Research Article
Year 2025,
Volume: 12 Issue: 2, 121 - 126, 01.05.2025
Abstract
References
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- [5] S. Chhabra and K. Shah, ‘‘The novel scaffold 1, 2, 4-benzothiadiazine-1, 1-dioxide: a review,’’ Medicinal Chemistry Research, vol. 30, pp. 15–30, 2021.
- [6] C. Kamoutsis, M. Fesatidou, A. Petrou, A. Geronikaki, V. Poroikov, M. Ivanov, M. Soković, A. Ćirić, A. Carazo, and P. Mladěnka, ‘‘Triazolo based-thiadiazole derivatives. synthesis, biological evaluation and molecular docking studies,’’ Antibiotics, vol. 10, no. 7, p. 804, 2021.
- [7] F. Hassanzadeh, E. Jafari, F. Shojaei, and H. Sadeghi-Aliabadi, ‘‘Synthesis and cytotoxic activity evaluation of some new 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4-triazole derivatives attached to phthalimide,’’ Research in Pharmaceutical Sciences, vol. 16, no. 6, pp. 634–642, 2021.
- [8] A. M. A. Ouf, H. A. Allam, M. Kamel, F. A. Ragab, and S. A. Abdel-Aziz, ‘‘Design, synthesis, cytotoxic and enzyme inhibitory activities of 1, 3, 4-oxadiazole and 1, 3, 4-thiadiazine hybrids against non-small cell lung cancer,’’ Results in Chemistry, vol. 4, p. 100373, 2022.
- [9] F. Z. Mohammed, Y. W. Rizzk, I. M. El-Deen, E. M. Gad, M. El Behery, and A. R. Mahdy, ‘‘Discovery of 2-amino-4h-1, 3, 4-thiadiazine-5 (6h)-one derivatives and their in vitro antitumor investigation,’’ ChemistrySelect, vol. 7, no. 7, p. e202104333, 2022.
- [10] S. Qureshi, G. Ali, M. Idrees, T. Muhammad, I.-K. Kong, M. Abbas, M. I. A. Shah, S. Ahmad, R. D. Sewell, and S. Ullah, ‘‘Selected thiadiazine-thione derivatives attenuate neuroinflammation in chronic constriction injury induced neuropathy,’’ Frontiers in Molecular Neuroscience, vol. 14, p. 728128, 2021.
- [11] S. Alghamdia and M. Asifb, ‘‘phosphodiesterase-iii, iv, and v inhibitors.’’
- [12] S. Baddi, A. Y. Dang-i, T. Huang, C. Xing, S. Lin, and C.-L. Feng, ‘‘Chirality-influenced antibacterial activity of methylthiazole-and thiadiazole-based supramolecular biocompatible hydrogels,’’ Acta Biomaterialia, vol. 141, pp. 59–69, 2022.
- [13] M. Alshubramy, M. Asem, and M. Abdel-Motaal, ‘‘Efficient synthesis of new fused thiadiazines and their spectroscopic, in silico drug likeness, and adme properties,’’ Russian Journal of Organic Chemistry, vol. 58, no. 4, pp. 619–627, 2022.
- [14] A. Maslat, B. Al-Trad, I. Alameen, M. Al-Talib, H. Tashtoush, and B. Ababneh, ‘‘The effect of two novel substituted thiazole and thiadiazine derivatives on experimental type-1 diabetes mellitus,’’ Jordan Journal of Chemistry (JJC), vol. 19, no. 1, pp. 41–47, 2024.
- [15] A. De, S. Sarkar, and A. Majee, ‘‘Recent advances on heterocyclic compounds with antiviral properties,’’ Chemistry of Heterocyclic Compounds, vol. 57, no. 4, pp. 410–416, 2021.
- [16] T. J. Herald, P. Gadgil, and M. Tilley, ‘‘High-throughput micro plate assays for screening flavonoid content and dpph-scavenging activity in sorghum bran and flour,’’ Journal of the Science of Food and Agriculture, vol. 92, no. 11, pp. 2326–2331, 2012.
- [17] M. Čačić, V. Pavić, M. Molnar, B. Šarkanj, and E. Has-Schon, ‘‘Design and synthesis of some new 1, 3, 4-thiadiazines with coumarin moieties and their antioxidative and antifungal activity,’’ Molecules, vol. 19, no. 1, pp. 1163–1177, 2014.
- [18] M. T. Madigan, J. M. Martinko, J. Parker et al., Brock biology of microorganisms. Prentice hall Upper Saddle River, NJ, 1997, vol. 11.
- [19] G. Guzel Kaya, S. Medaglia, V. Candela-Noguera, M. Á. Tormo-Mas, M. D. Marcos, E. Aznar, H. Deveci, and R. Martínez-Máñez, ‘‘Antibacterial activity of linezolid against gram-negative bacteria: Utilization of ε-poly-l-lysine capped silica xerogel as an activating carrier,’’ Pharmaceutics, vol. 12, no. 11, p. 1126, 2020.
