Prospects for the search for new biologically active compounds among the derivatives of the heterocyclic system of 1,2,4-triazole

Year 2022, Volume: 42 Issue: 3, 175 - 186, 01.09.2022

Yurii Sameliuk , Andrii Kaplaushenko , Natalia Nedorezanıuk , Liusine Ostretsova , Feodosiia Diakova , Bogdan Gutyj

https://doi.org/10.52794/hujpharm.1019625

Cited By: 7

Abstract

The purpose of this literature review was to systematize data from studies of the biological activity of 1,2,4-triazole derivatives with substituents in positions 4 and 5. The authors set the task of forming an idea of current directions in the selection of substitutions for 1,2,4-triazole based on research.
As a result of the study, 75 literature sources were analyzed. This made it possible to form a further vector in terms of searching for biologically active structures among 1,2,4-triazole derivatives. The review develops a modern approach to the search for biologically active substances among 1,2,4-triazole derivatives. Sys- tematized data on the nature of substituents in the core of 1,2,4-triazole, which affect a specific type of activity.
The search material was selected over the past decade with the highest number of citations at the time of literature analysis.

Keywords

Biological activity, bibliosemantic method, organic synthesis, 1, 2, 4-triazole

Supporting Institution

Zaporizhzhia State Medical University, Faculty of Pharmacy, Department of physical and colloidal chemistry, Zaporizhzhia, Ukraine

Project Number

2

Thanks

thanks to Hacettepe University Journal of Faculty of Pharmacy

References

• 1. Varynskyi, B., & Kaplaushenko, A. (2020). Metabolism study of morpholinium 2-((4-(2-methoxyphenyl)-5-(pyridin-4-yl)-4-1, 2, 4-triazole-3-yl) thio) acetate. Current Issues in Pharmacy and Medical Sciences, 33(2), 72-75.
• 2. Oliinykov, D., Kaplaushenko, A., Trehub, S., & Kovalyova, K. Manufacture of spherical granules of isosorbide dinitrate with modified release. Journal of Faculty of Pharmacy of Ankara University, 44(3), 481-493.
• 3. Frolova, Y., Kaplaushenko, A., & Nagornaya, N. (2020). Design, synthesis, antimicrobial and antifungal activities of new 1, 2, 4-triazole derivatives containing 1H-tetrazole moiety. Journal of Faculty of Pharmacy of Ankara University, 44(1), 70-88.
• 4. Shcherbyna, R., Parchenko, V., Varynskyi, B., & Kaplaushenko, A. (2019). The development of HPLC-DAD method for determination of active pharmaceutical ingredient in the potassium 2-((4-amino-5-(morpholinomethyl)-4H-1, 2, 4-triazol-3-yl) thio) acetate substance. Current Issues In Pharmacy And Medical Sciences, 32(1), 5-9.
• 5. Varynskyi, B., & Kaplaushenko, A. (2019). The force degradation study of the morpholinium 2-((4-(2-methoxyphenyl)-5-(pyridin-4-YL)-4H-1,2,4-triazol-3-yl) Thio) Acetate. Indonesian Journal of Pharmacy, 30(1), 25.
• 6. Frolova, Y., Kaplaushenko, A., & Nagornaya, N. (2020). Design, synthesis, antimicrobial and antifungal activities of new 1, 2, 4-triazole derivatives containing 1h-tetrazole moiety. Journal of Faculty of Pharmacy of Ankara University, 44(1), 70-88.
• 7. Shcherbyna, R., Parchenko, V., Varynskyi, B., & Kaplaushenko, A. (2019). The development of HPLC-DAD method for determination of active pharmaceutical ingredient in the potassium 2-((4-amino-5-(morpholinomethyl)-4H-1, 2, 4-triazol-3-yl) thio) acetate substance. Current Issues In Pharmacy And Medical Sciences, 32(1), 5-9.
• 8. Varynskyi, B., & Kaplaushenko, A. (2019). The Force Degradation Study of The Morpholinium 2-((4-(2-Methoxyphenyl)-5-(Pyridin-4-YL)-4H-1, 2, 4-Triazol-3-YL) Thio) Acetate. Indonesian Journal of Pharmacy, 30(1), 25.
• 9. Samelyuk, Y. G., & Kaplaushenko, A. G. (2014). Synthesis of 3-alkylthio (sulfo)-1, 2, 4-triazoles, Containing methoxyphenyl substituents at C5atoms, Their antipyretic activity, Propensity to adsorption and acute toxicity. Journal of Chemical and Pharmaceutical Research, 6(5), 1117-1121.
• 10. Varynsky, B. O., Parchenko, V. V., Knysh, E. H., Panasenko, O. Y., & Kaplaushenko, A. H. (2017). Development and validation method for determination of the active ingredient of the drug" a vesstym" in the poultry eggs. Azerbaijan Pharmaceutical and Pharmacotherapy Journal, 17(2), 10-17.
• 11. Joshi, R., Kumari, A., Singh, K., Mishra, H., & Pokharia, S. (2020). Triorganotin (IV) complexes of Schiff base derived from 1, 2, 4-triazole moiety: Synthesis, spectroscopic investigation, DFT studies, antifungal activity and molecular docking studies. Journal of Molecular Structure, 1206, 127639.
• 12. Zoidis, G., Kritsi, E., Lecinska, P., Ivanov, M., Zoumpoulakis, P., Sokovic, M., & Catto, M. (2021). The triazole ring as a privileged scaffold for putative antifungals: Synthesis and evaluation of a series of new analogues. ChemMedChem, 16(1), 134-144.
• 13. Pagniez, F., Lebouvier, N., Na, Y. M., Ourliac-Garnier, I., Picot, C., Le Borgne, M., & Le Pape, P. (2020). Biological exploration of a novel 1, 2, 4-triazole-indole hybrid molecule as antifungal agent. Journal of enzyme inhibition and medicinal chemistry, 35(1), 398-403.
• 14. Venugopala, K. N., Kandeel, M., Pillay, M., Deb, P. K., Abdallah, H. H., Mahomoodally, M. F., & Chopra, D. (2020). Anti-Tubercular Properties of 4-Amino-5-(4-Fluoro-3-Phenoxyphenyl)-4H-1, 2, 4-Triazole-3-Thiol and Its Schiff Bases: Computational Input and Molecular Dynamics. Antibiotics, 9(9), 559.
