A review of recent research on the antimicrobial activities of thiosemicarbazone-based compounds

Yıl 2024, , 61 - 83, 30.04.2024

Gürsel Korkmaz

https://doi.org/10.54187/jnrs.1464723

Cited By: 2

Öz

Thiosemicarbazones can be synthesized by condensation of thiosemicarbazides with ketones or aldehydes and play a role as precursors in the synthesis of many compounds such as thiazoles. They can exhibit many biological activities such as anti-inflammatory, antitumor, and antimicrobial properties. The discovery of antibiotics was an important milestone in the treatment of bacterial infections. However, antimicrobial resistance developed by microorganisms has created the need to discover new antimicrobial agents. Thiosemicarbazones and thiosemicarbazone-based compounds show significant antimicrobial potential. This review investigates the antimicrobial activity results of 244 Thiosemicarbazones and Thiosemicarbazone-based compounds over the last five years. We summarized some articles on thiosemicarbazones and their hybrids showing only antibacterial and antifungal activity in Web of Science (WOS) between 2019 and 2024.

Anahtar Kelimeler

Thiosemicarbazone, Antimicrobial, Antibacterial, Antifungal, Biological activity

Kaynakça

• O. Özbek, C. Berkel, Sensor properties of thiosemicarbazones in different analytical methods, Polyhedron 238 (2023) Article ID 116426 16 pages.
• J. Zhu, G. Teng, D. Li, R. Hou, Y. Xia, Synthesis and antibacterial activity of novel Schiff bases of thiosemicarbazone derivatives with adamantane moiety, Medicinal Chemistry Research 30 (2021) 1534–1540.
• Z. Piri, Z. Moradi–Shoeili, A. Assoud, Ultrasonic assisted synthesis, crystallographic, spectroscopic studies and biological activity of three new Zn(II), Co(II) and Ni(II) thiosemicarbazone complexes as precursors for nano-metal oxides, Inorganica Chim Acta 484 (2019) 338–346.
• S. A. Khan, M. Yusuf, Synthesis, spectral studies and in vitro antibacterial activity of steroidal thiosemicarbazone and their palladium (Pd (II)) complexes, European Journal of Medicinal Chemistry 44 (2009) 2270–2274.
• S. Gupta, N. Singh, T. Khan, S. Joshi, Thiosemicarbazone derivatives of transition metals as multi-target drugs: A review, Results in Chemistry 4 (2022) Article ID 100459 11 pages.
• C. C. Pacca, R. E. Marques, J. W. P. Espindola, G. B. O. O. Filho, A. C. L. Leite, M. M. Teixeira, M. L. Nogueira, Thiosemicarbazones and Phthalyl-Thiazoles compounds exert antiviral activity against yellow fever virus and Saint Louis encephalitis virus, Biomedicine & Pharmacotherapy 87 (2017) 381–387.
• D. Cebotari, J. Buils, O. Garbuz, G. Balan, J. Marrot, V. Guérineau, D. Touboul, M. Haouas, M. Segado-Centelles, C. Bo, A. Gulea, S. Floquet, A new series of bioactive Mo(V)2O2S2-based thiosemicarbazone complexes: Solution and DFT studies, and antifungal and antioxidant activities, Journal of Inorganic Biochemistry 245 (2023) Article ID 112258 14 pages.
• F. Vandresen, H. Falzirolli, S. A. Almeida Batista, A. P. B. da Silva-Giardini, D. N. de Oliveira, R. R. Catharino, A. L. T. G. Ruiz, J. E. de Carvalho, M. A. Foglio, C. C. da Silva, Novel R-(+)-limonene-based thiosemicarbazones and their antitumor activity against human tumor cell lines, European Journal of Medicinal Chemistry 79 (2014) 110–116.
• K. Saeed, M. Rafiq, M. Khalid, A. Hussain, F. Siddique, M. Hanif, S. Hussain, K. Mahmood, N. Ameer, M. M. Ahmed, M. Ali Khan, M. Yaqub, M. Jabeen, Synthesis, characterization, computational assay and anti-inflammatory activity of thiosemicarbazone derivatives: Highly potent and efficacious for COX inhibitors, International Immunopharmacology 126 (2024) Article ID 111259 15 pages.
• S. Umamatheswari, B. Balaji, M. Ramanathan, S. Kabilan, Synthesis, stereochemistry, antimicrobial evaluation and QSAR studies of 2,6-diaryltetrahydropyran-4-one thiosemicarbazones, European Journal of Medicinal Chemistry 46 (2011) 1415–1424.
• M. Alam, M. N. Abser, A. Kumer, M. M. H. Bhuiyan, P. Akter, M. E. Hossain, U. Chakma, Synthesis, characterization, antibacterial activity of thiosemicarbazones derivatives and their computational approaches: Quantum calculation, molecular docking, molecular dynamic, ADMET, QSAR, Heliyon 9 (2023) Article ID e16222 14 pages.
• H. Yildirim, E. Guler, M. Yavuz, N. Ozturk, P. Kose Yaman, E. Subasi, E. Sahin, S. Timur, Ruthenium (II) complexes of thiosemicarbazone: Synthesis, biosensor applications and evaluation as antimicrobial agents, Materials Science and Engineering: C 44 (2014) 1–8.
• N. A. Mohamed, R. R. Mohamed, R. S. Seoudi, Synthesis and characterization of some novel antimicrobial thiosemicarbazone O-carboxymethyl chitosan derivatives, International Journal of Biological Macromolecules 63 (2014) 163–169.
• I. Graur, T. Bespalova, V. Graur, V. Tsapkov, O. Garbuz, E. Melnic, P. Bourosh, A. Gulea, A new thiosemicarbazone and its 3d metal complexes: Synthetic, structural, and antioxidant studies, Journal of Chemical Research 47 (6) (2023) 1-8.
• W. Radchatawedchakoon, W. Sangsuwan, S. Kruanetr, U. Sakee, Synthesis and evaluation of simple naked-eye colorimetric chemosensors for anions based on azo dye-thiosemicarbazones, Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 121 (2014) 306–312.
• S. Masuri, B. Era, F. Pintus, E. Cadoni, M.G. Cabiddu, A. Fais, T. Pivetta, Hydroxylated Coumarin-Based Thiosemicarbazones as Dual Antityrosinase and Antioxidant Agents, International Journal of Molecular Sciences 24 (2023) Article ID 1678 16 pages.
• E. S. Çakmakçı, E. Subaşı, E. Öztürk, A. Şahiner, B. Şen Yüksel, Cobalt(II), nickel(II), palladium(II) and zinc(II) metallothiosemicarbazones: Synthesis, characterization, X-ray structures and biological activity, Inorganica Chimica Acta 551 (2023) Article ID 121462 10 pages.
• N. Sharma, N. Dhingra, H. L. Singh, Design, spectral, antibacterial and in-silico studies of new thiosemicarbazones and semicarbazones derived from symmetrical chalcones, Journal of Molecular Structure 1307 (2024) Article ID 138000 10 pages.
• Diksha, M. Kaur, Megha, Reenu, H. Kaur, V. Yempally, Rhenium (I) tricarbonyl complex with thiosemicarbazone ligand derived from Indole-2-carboxaldehyde: Synthesis, crystal structure, computational investigations, antimicrobial activity, and molecular docking studies, Journal of Molecular Structure 1301 (2024) Article ID 137319 15 pages.
• A. A. Aly, E. M. Abdallah, S. A. Ahmed, M. M. Rabee, O. Fuhr, M. A. A. Ibrahim, H. Ali Alzahrani, B. G. M. Youssif, Synthesis and characterization of new palladium (II) and silver (I) thiosemicarbazone derived by acenaphthenequinone complexes and their antimicrobial activity, Polyhedron 251 (2024) Article ID 116851 11 pages.
• M. Beltrán-Torres, H. Santacruz-Ortega, K. A. López-Gastelum, M. Acosta-Elías, E.F. Velázquez-Contreras, G. Aguirre-Hernández, J. Hernández-Paredes, R. Pérez-González, F. Rocha-Alonzo, A. García-Galaz, R. Sugich-Miranda, Synthesis via microwave irradiation, structural characterization, and antibacterial activities of new complexes of bismuth(III) with thiosemicarbazones, Polyhedron 252 (2024) Article ID 116883 14 pages.
• D. Ziembicka, K. Gobis, M. Szczesio, A. Olczak, E. Augustynowicz-Kopeć, A. Głogowska, I. Korona-Głowniak, K. Bojanowski, Synthesis and Structure–Activity Relationship of 2,6-Disubstituted Thiosemicarbazone Derivatives of Pyridine as Potential Antituberculosis Agents, Materials 16 (2023) Article ID 448 19 pages.
• M. Pitucha, P. Ramos, K. Wojtunik-Kulesza, A. Głogowska, J. Stefańska, D. Kowalczuk, D. Monika, E. Augustynowicz-Kopeć, Thermal analysis, antimicrobial and antioxidant studies of thiosemicarbazone derivatives, Journal of Thermal Analysis and Calorimetry 148 (2023) 4223–4234.
• R. Rusnac, O. Garbuz, Y. Chumakov, V. Tsapkov, C. Hureau, D. Istrati, A. Gulea, Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: N-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide, Inorganics (Basel) 11 (2023) Article ID 408 17 pages.
• J. Swaminathan, P. Anbusrinivasan, A. Vijayalakshmi, Synthesis, geometrical, spectral and antibacterial studies of 4-hydroxy-3-methoxybenzaldehyde thiosemicarbazone by experimental and theoretical investigations, Computational and Theoretical Chemistry 1229 (2023) Article ID 114338 7 pages.
• M. Stojičkov, M. Zlatar, P.P. Mazzeo, A. Bacchi, D. Radovanović, N. Stevanović, M. Jevtović, I. Novaković, K. Anđelković, D. Sladić, B. Čobeljić, M. Gruden, The interplay between spin states, geometries, and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone, Polyhedron 237 (2023) Article ID 116389 10 pages.
• A. Ezzat, M.B.I. Mohamed, A.M. Mahmoud, R.S. Farag, Abdou.S. El-Tabl, A. Ragab, Synthesis, spectral characterization, antimicrobial evaluation and molecular docking studies of new Cu (II), Zn (II) thiosemicarbazone based on sulfonyl isatin, Journal of Molecular Structure 1251 (2022) Article ID 132004 15 pages.
• A. Ragab, Y. A. Ammar, A. Ezzat, A. M. Mahmoud, M. B. I. Mohamed, A. S. El-Tabl, R. S. Farag, Synthesis, characterization, thermal properties, antimicrobial evaluation, ADMET study, and molecular docking simulation of new mono Cu (II) and Zn (II) complexes with 2-oxoindole derivatives, Computers in Biology and Medicine 145 (2022) Article ID 105473 17 pages.
• V. Jevtović, H. Hamoud, S. Al-Zahrani, K. Alenezi, S. Latif, T. Alanazi, F. Abdulaziz, D. Dimić, Synthesis, Crystal Structure, Quantum Chemical Analysis, Electrochemical Behavior, and Antibacterial and Photocatalytic Activity of Co Complex with Pyridoxal-(S-Methyl)-isothiosemicarbazone Ligand, Molecules 27 (2022) Article ID 4809 17 pages.
• A. Y. Alzahrani, Y. A. Ammar, M. Abu-Elghait, M. A. Salem, M. A. Assiri, T. E. Ali, A. Ragab, Development of novel indolin-2-one derivative incorporating thiazole moiety as DHFR and quorum sensing inhibitors: Synthesis, antimicrobial, and antibiofilm activities with molecular modelling study, Bioorganic Chemistry 119 (2022) Article ID 105571 20 pages.
• Ü. M. Koçyiğit, M. Doğan, H. Muğlu, P. Taslimi, B. Tüzün, H. Yakan, H. Bal, E. Güzel, İ. Gülçin, Determination of biological studies and molecular docking calculations of isatin-thiosemicarbazone hybrid compounds, Journal of Molecular Structure 1264 (2022) Article ID 133249 8 pages.
• A. Gaber, M.S. Refat, A. A. M. Belal, I. M. El-deen, N. Hassan, R. Zakaria, M. Alhomrani, A.S. Alamri, W. F. Alsanie, E.M. Saied, New Mononuclear and Binuclear Cu(II), Co(II), Ni(II), and Zn(II) Thiosemicarbazone Complexes with Potential Biological Activity : Antimicrobial and Molecular Docking Study, Molecules 26 (2021) 1–18.
• E. M. Abdalla, S. S. Hassan, H.H. Elganzory, S. A. Aly, H. Alshater, Molecular Docking, DFT Calculations, Effect of High Energetic Ionizing Radiation, and Biological Evaluation of Some Novel Metal (II) Heteroleptic Complexes Bearing the Thiosemicarbazone Ligand, Molecules 26 (2021) Article ID 5851 24 pages.
• G. Kalaiarasi, S. Dharani, S. Rex Jeya Rajkumar, M. Ranjani, V.M. Lynch, R. Prabhakaran, Synthesis, spectral characterization, DNA/BSA binding, antimicrobial and in vitro cytotoxicity of cobalt(III) complexes containing 7-hydroxy-4-oxo-4H-chromene Schiff bases, Inorganica Chimica Acta 515 (2021) Article ID 120060 10 pages.
• C. G. L. Nongpiur, M. M. Ghate, D. K. Tripathi, K. M. Poluri, W. Kaminsky, M. R. Kollipara, Study of versatile coordination modes, antibacterial and radical scavenging activities of arene ruthenium, rhodium and iridium complexes containing fluorenone based thiosemicarbazones, Journal of Organometallic Chemistry 957 (2022) Article ID 122148 13 pages.
• T. A. Nibila, P. P. Soufeena, P. Periyat, K. K. Aravindakshan, Synthesis, structural characterization and biological activities of transition metal complexes derived from 2,4-dihydroxybenzaldehyde n(4)-methyl(phenyl)thiosemicarbazone, Journal of Molecular Structure 1231 (2021) Article ID 129938 10 pages.
• J. Qi, X. Wang, T. Liu, M. Kandawa-Schulz, Y. Wang, X. Zheng, Synthesis, antiproliferative activity and mechanism of copper(II)-thiosemicarbazone complexes as potential anticancer and antimicrobial agents, Journal of Coordination Chemistry 73 (2020) 1208–1221.
• V. H. Pham, T. P. D. Phan, D. C. Phan, B. D. Vu, Synthesis and Bioactivity of Thiosemicarbazones Containing Adamantane Skeletons, Molecules 25 (2020) Article ID 324 14 pages.
• A. Ameryckx, L. Pochet, G. Wang, E. Yildiz, B. E. Saadi, J. Wouters, F. Van Bambeke, R. Frédérick, Pharmacomodulations of the benzoyl-thiosemicarbazide scaffold reveal antimicrobial agents targeting d-alanyl-d-alanine ligase in bacterio, European Journal of Medicinal Chemistry 200 (2020) Article ID 112444 13 pages.
• M. S. Aljahdali, A. A. El-Sherif, Synthesis and Biological Evaluation of Novel Zn(II) and Cd(II) Schiff Base Complexes as Antimicrobial, Antifungal, and Antioxidant Agents, Bioinorganic Chemistry and Applications 2020 (2020) 1–17.
• J. C. L. Almeida, R. S. Amim, C. Pessoa, M. C. S. Lourenço, I. C. Mendes, J. A. Lessa, Bismuth(III) complexes with pyrazineformamide thiosemicarbazones: Investigation on the antimicrobial and cytotoxic effects, Polyhedron 189 (2020) Article ID 114709 7 pages.
• J. Devi, M. Yadav, D. K. Jindal, D. Kumar, Y. Poornachandra, Synthesis, spectroscopic characterization, biological screening and in vitro cytotoxic studies of 4‐methyl‐3‐thiosemicarbazone derived Schiff bases and their Co (II), Ni (II), Cu (II) and Zn (II) complexes, Applied Organometallic Chemistry 33 (2019) 1–23.
• D. Polo-Cerón, Cu(II) and Ni(II) Complexes with New Tridentate NNS Thiosemicarbazones: Synthesis, Characterisation, DNA Interaction, and Antibacterial Activity, Bioinorganic Chemistry and Applications 2019 (2019) 1–14.
• K. N. Aneesrahman, K. Ramaiah, G. Rohini, G. P. Stefy, N. S. P. Bhuvanesh, A. Sreekanth, Synthesis and characterisations of copper(II) complexes of 5-methoxyisatin thiosemicarbazones: Effect of N-terminal substitution on DNA/protein binding and biological activities, Inorganica Chimica Acta 492 (2019) 131–141.
• M. M. Alsharekh, I. I. Althagafi, M. R. Shaaban, T. A. Farghaly, Microwave-assisted and thermal synthesis of nanosized thiazolyl-phenothiazine derivatives and their biological activities, Research on Chemical Intermediates 45 (2019) 127–154.
• G. Munikumari, R. Konakanchi, V. B. Nishtala, G. Ramesh, L. R. Kotha, K. B. Chandrasekhar, C. Ramachandraiah, Palladium(II) complexes of 5-substituted isatin thiosemicarbazones: Synthesis, spectroscopic characterization, biological evaluation and in silico docking studies, Synthetic Communications 49 (2019) 146–158.