- [20] S. B. Kedare and R. Singh, ‘‘Genesis and development of dpph method of antioxidant assay,’’ Journal of food science and technology, vol. 48, pp. 412–422, 2011.
- [21] H. Amira, F. Benchikh, H. Benabdallah, W. Mamache, S. Amira et al., ‘‘Evaluation of antioxidant activities and total phenolic content of hydro-ethanol extract from phlomis bovei de noé areal parts,’’ Journal of drug delivery and therapeutics, vol. 10, no. 5, pp. 45–48, 2020.
- [22] K. Jakovljević, M. D. Joksović, B. Botta, L. S. Jovanović, E. Avdović, Z. Marković, V. Mihailović, M. Andrić, S. Trifunović, and V. Marković, ‘‘Novel 1, 3, 4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies,’’ Comptes Rendus Chimie, vol. 22, no. 8, pp. 585–598, 2019.
Year 2025,
Volume: 12 Issue: 2, 121 - 126, 01.05.2025
Abstract
In this study, some 1,3,4-thiadiazine derivatives were synthesized by condensation of appropriate acetophenone derivatives and thiosemicarbazides because of their wide range of biological applications. Structures of synthesized compounds characterized by 1H NMR and FTIR techniques and evaluated as potential antibacterial or antioxidant agents. The activities of the compounds against Staphylococcus aureus (S. aureus), Bacillus cereus (B. cereus), Escherichia coli (E. coli), and Salmonella typhimurium (S. typhimurium) were evaluated by the Kirby-Bauer disk diffusion method. From the results, it is clear that the compounds (4) and (5) have stronger activity against Gram-positive bacteria but show no inhibition against Gram-negative bacteria. In addition, the DPPH radical scavenging activity of the compounds was determined by microplate assay with various concentrations of the test compounds. Among the synthesized compounds, (4), (5) and (2) showed the highest interactions. The result showed that the DPPH scavenging activity of compounds also appeared to depend on an increase in concentration. The findings of this work have significance in view of the possibility to design new 1, 3, 4-thiadiazine derivatives with improved potency and activity.
Supporting Institution
Necmettin Erbakan University.
Thanks
The authors would like to acknowledge the support of Necmettin Erbakan University.
References
- [1] M. Dinarvand and M. Spain, ‘‘Identification of bioactive compounds from marine natural products and exploration of structure-activity relationships (sar),’’ Antibiotics, vol. 10, no. 3, p. 337, 2021.
- [2] E. Bentivegna, M. Luciani, L. Arcari, I. Santino, M. Simmaco, and P. Martelletti, ‘‘Reduction of multidrug-resistant (mdr) bacterial infections during the covid-19 pandemic: a retrospective study,’’ International journal of environmental research and public health, vol. 18, no. 3, p. 1003, 2021.
- [3] T. M. Terreni, Marco and M. Pregnolato, ‘‘New antibiotics for multidrug-resistant bacterial strains: latest research developments and future perspectives,’’ Molecules, vol. 26, no. 9, p. 2671, 2021.
- [4] P. C. Jilloju, L. Persoons, S. K. Kurapati, D. Schols, S. De Jonghe, D. Daelemans, and R. R. Vedula, ‘‘Discovery of (±)-3-(1 h-pyrazol-1-yl)-6, 7-dihydro-5 h-[1, 2, 4] triazolo [3, 4-b][1, 3, 4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity,’’ Molecular Diversity, vol. 26, no. 3, pp. 1357–1371, 2022.
- [5] S. Chhabra and K. Shah, ‘‘The novel scaffold 1, 2, 4-benzothiadiazine-1, 1-dioxide: a review,’’ Medicinal Chemistry Research, vol. 30, pp. 15–30, 2021.
- [6] C. Kamoutsis, M. Fesatidou, A. Petrou, A. Geronikaki, V. Poroikov, M. Ivanov, M. Soković, A. Ćirić, A. Carazo, and P. Mladěnka, ‘‘Triazolo based-thiadiazole derivatives. synthesis, biological evaluation and molecular docking studies,’’ Antibiotics, vol. 10, no. 7, p. 804, 2021.
- [7] F. Hassanzadeh, E. Jafari, F. Shojaei, and H. Sadeghi-Aliabadi, ‘‘Synthesis and cytotoxic activity evaluation of some new 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4-triazole derivatives attached to phthalimide,’’ Research in Pharmaceutical Sciences, vol. 16, no. 6, pp. 634–642, 2021.
- [8] A. M. A. Ouf, H. A. Allam, M. Kamel, F. A. Ragab, and S. A. Abdel-Aziz, ‘‘Design, synthesis, cytotoxic and enzyme inhibitory activities of 1, 3, 4-oxadiazole and 1, 3, 4-thiadiazine hybrids against non-small cell lung cancer,’’ Results in Chemistry, vol. 4, p. 100373, 2022.