• 15. Shurygina, I. A., Prozorova, G. F., Trukhan, I. S., Korzhova, S. A., Fadeeva, T. V., Pozdnyakov, A. S., ... & Shurygin, M. G. (2020). Nontoxic silver/poly-1-vinyl-1, 2, 4-triazole nanocomposite materials with antibacterial activity. Nanomaterials, 10(8), 1477.
• 16. Ahuja, R., Sidhu, A., Bala, A., Arora, D., & Sharma, P. (2020). Structure based approach for twin-enzyme targeted benzimidazolyl-1, 2, 4-triazole molecular hybrids as antifungal agents. Arabian Journal of Chemistry, 13(6), 5832-5848.
• 17. Safonov, A. A., & Nevmyvaka, A. V. (2020). A study of antimicrobial and antifungal activity of 2-((5-(2-bromophenyl)-4-substituted-4H-1, 2, 4-triazol-3-yl) thio) acetates.
• 18. Riaz, N., Iftikhar, M., Saleem, M., Hussain, S., Rehmat, F., Afzal, Z., ... & al-Rashida, M. (2020). New synthetic 1, 2, 4-triazole derivatives: Cholinesterase inhibition and molecular docking studies. Results in Chemistry, 2, 100041.
• 19. Ayyash, A. N. (2020, December). A new [1, 2, 4] triazolo [3, 4-B][1, 3, 4] thiadiazepine derivatives: Synthesis and antimicrobial studies. In AIP Conference Proceedings (Vol. 2290, No. 1, p. 030040). AIP Publishing LLC.
• 20. Tratrat, C. (2020). 1, 2, 4-Triazole: A privileged scaffold for the development of potent antifungal agents-a brief review. Current Topics in Medicinal Chemistry, 20(24), 2235-2258.
• 21. Chehrouri, M., Othman, A. A., Moreno-Cabrerizo, C., Gholinejad, M., & Sansano, J. M. (2020). Synthesis of 5-heptadecyl-and 5-heptadec-8-enyl substituted 4-amino-1, 2, 4-triazole-3-thiol and 1, 3, 4-oxadiazole-2-thione from (Z)-octadec-9-enoic acid: preparation of Palladium (II) complexes and evaluation of their antimicrobial activity. Monatshefte für Chemie-Chemical Monthly, 151(2), 173-180.
• 22. Elkanzi, N. A. A., & Hrichi, H. (2020). Design and Evaluation of Antimicrobial Activity of New Pyrazole, 1, 2, 4-Triazole, and 1, 3, 4-Thiadiazol Derivatives Bearing 1, 4-Dihydroquinoxaline Moiety. Russian Journal of Bioorganic Chemistry, 46(5), 715-725.
• 23. Guzeldemirci, N. U., Satana, D., & Kucukbasmaci, O. (2020). Synthesis and antimicrobial activity evaluation of new hydrazide-hydrazones derived from 1, 2, 4-triazole. Journal of the Faculty of Pharmacy of Istanbul University, 50(1), 49-54.
• 24. Venugopala, K. N., Kandeel, M., Pillay, M., Deb, P. K., Abdallah, H. H., Mahomoodally, M. F., & Chopra, D. (2020). Anti-Tubercular Properties of 4-Amino-5-(4-Fluoro-3-Phenoxyphenyl)-4H-1, 2, 4-Triazole-3-Thiol and Its Schiff Bases: Computational Input and Molecular Dynamics. Antibiotics, 9(9), 559.
• 25. Beyzaei, H., Kudeyani, M. G., Delarami, H. S., & Aryan, R. (2020). Synthesis, antimicrobial and antioxidant evaluation, and molecular docking study of 4, 5-disubstituted 1, 2, 4-triazole-3-thiones. Journal of Molecular Structure, 1215, 128273.
• 26. Verma, D., Sharma, S., Sahni, T., & Arora, G. (2020). Green Tamarind Extract Catalyzed Synthesis of 4-Amino-1, 2, 4-Triazole Derivatives and Their In-vitro Antimicrobial Activity. International Research Journal of Pure and Applied Chemistry, 44-56.
• 27. Wu, S., Qi, L., Ren, Y., & Ma, H. (2020). 1, 2, 4-triazole-3-thione Schiff bases compounds: Crystal structure, hirshfeld surface analysis, DFT studies and biological evaluation. Journal of Molecular Structure, 1219, 128591.
• 28. Dincel, E. D., Ulusoy‐Güzeldemirci, N., Şatana, D., & Küçükbasmacı, Ö. (2021). Design, synthesis, characterization and antimicrobial evaluation of some novel hydrazinecarbothioamide, 4‐thiazolidinone and 1, 2, 4‐triazole‐3‐thione derivatives. Journal of Heterocyclic Chemistry, 58(1), 195-205.
• 29. Brahimi, F. T., Belkhadem, F., Trari, B., & Othman, A. A. (2020). Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity. Grasas y Aceites, 71(4), 378.
• 30. Yildirim, N. (2020). Synthesis of Novel 3-(4-tert-Butylphenyl)-5-Cylopropyl-4H-1, 2, 4-Triazole Derivatives with Antioxidative and Antimicrobial Activities. Letters in Drug Design & Discovery, 17(8), 954-964.
