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How to cite this paper
APA: Myrko, I., Chaban, T., Horak, Y., Ogurtsov, V., Drapak, I., Chaban, I & Matiychuk, V. (2023). Anticancer properties of some triazolo[3,4-b][1,3,4]thiadiazoles. Current Chemistry Letters, 12(4), 813-820.
Chicago/Turabian: Myrko, I., Chaban, T., Horak, Y., Ogurtsov, V., Drapak, I., Chaban, I & Matiychuk, V. 2023. "Anticancer properties of some triazolo[3,4-b][1,3,4]thiadiazoles." Current Chemistry Letters 12, no. 4 (2023): 813-820.
AMA: Myrko, I., Chaban, T., Horak, Y., Ogurtsov, V., Drapak, I., Chaban, I & Matiychuk, V. Anticancer properties of some triazolo[3,4-b][1,3,4]thiadiazoles. Current Chemistry Letters. 2023;12(4):813-820.
References
1. Sung H., Ferlay J., Siegel R. L., Laversanne M., Soerjomataram I., Jemal A., Bray F. (2021) Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: Cancer J. Clin. 71 (3) 209-249.
2. Schirrmacher V. (2019) From chemotherapy to biological therapy: A review of novel concepts to reduce the side effects of systemic cancer treatment. Int. J. Oncol. 54 (2) 407-419.
3. Kerru N., Gummidi L., Maddila S., Gangu K., Jonnalagadda S. (2020) A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules, 25 (8) 1909.
4. Kumar D., Kumar Jain S. (2016) A comprehensive review of N-heterocycles as cytotoxic agents. Curr. Med. Chem. 23 (38) 4338-4394.
5. Asif M. (2017) A mini review: biological significances of nitrogen hetero atom containing heterocyclic compounds. Int. J. Bioorg. Chem 2 (3) 146-152.
6. Khattab T. A., Rehan M. (2018) A review on synthesis of nitrogen-containing heterocyclic dyes for textile fibers-Part 2: Fused heterocycles. Egypt. J. Chem. 61 (6) 989-1018.
7. Sonawane R. K., Mohite S. K. (2021) Heterocyclic bridgehead nitrogen atom system: review on [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole and its pharmacological screening. Asian Journal of Research in Chemistry 14 (3) 217‒220.
8. Ibrahim D. (2009) Synthesis and biological evaluation of 3,6-disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as a novel class of potential anti-tumor agents. Eur. J. Med. Chem. 44 (7) 2776‒2781.
9. Kamel M., Megally Abdo, N. (2014) Synthesis of novel 1,2,4-triazoles, triazolothiadiazines and triazolothiadiazoles as potential anticancer agents. Eur. J. Med. Chem. 86 75‒80.
10. Rostom S., Badr M., Razik H., Ashour H. (2017) Structure-based development of novel triazoles and related thiazolotriazoles as anticancer agents and Cdc25A/B phosphatase inhibitors. Synthesis, in-vitro biological evaluation, molecular docking and in-silico ADME-T studies. Eur. J. Med. Chem. 139 263‒279.
11. Kumar G., Prasad Y., Mallikarjuna B., Chandrashekar S. (2010) Synthesis and pharmacological evaluation of clubbed isopropylthiazole derived triazolothiadiazoles, triazolothiadiazines and Mannich bases as potential antimicrobial and antitubercular agents. Eur. J. Med. Chem. 45 (11) 5120‒5129.
12. Cui P., Li X., Zhu M., Wang B., Liu J., Chen H. (2017) Design, synthesis and antimicrobial activities of thiouracil derivatives containing triazolo- thiadiazole as SecA inhibitors. Eur. J. Med. Chem. 127 159‒165.
13. Jubie S., Ramesh P., Dhanabal P., Kalirajan R., Muruganantham N., Antony A. (2012) Synthesis, antidepressant and antimicrobial activities of some novel stearic acid analogues. Eur. J. Med. Chem. 54 931‒935.
14. Deng X., Dong Z., Song M., Shu B., Wang S., Quan, Z. (2012) Synthesis and anticonvulsant activities of some triazolothiadiazole derivatives. Arch. Pharm. 345 (7) 565‒573.
15. Bonafoux D., Nanthakumar S., Bandarage U., Memmott C., Lowe D., Aronov A., Rao Bhisetti G., Bonanno K., Coll J., Leeman J., Lepre C., Lu F., Perola E., Rijnbrand R., Taylor W., Wilson D., Zhou Y., Zwahlen J., Haar E. (2016) Fragment-Based Discovery of Dual JC Virus and BK Virus Helicase Inhibitors. J. Med. Chem. 59 (15) 7138‒7151.
16. Khan I., Ibrar A., Zaib S., Ahmad S., Furtmann N., Hameed S., Simpson J., Bajorath J., Iqbal J. (2014). Active compounds from a diverse library of triazolothiadiazole and triazolothiadiazine scaffolds: Synthesis, crystal structure determination, cytotoxicity, cholinesterase inhibitory activity, and binding mode analysis. Bioorg. Med. Chem. 22 (21) 6163‒6173.
17. Ram S., Celik G., Khloya P., Vullo D., Supuran C., Sharma P. (2014) Benzenesulfonamide bearing 1,2,4-triazole scaffolds as potent inhibitors of tumor associated carbonic anhydrase isoforms hCA IX and hCA XII. Bioorg. Med. Chem. 22 (6) 1873‒1882.
18. Yuan H., Liu Q., Zhang L,. Hu S., Chen T., Li H., Chen Y., Xu Y., Lu T. (2018) Discovery, optimization and biological evaluation for novel c-Met kinase inhibitors. Eur. J. Med. Chem., 143 491‒502.
19. Chaban T., Matiychuk V., Mahlovanyy A., Chaban I., Ogurtsov V. and Leluykh M. (2020) Synthesis and biological evaluation of 1-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-3-(2-oxo-2-(10H-phenothiazin-10-yl)ethyl)urea derivatives. Biointerface Res. Appl. Chem. 10 (4) 5944–5950.
20. Obushak M., Matiychuk V., Turytsya V. (2009) A new approach to the synthesis of 3,4-dihydroisocoumarin derivatives. Tetrahedron Lett. 50 (45) 6112-6115.
21. Chaban T., Matiychuk V., Ogurtsov V., Chaban I. and Nektegayev I. (2020) Development of effective anti-inflammatory drug candidates among novel thiazolopyridines. Ukr. Biochem. J. 92 (2) 132–139.
22. Rydchuk P., Tymoshuk O., Oleksiv L., Chaban T. and Matiychuk V. (2019) Voltammetric Determination of Pt(IV) using 5-Hydroxyimino-4- imino-1,3-thiazolidine-2-one. Methods Objects Chem. Anal. 14 (3) 130–139.
23. Chaban T. Matiichuk Y., Horishny V., Chaban I. and Matiychuk V. (2020) Synthesis and anticancer activity of 2-aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-dione and 2-aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones. Russ. J. Org. Chem. 56 (5) 813–818.
24. Tsyalkovsky V., Kutsyk R., Matiychuk V., Obushak N., Klyufinskaya T. (2005) Synthesis and antimicrobial activity of 5-(R1-benzyl)-2-(R 2-benzylidenehydrazono)-3-(2-furylmethyl)thiazolidin-4-ones. Pharm. Chem. J. 39 (5) 245-247.
25. Сhulovska Z., Drapak I., Chaban T., Ogurtsov V., Matiychuk V. (2021) Synthesis, anticancer and antioxidant properties of some 4-thioxo-thiazolidin-2-ones. Eur. Chem. Bull. 10 (4) 147-154.
26. Lelyukh M., Martynets M., Kalytovska M., Drapak I., Harkov S., Chaban T., Chaban I., Matiychuk V. (2020) Approaches for synthesis and chemical modification of non-condensed heterocyclic systems based on 1, 3, 4-oxadiazole ring and their biological activity: A review. J. Appl. Pharm. Sci., 10 (10) 151-165.
27. Drapak I., Foliush V., Chaban T. and Matiychuk V. (2020) Synthesis antimicrobial and antitumor activities of 2-[5-(2-R-benzyl)thiazol-2-ylimino]thiazolidin-4-ones. Biointerface Res. Appl. Chem. 10 (3) 5507–5511.
28. Сhulovska Z., Chaban T., Drapak I., Chaban I. and Nektegaev I. (2021) Synthesis of some С5 substituted 4-phenylimino-thiazolidin-2-ones as possible anti-inflammatory agents. Biointerface Res. Appl. Chem. 11 (1) 8009–8017.
29. Lelyukh M., Adamchuk S., Harkov S., Demchuk I., Chaban I., Shelepeten L., Chaban T. (2018) Synthetic approaches, chemical modification and biological activity of non-condensed 1,3,4-thiadiazole derivatives: A review. Pharmacia 65 (4) 72–88.
30. Developmental Therapeutics Program. Available online: http://dtp.nci.nih.gov.
31. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A. (1991) Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. J. Nat. Cancer Inst. 83 (11) 757-766.
32. Boyd M. R., Paull K. D. (1995) Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Dev. Res. 34 (1) 91-109.
33. Shoemaker R. H. (2006) The NCI60 human tumour cell line anticancer drug screen. Nat. Rev. Cancer 6 (10) 813-823.
1. Sung H., Ferlay J., Siegel R. L., Laversanne M., Soerjomataram I., Jemal A., Bray F. (2021) Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: Cancer J. Clin. 71 (3) 209-249.
2. Schirrmacher V. (2019) From chemotherapy to biological therapy: A review of novel concepts to reduce the side effects of systemic cancer treatment. Int. J. Oncol. 54 (2) 407-419.
3. Kerru N., Gummidi L., Maddila S., Gangu K., Jonnalagadda S. (2020) A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules, 25 (8) 1909.
4. Kumar D., Kumar Jain S. (2016) A comprehensive review of N-heterocycles as cytotoxic agents. Curr. Med. Chem. 23 (38) 4338-4394.
5. Asif M. (2017) A mini review: biological significances of nitrogen hetero atom containing heterocyclic compounds. Int. J. Bioorg. Chem 2 (3) 146-152.
6. Khattab T. A., Rehan M. (2018) A review on synthesis of nitrogen-containing heterocyclic dyes for textile fibers-Part 2: Fused heterocycles. Egypt. J. Chem. 61 (6) 989-1018.
7. Sonawane R. K., Mohite S. K. (2021) Heterocyclic bridgehead nitrogen atom system: review on [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole and its pharmacological screening. Asian Journal of Research in Chemistry 14 (3) 217‒220.
8. Ibrahim D. (2009) Synthesis and biological evaluation of 3,6-disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as a novel class of potential anti-tumor agents. Eur. J. Med. Chem. 44 (7) 2776‒2781.
9. Kamel M., Megally Abdo, N. (2014) Synthesis of novel 1,2,4-triazoles, triazolothiadiazines and triazolothiadiazoles as potential anticancer agents. Eur. J. Med. Chem. 86 75‒80.
10. Rostom S., Badr M., Razik H., Ashour H. (2017) Structure-based development of novel triazoles and related thiazolotriazoles as anticancer agents and Cdc25A/B phosphatase inhibitors. Synthesis, in-vitro biological evaluation, molecular docking and in-silico ADME-T studies. Eur. J. Med. Chem. 139 263‒279.
11. Kumar G., Prasad Y., Mallikarjuna B., Chandrashekar S. (2010) Synthesis and pharmacological evaluation of clubbed isopropylthiazole derived triazolothiadiazoles, triazolothiadiazines and Mannich bases as potential antimicrobial and antitubercular agents. Eur. J. Med. Chem. 45 (11) 5120‒5129.
12. Cui P., Li X., Zhu M., Wang B., Liu J., Chen H. (2017) Design, synthesis and antimicrobial activities of thiouracil derivatives containing triazolo- thiadiazole as SecA inhibitors. Eur. J. Med. Chem. 127 159‒165.
13. Jubie S., Ramesh P., Dhanabal P., Kalirajan R., Muruganantham N., Antony A. (2012) Synthesis, antidepressant and antimicrobial activities of some novel stearic acid analogues. Eur. J. Med. Chem. 54 931‒935.
14. Deng X., Dong Z., Song M., Shu B., Wang S., Quan, Z. (2012) Synthesis and anticonvulsant activities of some triazolothiadiazole derivatives. Arch. Pharm. 345 (7) 565‒573.
15. Bonafoux D., Nanthakumar S., Bandarage U., Memmott C., Lowe D., Aronov A., Rao Bhisetti G., Bonanno K., Coll J., Leeman J., Lepre C., Lu F., Perola E., Rijnbrand R., Taylor W., Wilson D., Zhou Y., Zwahlen J., Haar E. (2016) Fragment-Based Discovery of Dual JC Virus and BK Virus Helicase Inhibitors. J. Med. Chem. 59 (15) 7138‒7151.
16. Khan I., Ibrar A., Zaib S., Ahmad S., Furtmann N., Hameed S., Simpson J., Bajorath J., Iqbal J. (2014). Active compounds from a diverse library of triazolothiadiazole and triazolothiadiazine scaffolds: Synthesis, crystal structure determination, cytotoxicity, cholinesterase inhibitory activity, and binding mode analysis. Bioorg. Med. Chem. 22 (21) 6163‒6173.
17. Ram S., Celik G., Khloya P., Vullo D., Supuran C., Sharma P. (2014) Benzenesulfonamide bearing 1,2,4-triazole scaffolds as potent inhibitors of tumor associated carbonic anhydrase isoforms hCA IX and hCA XII. Bioorg. Med. Chem. 22 (6) 1873‒1882.
18. Yuan H., Liu Q., Zhang L,. Hu S., Chen T., Li H., Chen Y., Xu Y., Lu T. (2018) Discovery, optimization and biological evaluation for novel c-Met kinase inhibitors. Eur. J. Med. Chem., 143 491‒502.
19. Chaban T., Matiychuk V., Mahlovanyy A., Chaban I., Ogurtsov V. and Leluykh M. (2020) Synthesis and biological evaluation of 1-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-3-(2-oxo-2-(10H-phenothiazin-10-yl)ethyl)urea derivatives. