Research Article
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BAZI 1,2,4-TRİAZOL YOĞUNLAŞTIRILMIŞ TÜREVLERİNİN SENTEZİ, ÖZELLİKLERI VE BİYOLOJİK POTANSİYELİ

Year 2022, , 308 - 321, 29.05.2022
https://doi.org/10.33483/jfpau.971602

Abstract

Amaç: Çalışmanın amacı 1,2,4-triazol, indol ve pirol içeren biyolojik olarak aktif heterosiklik sistemlerin sentezi için etkili yöntemler geliştirmektir. Bu çalısmada, öncelikle çalısma için gerekli olan on üç adet [1,2,4]triazolo[3,4-b][1,3,4]tiadiazol bilesigi sentezlenmistir.
Gereç ve Yönetim: Sentezlenen bileşiklerin kimyasal yapıları elementel analiz, 1H NMR, LC-MS teknikleri ile karakterize edildi. Sentezlenen maddelerin biyolojik potansiyelleri, moleküler yerleştirme yöntemi ile tahmin edildi.
Sonuç ve Tartışma: [1,2,4]triazolo[3,4-b][1,3,4]tiadiazollerin sentezi için optimal bir yöntem geliştirildi. Moleküler modelleme çalışmalarında, bileşiklerin bazı açılardan bilinen ilaçlara benzer olduğu bulunmuştur. Ayrıca her bir molekülün siklooksijenaz-1, lanosterol 14-α-demetilaz ve anaplastik lenfoma kinazların kristal yapılarındaki aktif bölgeler ile etkileşimi in siliko olarak değerlendirildi.

References

  • 1. Zaher, N. H., Mostafa, M. I., & Altaher, A. Y. (2020). Design, synthesis and molecular docking of novel triazole derivatives as potential CoV helicase inhibitors. Acta Pharmaceutica, 70(2), 145-159. doi:10.2478/acph-2020-0024.
  • 2. Özil, M., Tacal, G., Baltaş, N., Emirik, M. (2020). Synthesis and Molecular Docking Studies of Novel Triazole Derivatives as Antioxidant Agents. Letters in Organic Chemistry, 17(4), 309-320.
  • 3. Vanjare, B. D., Mahajan, P. G., Dige, N. C., Raza, H., Hassan, M., Han, Y., Lee, K. H. (2020). Novel 1,2,4-triazole analogues as mushroom tyrosinase inhibitors: synthesis, kinetic mechanism, cytotoxicity and computational studies. Molecular Diversity. https://doi.org/10.1007/s11030-020-10102-5
  • 4. Aggarwal, R., Sumran, G. (2020). An insight on medicinal attributes of 1,2,4-triazoles. European journal of medicinal chemistry, 112652. doi: 10.1016/j.ejmech.2020. 112652.
  • 5. Sonawane, A. D., Rode, N. D., Nawale, L., Joshi, R. R., Joshi, R. A., Likhite, A. P., & Sarkar, D. (2017). Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents. Chemical Biology & Drug Design, 90(2), 200-209. doi: 10.1111/cbdd.12939
  • 6. Гоцуля, Т. С., Панасенко, О. І., Книш, Є. Г., Ачкасова, О. М. (2011). Дослідження антимікробної та протигрибкової активності серед галогенідів 1-алкіл-4-(5-нітрофуран-2-іл)метиленаміно-4Н-1,2,4-тріазолу та їх диметильних аналогів. Запорожский медицинский журнал, 13(5), 140-142.
  • 7. Mioc, M., Avram, S., Bercean, V., Kurunczi, L., Ghiulai, R. M., Oprean, C., … Soica, C. (2018). Design, synthesis and biological activity evaluation of S-substituted 1H-5-mercapto-1,2,4-triazole derivatives as antiproliferative agents in colorectal cancer. Frontiers in Chemistry, 6. doi: 10.3389/fchem.2018.00373
  • 8. Hotsulia, A. S., Fedotov, S. O. (2020). Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives Current issues in pharmacy and medicine: science and practice, 13(2), 182-186.
  • 9. Karpun, Ye. O., Karpenko, Yu. V., Parchenko, M. V., Bihdan, O. A. (2020). Molecular docking and bioavailability of S-alkylderivatives 5-(3-fluorophenyl)-, 5-(5-bromofuran-2-yl)- and -(((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl))thio)methyl)-4-methyl-4H-1,2,4-triazole in silico methods. Current issues in pharmacy and medicine: science and practice, 13(1), 38-45.
  • 10. Funt, L. D., Tomashenko, O. A., Khlebnikov, A. F., Novikov, M. S., & Ivanov, A. Y. (2016). Synthesis, transformations of pyrrolee- and 1,2,4-triazole-containing ensembles, and generation of pyrrolee-substituted triazole NHC. The Journal of Organic Chemistry, 81(22), 11210–11221. doi: 10.1021/acs.joc.6b02200
  • 11. Roman, G. (2019). Schiff bases and triazolothiadiazines derived from a thiophene-substituted 4-amino-3-mercapto-1,2,4-triazole, Acta Chemica Iasi, 27(2), 137-154. doi: 10.2478/achi-2019-0011
  • 12. Ghanaat, J., Khalilzadeh, M. A., & Zareyee, D. (2020). Molecular docking studies, biological evaluation and synthesis of novel 3-mercapto-1,2,4-triazole derivatives. Molecular Diversity. doi:10.1007/s11030-020-10050-0.
  • 13. Mohammed, H. H. H., Abdelhafez, E.-S. M. N., Abbas, S. H., Moustafa, G. A. I., Hauk, G., Berger, J. M., … Abuo-Rahma, G. E.-D. A. (2019). Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity. Bioorganic Chemistry, 102952.
  • 14. Hotsulia, A. S., Fedotov, S. O. (2019). Synthesis, structure and properties of N-R-2-(5-(5-methyl-1H-pyrazole-3-yl)-4-phenyl-4H-1,2,4-triazole-3-ylthio)acetamides. Current issues in pharmacy and medicine: science and practice, 12(1), 4-9.
  • 15. Гоцуля, А. С., Верба, Д. П., Панасенко, О. І., Книш, Є. Г. (2017). Синтез та дослідження властивостей похідних 4-феніл-5-(1Н-пірол-2-іл)-4Н-1,2,4-триазол-3-тіолів. Фармацевтичний журнал, 1, 59-66.

SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE

Year 2022, , 308 - 321, 29.05.2022
https://doi.org/10.33483/jfpau.971602

Abstract

Objective: The aim of the work was to develop effective methods for the synthesis of biologically active heterocyclic systems containing pyrrole, indole and 1,2,4-triazole. In this study, firstly fourteen [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles compounds requiring for this study were synthesized.
Material and Method: Chemical structures of synthesized compounds were characterized with elemental analysis, 1H NMR, LC-MS techniques. The biological potential of the synthesized substances was estimated by the molecular docking method.
Result and Discussion: An optimal method for the synthesis of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles has been developed. In molecular modeling studies, the compounds were found to be similar to known drugs in some respects. Besides, the interaction of each molecule in the active site of the crystal structures of cyclooxygenase-1, lanosterol 14-α-demethylase, kinases of anaplastic lymphoma were considered as in silico.

References

  • 1. Zaher, N. H., Mostafa, M. I., & Altaher, A. Y. (2020). Design, synthesis and molecular docking of novel triazole derivatives as potential CoV helicase inhibitors. Acta Pharmaceutica, 70(2), 145-159. doi:10.2478/acph-2020-0024.
  • 2. Özil, M., Tacal, G., Baltaş, N., Emirik, M. (2020). Synthesis and Molecular Docking Studies of Novel Triazole Derivatives as Antioxidant Agents. Letters in Organic Chemistry, 17(4), 309-320.
  • 3. Vanjare, B. D., Mahajan, P. G., Dige, N. C., Raza, H., Hassan, M., Han, Y., Lee, K. H. (2020). Novel 1,2,4-triazole analogues as mushroom tyrosinase inhibitors: synthesis, kinetic mechanism, cytotoxicity and computational studies. Molecular Diversity. https://doi.org/10.1007/s11030-020-10102-5
  • 4. Aggarwal, R., Sumran, G. (2020). An insight on medicinal attributes of 1,2,4-triazoles. European journal of medicinal chemistry, 112652. doi: 10.1016/j.ejmech.2020. 112652.
  • 5. Sonawane, A. D., Rode, N. D., Nawale, L., Joshi, R. R., Joshi, R. A., Likhite, A. P., & Sarkar, D. (2017). Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents. Chemical Biology & Drug Design, 90(2), 200-209. doi: 10.1111/cbdd.12939
  • 6. Гоцуля, Т. С., Панасенко, О. І., Книш, Є. Г., Ачкасова, О. М. (2011). Дослідження антимікробної та протигрибкової активності серед галогенідів 1-алкіл-4-(5-нітрофуран-2-іл)метиленаміно-4Н-1,2,4-тріазолу та їх диметильних аналогів. Запорожский медицинский журнал, 13(5), 140-142.
  • 7. Mioc, M., Avram, S., Bercean, V., Kurunczi, L., Ghiulai, R. M., Oprean, C., … Soica, C. (2018). Design, synthesis and biological activity evaluation of S-substituted 1H-5-mercapto-1,2,4-triazole derivatives as antiproliferative agents in colorectal cancer. Frontiers in Chemistry, 6. doi: 10.3389/fchem.2018.00373
  • 8. Hotsulia, A. S., Fedotov, S. O. (2020). Synthesis and properties of 5-(((5-amino-1,3,4-thiadiazole-2-yl)thio)methyl)-4-phenyl-1,2,4-triazole-3-thione and its some S-derivatives Current issues in pharmacy and medicine: science and practice, 13(2), 182-186.
  • 9. Karpun, Ye. O., Karpenko, Yu. V., Parchenko, M. V., Bihdan, O. A. (2020). Molecular docking and bioavailability of S-alkylderivatives 5-(3-fluorophenyl)-, 5-(5-bromofuran-2-yl)- and -(((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl))thio)methyl)-4-methyl-4H-1,2,4-triazole in silico methods. Current issues in pharmacy and medicine: science and practice, 13(1), 38-45.
  • 10. Funt, L. D., Tomashenko, O. A., Khlebnikov, A. F., Novikov, M. S., & Ivanov, A. Y. (2016). Synthesis, transformations of pyrrolee- and 1,2,4-triazole-containing ensembles, and generation of pyrrolee-substituted triazole NHC. The Journal of Organic Chemistry, 81(22), 11210–11221. doi: 10.1021/acs.joc.6b02200
  • 11. Roman, G. (2019). Schiff bases and triazolothiadiazines derived from a thiophene-substituted 4-amino-3-mercapto-1,2,4-triazole, Acta Chemica Iasi, 27(2), 137-154. doi: 10.2478/achi-2019-0011
  • 12. Ghanaat, J., Khalilzadeh, M. A., & Zareyee, D. (2020). Molecular docking studies, biological evaluation and synthesis of novel 3-mercapto-1,2,4-triazole derivatives. Molecular Diversity. doi:10.1007/s11030-020-10050-0.
  • 13. Mohammed, H. H. H., Abdelhafez, E.-S. M. N., Abbas, S. H., Moustafa, G. A. I., Hauk, G., Berger, J. M., … Abuo-Rahma, G. E.-D. A. (2019). Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity. Bioorganic Chemistry, 102952.
  • 14. Hotsulia, A. S., Fedotov, S. O. (2019). Synthesis, structure and properties of N-R-2-(5-(5-methyl-1H-pyrazole-3-yl)-4-phenyl-4H-1,2,4-triazole-3-ylthio)acetamides. Current issues in pharmacy and medicine: science and practice, 12(1), 4-9.
  • 15. Гоцуля, А. С., Верба, Д. П., Панасенко, О. І., Книш, Є. Г. (2017). Синтез та дослідження властивостей похідних 4-феніл-5-(1Н-пірол-2-іл)-4Н-1,2,4-триазол-3-тіолів. Фармацевтичний журнал, 1, 59-66.
There are 15 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Research Article
Authors

Andrey Gotsulya 0000-0001-9696-221X

Tetiana Brytanova This is me 0000-0003-1805-4552

Publication Date May 29, 2022
Submission Date July 15, 2021
Acceptance Date January 29, 2022
Published in Issue Year 2022

Cite

APA Gotsulya, A., & Brytanova, T. (2022). SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE. Journal of Faculty of Pharmacy of Ankara University, 46(2), 308-321. https://doi.org/10.33483/jfpau.971602
AMA Gotsulya A, Brytanova T. SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE. Ankara Ecz. Fak. Derg. May 2022;46(2):308-321. doi:10.33483/jfpau.971602
Chicago Gotsulya, Andrey, and Tetiana Brytanova. “SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE”. Journal of Faculty of Pharmacy of Ankara University 46, no. 2 (May 2022): 308-21. https://doi.org/10.33483/jfpau.971602.
EndNote Gotsulya A, Brytanova T (May 1, 2022) SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE. Journal of Faculty of Pharmacy of Ankara University 46 2 308–321.
IEEE A. Gotsulya and T. Brytanova, “SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE”, Ankara Ecz. Fak. Derg., vol. 46, no. 2, pp. 308–321, 2022, doi: 10.33483/jfpau.971602.
ISNAD Gotsulya, Andrey - Brytanova, Tetiana. “SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE”. Journal of Faculty of Pharmacy of Ankara University 46/2 (May 2022), 308-321. https://doi.org/10.33483/jfpau.971602.
JAMA Gotsulya A, Brytanova T. SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE. Ankara Ecz. Fak. Derg. 2022;46:308–321.
MLA Gotsulya, Andrey and Tetiana Brytanova. “SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE”. Journal of Faculty of Pharmacy of Ankara University, vol. 46, no. 2, 2022, pp. 308-21, doi:10.33483/jfpau.971602.
Vancouver Gotsulya A, Brytanova T. SYNTHESIS, PROPERTIES AND BIOLOGICAL POTENTIAL SOME CONDENSED DERIVATIVES 1,2,4-TRIAZOLE. Ankara Ecz. Fak. Derg. 2022;46(2):308-21.

Kapsam ve Amaç

Ankara Üniversitesi Eczacılık Fakültesi Dergisi, açık erişim, hakemli bir dergi olup Türkçe veya İngilizce olarak farmasötik bilimler alanındaki önemli gelişmeleri içeren orijinal araştırmalar, derlemeler ve kısa bildiriler için uluslararası bir yayım ortamıdır. Bilimsel toplantılarda sunulan bildiriler supleman özel sayısı olarak dergide yayımlanabilir. Ayrıca, tüm farmasötik alandaki gelecek ve önceki ulusal ve uluslararası bilimsel toplantılar ile sosyal aktiviteleri içerir.