• 31. Ghanaat, J., Khalilzadeh, M. A., Zareyee, D., Shokouhimehr, M., & Varma, R. S. (2020). Cell cycle inhibition, apoptosis, and molecular docking studies of the novel anticancer bioactive 1, 2, 4-triazole derivatives. Structural Chemistry, 31(2), 691-699.
• 32. Turky, A., Sherbiny, F. F., Bayoumi, A. H., Ahmed, H. E., & Abulkhair, H. S. (2020). Novel 1, 2, 4‐triazole derivatives: Design, synthesis, anticancer evaluation, molecular docking, and pharmacokinetic profiling studies. Archiv der Pharmazie, 353(12), 2000170.
• 33. Kumar, V. (2021). In silico characterization, molecular docking, and in vitro evaluation of triazole derivatives as potential anticancer agents. Asian Journal of Pharmaceutical and Clinical Research, 22-28.
• 34. Gomha, S. M., Muhammad, Z. A., Ezz El-Arab, E., Elmetwally, A. M., El-Sayed, A. A., & Matar, I. K. (2020). Design, Synthesis, Molecular Docking Study and Anti-Hepatocellular Carcinoma Evaluation of New Bis-Triazolothiadiazines. Mini reviews in medicinal chemistry, 20(9), 788-800.
• 35. Al-Hussain, S. A., Farghaly, T. A., Zaki, M. E., Abdulwahab, H. G., Al-Qurashi, N. T., & Muhammad, Z. A. (2020). Discovery of novel indolyl-1, 2, 4-triazole hybrids as potent vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitors with potential anti-renal cancer activity. Bioorganic Chemistry, 105, 104330.
• 36. Turky, A., Bayoumi, A. H., Sherbiny, F. F., El-Adl, K., & Abulkhair, H. S. (2021). Unravelling the anticancer potency of 1, 2, 4-triazole-N-arylamide hybrids through inhibition of STAT3: synthesis and in silico mechanistic studies. Molecular Diversity, 25(1), 403-420.
• 37. Aouad, M. R., Al-Mohammadi, H. M., Al-Blewi, F. F., Ihmaid, S., Elbadawy, H. M., Althagfan, S. S., & Rezki, N. (2020). Introducing of acyclonucleoside analogues tethered 1, 2, 4-triazole as anticancer agents with dual epidermal growth factor receptor kinase and microtubule inhibitors. Bioorganic chemistry, 94, 103446.
• 38. Patel, K. R., Brahmbhatt, J. G., Pandya, P. A., Daraji, D. G., Patel, H. D., Rawal, R. M., & Baran, S. K. (2021). Design, synthesis and biological evaluation of novel 5-(4-chlorophenyl)-4-phenyl-4H-1, 2, 4-triazole-3-thiols as an anticancer agent. Journal of Molecular Structure, 1231, 130000.
• 39. Gomaa, H. A., El-Sherief, H. A., Hussein, S., Gouda, A. M., Salem, O. I., Alharbi, K. S., ... & Youssif, B. G. (2020). Novel 1, 2, 4-triazole derivatives as apoptotic inducers targeting p53: Synthesis and antiproliferative activity. Bioorganic Chemistry, 105, 104369.
• 40. Khan, B., Naiyer, A., Athar, F., Ali, S., & Thakur, S. C. (2021). Synthesis, characterization and anti-inflammatory activity evaluation of 1, 2, 4-triazole and its derivatives as a potential scaffold for the synthesis of drugs against prostaglandin-endoperoxide synthase. Journal of Biomolecular Structure and Dynamics, 39(2), 457-475.
• 41. Beyzaei, H., Kudeyani, M. G., Delarami, H. S., & Aryan, R. (2020). Synthesis, antimicrobial and antioxidant evaluation, and molecular docking study of 4, 5-disubstituted 1, 2, 4-triazole-3-thiones. Journal of Molecular Structure, 1215, 128273.
• 42. Khokhar, D., Jadoun, S., Arif, R., Jabin, S., & Budhiraja, V. (2021). Copolymerization of o-phenylenediamine and 3-Amino-5-methylthio-1H-1, 2, 4-triazole for tuned optoelectronic properties and its antioxidant studies. Journal of Molecular Structure, 1228, 129738.
• 43. Geetha, B. M., Brinda, K. N., Achar, G., Małecki, J. G., Alwarsamy, M., Betageri, V. S., & Budagumpi, S. (2020). Coumarin incorporated 1, 2, 4–triazole derived silver (I) N–heterocyclic carbene complexes as efficient antioxidant and antihaemolytic agents. Journal of Molecular Liquids, 301, 112352.
• 44. Brahimi, F. T., Belkhadem, F., Trari, B., & Othman, A. A. (2020). Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity. Grasas y Aceites, 71(4), 378.
• 45. Ihnatova, T., Kaplaushenko, A., Frolova, Y., & Pryhlo, E. (2021). Synthesis and antioxidant properties of some new 5-phenethyl-3-thio-1, 2, 4-triazoles. Pharmacia, 68, 129-133.
• 46. Zykova, S. S., Talismanov, V. S., Tsaplin, G. V., Bulatov, I. P., Popkov, S. V., Karmanova, O. G., & Savinkov, A. V. (2019). Study of acute toxicity and antihypoxic activity of N4-substituted 5-(1, 2, 4-triazole-1-ylmethyl)-1, 2, 4-triazole-3-thiones. International Journal of Pharmaceutical Research, 11(3), 1189-1192.
• 47. Kravchenko, T. V., Panasenko, O. I., & Knysh, E. G. (2016). Biological activity of the derivatives of 1, 2, 4-triazole. Farmatsevtychnyi zhurnal, (5), 25-30.
• 48. Odyntsova V. M., Knysh Ye. G., & Panasenko O. I. (2018). Syntesis, physical and chemical properties, antihypoxic activity of some 5-[((5-(adamantane-1-yl)- 4-R-4H-1,2,4-triazole-3-yl)thio)methyl]-N-R1-1,3,4-thiadiazole-2-amines and 5-[((5-(adamantane-1-yl)- 4-R-4H-1,2,4-triazole-3-yl)thio)methyl]-4-R1-4H-1,2,4-triazole-3-thiols. Current issues in pharmacy and medicine: science and practice, 11(1), 17-22.
• 49. Kucheryavyi, Y. M., Kaplaushenko, A. G., & Korzhova, A. S. (2014). Synthesis of 5-R-4-R1-3-alkylthio-1, 2, 4-triazoles and study influence of their adsorption ability on the results of toxicity and anti-hypoxic activity. The Pharma Innovation, 3(1, Part A), 69.
• 50. Odyntsova, V. M., & Pruglo, Y. S. (2015). Synthesis, physical-chemical properties and the study of anti-hypoxemic activity of 5-(adamantane-1-yl)-4-R-1, 2, 4-triazole-3-thion alkylderivatives.
• 51. Shcherbyna, R., & Vashchyk, Y. (2019). The research of 1, 2, 4-triazole derivatives hepatoprotective activity under tetracycline and infectious hepatitis. Ankara Üniversitesi Eczacılık Fakültesi Dergisi, 43(2), 135-146.
• 52. Shcherbyna, R. O., Samura, Т. О., Kyrychko, B. P., Zvenihorodska, Т. V., & Hyrenko, I. V. (2017). The research of ammonium 2-((4-amino-5-(morpholinomethyl)-4H-1, 2, 4-triazole-3-yl) thio) acetate (PKR-177) influence on biochemical indices in rats blood under hepatitis initiated by tetrachloride methane. Запорожский медицинский журнал, (19, № 6), 819-822.
• 53. Rud, A. M., Kaplaushenko, A. G., Pruglo, Y. S., Sameliuk, Y. G., & Frolova, Y. S. (2018). Hepatoprotective activity of 1,2,4-triazole-3-thione derivatives, which contains on C5 atomic carbon hydroxy(phenyl)methyl dependent. Ukrainian biopharmaceutical journal, (3 (56)), 10-15.
• 54. Shi, Y., Wang, Q., Rong, J., Ren, J., Song, X., Fan, X., ... & Yu, L. (2019). Synthesis and biological evaluation of (1, 2, 4) triazole [4, 3-a] pyridine derivatives as potential therapeutic agents for concanavalin A-induced hepatitis. European journal of medicinal chemistry, 179, 182-195.
• 55. Goher, S. S., Griffett, K., Hegazy, L., Elagawany, M., Arief, M. M., Avdagic, A., ... & Elgendy, B. (2019). Development of novel liver X receptor modulators based on a 1, 2, 4-triazole scaffold. Bioorganic & medicinal chemistry letters, 29(3), 449-453.
• 56. Liao, L., Jiang, C., Chen, J., Shi, J., Li, X., Wang, Y., ... & Zhang, J. (2020). Synthesis and biological evaluation of 1, 2, 4-triazole derivatives as potential neuroprotectant against ischemic brain injury. European journal of medicinal chemistry, 190, 112114.
• 57. Ramaiah, M. J., Karthikeyan, D., Mathavan, S., Yamajala, R. B., Ramachandran, S., Vasavi, P. J., & Chandana, N. V. (2020). Synthesis, in vitro and structural aspects of benzothiazole analogs as anti-oxidants and potential neuroprotective agents. Environmental Toxicology and Pharmacology, 79, 103415.
• 58. Li, W., Yang, X., Song, Q., Cao, Z., Shi, Y., Deng, Y., & Zhang, L. (2020). Pyridoxine-resveratrol hybrids as novel inhibitors of Mao-B with antioxidant and neuroprotective activities for the treatment of parkinson’s disease. Bioorganic chemistry, 97, 103707.
• 59. Sarojini, B. K., Manjulaa, P. S., & Rajc, C. G. D. (2015). In vivo neuroprotection study of two 1, 2, 4-triazole derivatives in Drosophila melanogaster Oregon K flies. Journal of Pharmacy Research, 9(6), 351-358.
• 60. Xu, M., Peng, Y., Zhu, L., Wang, S., Ji, J., & Rakesh, K. P. (2019). Triazole derivatives as inhibitors of Alzheimer's disease: Current developments and structure-activity relationships. European journal of medicinal chemistry, 180, 656-672.
• 61. Safonov, A. and Nevmyvaka, A., 2020. Actoprotective activity research of 2-((5-(2-bromophenyl)-4-substituted-4H-1,2,4-triazole-3-yl)thio)acetates. Current issues in pharmacy and medicine: science and practice, 13(2(33), pp.260-264.
• 62. Bihdan, O. A. (2020). Actoprotective activity of some 5-(thiophen-3-ylmethyl)-4-R1-1, 2, 4-triazole-3-thiols derivatives. Farmatsevtychnyi zhurnal, (3), 80-85.
• 63. Danilchenko, D. M., & Safonov, А. А. (2017). Diuretic activity of 2-((4-amino-5-R-4H-1, 2, 4-triazole-3-yl) thio) acetohydrazides. Запорожский медицинский журнал, (19,№ 4), 517-519.
• 64. Kucheryavyi, Y. N., Kaplaushenko, A. G., & Pruhlo, E. S. (2014). Synthesis and diuretic activity of 2-(5-(phenoxymethyl)-4-r1-1, 2, 4-triazole-3-ylthio) acetic acids and their salts. Запорожский медицинский журнал, (6), 101-104.
• 65. Kravchenko, T., 2018. The search for new 4-amino-5-methyl-4H-1,2,4-triasole-3-thion derivatives with diuretic activity. Zaporozhye Medical Journal, 20(3), pp.421-424.
• 66. Muzaffar, S., Shahid, W., Riaz, N., Saleem, M., Ashraf, M., Bashir, B., ... & Gross, H. (2021). Probing phenylcarbamoylazinane-1, 2, 4-triazole amides derivatives as lipoxygenase inhibitors along with cytotoxic, ADME and molecular docking studies. Bioorganic Chemistry, 107, 104525.
• 67. Nawaz, S., Shareef, M., Shahid, H., Mushtaq, M., & Sarfraz, M. (2017). A review of antihyperlipidemic effect of synthetic phenolic compounds. Matrix Science Medica, 1(1), 22-26.
• 68. Kholodnyak, S. V., Schabelnyk, K. P., Shernova, G. A., Sergeieva, T. Y., Ivchuk, V. V., Voskoboynik, O. Y., ... & Shishkina, S. V. (2015). Hydrolytic cleavage of the pyrimidine ring in 2-aryl-[1, 2, 4] triazole [1, 5-c] quinazolines: physico-chemical properties and the hypoglycemic activity of the compounds synthesized. News of Pharmacy, (3 (83)), 9-17.
• 69. Brahimi, F. T., Belkhadem, F., Trari, B., & Othman, A. A. (2020). Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity. Grasas y Aceites, 71(4), 378.
• 70. Menteşe, E., Baltaş, N., & Bekircan, O. (2019). Synthesis and kinetics studies of N′‐(2‐(3, 5‐disubstituted‐4H‐1, 2, 4‐triazol‐4‐yl) acetyl)‐6/7/8‐substituted‐2‐oxo‐2H‐chromen‐3‐carbohydrazide derivatives as potent antidiabetic agents. Archiv der Pharmazie, 352(12), 1900227.
• 71. Goher, S. S., Griffett, K., Hegazy, L., Elagawany, M., Arief, M. M., Avdagic, A., ... & Elgendy, B. (2019). Development of novel liver X receptor modulators based on a 1, 2, 4-triazole scaffold. Bioorganic & medicinal chemistry letters, 29(3), 449-453.
• 72. Kaproń, B., Łuszczki, J., Paneth, A., Wujec, M., Siwek, A., Karcz, T., ... & Plech, T. (2017). Molecular mechanism of action and safety of 5-(3-chlorophenyl)-4-hexyl-2, 4-dihydro-3H-1, 2, 4-triazole-3-thione-a novel anticonvulsant drug candidate. International journal of medical sciences, 14(8), 741.
• 73. Ghaleb, A., Aouidate, A., Ghamali, M., Sbai, A., Bouachrine, M., & Lakhlifi, T. (2017). 3D-QSAR Modeling and Molecular Docking Studies on a Series of 1, 2, 4 Triazole Containing Diarylpyrazolyl Carboxamide as CB1 Cannabinoid Receptor Ligand. International Research Journal of Pure and Applied Chemistry, 1-13.
• 74. Kaproń, B., Łuszczki, J. J., Płazińska, A., Siwek, A., Karcz, T., Gryboś, A., ... & Plech, T. (2019). Development of the 1, 2, 4-triazole-based anticonvulsant drug candidates acting on the voltage-gated sodium channels. Insights from in-vivo, in-vitro, and in-silico studies. European Journal of Pharmaceutical Sciences, 129, 42-57.
• 75. Mioc, M., Avram, S., Tomescu, A. B., Chiriac, D. V., Heghes, A., Voicu, M., ... & Kurunczi, L. (2017). Docking Study of 3-mercapto-1, 2, 4-triazole derivatives as inhibitors for VEGFR and EGFR. Rev. Chim, 4-7.