Tomma JH, Alheety KA (2020) Synthesis and biological activity of some new thiazolidinone derivatives. Systematic Reviews in Pharmacy 11: 490–494.
- Ali AA, Farhan MS (2024) Synthesis, identification and preliminary pharmacological evaluation of new hydrazone and 1, 3, 4-oxadiazole derivatives of ketorolac. Iraqi Journal of Pharmaceutical Sciences 33(1): 113–122. https://doi.org/10.31351/vol33iss1pp113-122
- Archana (2016) Synthesis of newer substituted azetidinone and thiazolidinone derivatives as potent anticonvulsant agents. International Journal of TechnoChem Research 2(2): 121–126.
- Baboo P, Gautam G, Gupta SK (2017) Strategies for the synthesis and biological screening of thiazolidinone derivatives. Asian Journal of Research in Chemistry 10(2): 240. https://doi.org/10.5958/0974-4150.2017.00039.6
- de Souza SM, Delle Monache F, Smânia AJ (2005) Antibacterial activity of coumarins. Zeitschrift für Naturforschung C 60(9–10): 693–700. https://doi.org/10.1515/znc-2005-9-1006
- Farhan MS, Ahmed MH (2021) Synthesis, characterization and anti-inflammatory study of new heterocyclic coumarin derivatives. Indian Journal of Forensic Medicine & Toxicology 15(1): 2363–2369.
- Güzel-Akdemir Ö, Angeli A, Demir K, Supuran CT, Akdemir A (2018) Novel thiazolidinone-containing compounds, without the well-known sulphonamide zincbinding group acting as human carbonic anhydrase IX inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 33(1): 1299–1308. https://doi.org/10.1080/14756366.2018.1499628
- Hassan MZ, Osman H, Ali MA, Ahsan MJ (2016) Therapeutic potential of coumarins as antiviral agents. European Journal of Medicinal Chemistry 123: 236–255. https://doi.org/10.1016/j.ejmech.2016.07.056
- Jain AK, Vaidya A, Ravichandran V, Kashaw SK, Agrawal RK (2012) Recent developments and biological activities of thiazolidinone derivatives: A review. Bioorganic & Medicinal Chemistry 20(11): 3378–3395. https://doi.org/10.1016/j.bmc.2012.03.069
- Kostova I, Bhatia S, Grigorov P, Balkansky S, Parmar VS, Prasad AK, Saso L (2011) Coumarins as antioxidants. Current Medicinal Chemistry 18(25): 3929–3951. https://doi.org/10.2174/092986711803414395
- Kumar R, Patil S (2017) Biological prospective of 4-thiazolidinone: a review. Hygeya: Journal for Drugs and Medicines 9(1): 80–97.
- O'Reilly RA, Aggeler PM, Leong LS (1963) Studies on the coumarin anticoagulant drugs: the pharmacodynamics of warfarin in man. Journal of Clinical Investigation 42(10): 1542–1551. https://doi.org/10.1172/JCI104839
- Omar K, Geronikaki AA, Zoumpoulakis P, Camoutsis C, Soković M, Ćirić A, Glamočlija J (2010) Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorganic & Medicinal Chemistry 18 1: 426–432. https://doi.org/10.1016/j.bmc.2009.10.041
- Pasricha S, Gahlot P (2020) Synthetic strategies and biological potential of coumarin-chalcone hybrids: A new dimension to drug design. Current Organic Chemistry 24(4): 402–438. https://doi.org/10.2174/1385272824666200219091830
- Priya D, Srimathi R (2016) Synthesis and characterization of antimicrobial activity of novel thiazolidinone derivatives of 1,2-benzisoxazole. International Journal of ChemTech Research 9(7): 652–659.
- Prusty JS, Kumar A (2020) Coumarins: antifungal effectiveness and future therapeutic scope. Molecular Diversity 24(4): 1367–1383. https://doi.org/10.1007/s11030-019-09992-x
- Sahu S, Upadhyay PK, Mishra P (2021) An insight into 4-thiazolidinones. Journal of Pharmaceutical Research International 33: 162–174. https://doi.org/10.9734/jpri/2021/v33i45B32793
- Saleh SN, Farhan MS (2023) Synthesis and evaluation of the antimicrobial activity of new different chalcones derived from p-amino benzaldehyde containing thiozolidinone ring. HIV Nursing 23(2): 760–765.
- Salman BS, Ahamad MR (2022) Synthesis and characterization of new thiazolidinone and oxazolidinone heterocyclic derivatives from 2-marcapto-1,3,4-thiadiazole compounds. Chemical Methodologies 6(12): 997–1006.
- Sharabiyani SK, Foroughifar N, Khajeh-Amiri A (2017) Using of some novel derivatives of thiourea for Synthesis of pharmaceutical compounds of 5-Arylidine-2-imino-4-thiazolidinones and their medicinal properties study as anti-inflammatory agents. International Journal of Advanced Engineering Research and Science 4(10): 237281. https://doi.org/10.22161/ijaers.4.10.19
- Tsyalkovsky VM, Kutsyk RV, Matiychuk VS, Obushak ND, Klyufinskaya TI (2005) Synthesis and antimicrobial activity of 5-(R1-benzyl)-2-(R2-benzylidenehydrazono)-3-(2-furylmethyl)Thiazolidin-4-onesT.I.Pharm. Pharmaceutical Chemistry Journal 39: 245–247. https://doi.org/10.1007/s11094-005-0126-8
- Turkovic N, Ivkovic B, Kotur-Stevuljevic J, Tasic M, Marković B, Vujic Z (2020) Molecular docking, synthesis and anti-HIV-1 protease activity of novel chalcones. Current Pharmaceutical Design 26(8): 802–814. https://doi.org/10.2174/1381612826666200203125557