- [9] F. Z. Mohammed, Y. W. Rizzk, I. M. El-Deen, E. M. Gad, M. El Behery, and A. R. Mahdy, ‘‘Discovery of 2-amino-4h-1, 3, 4-thiadiazine-5 (6h)-one derivatives and their in vitro antitumor investigation,’’ ChemistrySelect, vol. 7, no. 7, p. e202104333, 2022.
- [10] S. Qureshi, G. Ali, M. Idrees, T. Muhammad, I.-K. Kong, M. Abbas, M. I. A. Shah, S. Ahmad, R. D. Sewell, and S. Ullah, ‘‘Selected thiadiazine-thione derivatives attenuate neuroinflammation in chronic constriction injury induced neuropathy,’’ Frontiers in Molecular Neuroscience, vol. 14, p. 728128, 2021.
- [11] S. Alghamdia and M. Asifb, ‘‘phosphodiesterase-iii, iv, and v inhibitors.’’
- [12] S. Baddi, A. Y. Dang-i, T. Huang, C. Xing, S. Lin, and C.-L. Feng, ‘‘Chirality-influenced antibacterial activity of methylthiazole-and thiadiazole-based supramolecular biocompatible hydrogels,’’ Acta Biomaterialia, vol. 141, pp. 59–69, 2022.
- [13] M. Alshubramy, M. Asem, and M. Abdel-Motaal, ‘‘Efficient synthesis of new fused thiadiazines and their spectroscopic, in silico drug likeness, and adme properties,’’ Russian Journal of Organic Chemistry, vol. 58, no. 4, pp. 619–627, 2022.
- [14] A. Maslat, B. Al-Trad, I. Alameen, M. Al-Talib, H. Tashtoush, and B. Ababneh, ‘‘The effect of two novel substituted thiazole and thiadiazine derivatives on experimental type-1 diabetes mellitus,’’ Jordan Journal of Chemistry (JJC), vol. 19, no. 1, pp. 41–47, 2024.
- [15] A. De, S. Sarkar, and A. Majee, ‘‘Recent advances on heterocyclic compounds with antiviral properties,’’ Chemistry of Heterocyclic Compounds, vol. 57, no. 4, pp. 410–416, 2021.
- [16] T. J. Herald, P. Gadgil, and M. Tilley, ‘‘High-throughput micro plate assays for screening flavonoid content and dpph-scavenging activity in sorghum bran and flour,’’ Journal of the Science of Food and Agriculture, vol. 92, no. 11, pp. 2326–2331, 2012.
- [17] M. Čačić, V. Pavić, M. Molnar, B. Šarkanj, and E. Has-Schon, ‘‘Design and synthesis of some new 1, 3, 4-thiadiazines with coumarin moieties and their antioxidative and antifungal activity,’’ Molecules, vol. 19, no. 1, pp. 1163–1177, 2014.
- [18] M. T. Madigan, J. M. Martinko, J. Parker et al., Brock biology of microorganisms. Prentice hall Upper Saddle River, NJ, 1997, vol. 11.
- [19] G. Guzel Kaya, S. Medaglia, V. Candela-Noguera, M. Á. Tormo-Mas, M. D. Marcos, E. Aznar, H. Deveci, and R. Martínez-Máñez, ‘‘Antibacterial activity of linezolid against gram-negative bacteria: Utilization of ε-poly-l-lysine capped silica xerogel as an activating carrier,’’ Pharmaceutics, vol. 12, no. 11, p. 1126, 2020.
- [20] S. B. Kedare and R. Singh, ‘‘Genesis and development of dpph method of antioxidant assay,’’ Journal of food science and technology, vol. 48, pp. 412–422, 2011.
- [21] H. Amira, F. Benchikh, H. Benabdallah, W. Mamache, S. Amira et al., ‘‘Evaluation of antioxidant activities and total phenolic content of hydro-ethanol extract from phlomis bovei de noé areal parts,’’ Journal of drug delivery and therapeutics, vol. 10, no. 5, pp. 45–48, 2020.
- [22] K. Jakovljević, M. D. Joksović, B. Botta, L. S. Jovanović, E. Avdović, Z. Marković, V. Mihailović, M. Andrić, S. Trifunović, and V. Marković, ‘‘Novel 1, 3, 4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies,’’ Comptes Rendus Chimie, vol. 22, no. 8, pp. 585–598, 2019.
There are 22 citations in total.
Details
| Primary Language | English |
|---|---|
| Subjects | Engineering Practice |
| Journal Section | Research Articles |
| Authors | |
| Publication Date | May 1, 2025 |
| Submission Date | July 22, 2024 |
| Acceptance Date | November 25, 2024 |
| Published in Issue | Year 2025 Volume: 12 Issue: 2 |
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