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

Yıl 2022, Cilt: 42 Sayı: 3, 175 - 186, 01.09.2022
https://doi.org/10.52794/hujpharm.1019625

Öz

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.

Destekleyen Kurum

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

Proje Numarası

2

Teşekkür

thanks to Hacettepe University Journal of Faculty of Pharmacy

Kaynakça

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

Yıl 2022, Cilt: 42 Sayı: 3, 175 - 186, 01.09.2022
https://doi.org/10.52794/hujpharm.1019625

Öz

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.

Proje Numarası

2

Kaynakça

  • 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.
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  • 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.
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  • 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.
Toplam 75 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Eczacılık ve İlaç Bilimleri
Bölüm Review Articles
Yazarlar

Yurii Sameliuk

Andrii Kaplaushenko 0000-0001-8675-5081

Natalia Nedorezanıuk

Liusine Ostretsova

Feodosiia Diakova 0000-0003-3132-3497

Bogdan Gutyj 0000-0002-5971-8776

Proje Numarası 2
Yayımlanma Tarihi 1 Eylül 2022
Kabul Tarihi 30 Mart 2022
Yayımlandığı Sayı Yıl 2022 Cilt: 42 Sayı: 3

Kaynak Göster

Vancouver Sameliuk Y, Kaplaushenko A, Nedorezanıuk N, Ostretsova L, Diakova F, Gutyj B. Prospects for the search for new biologically active compounds among the derivatives of the heterocyclic system of 1,2,4-triazole. HUJPHARM. 2022;42(3):175-86.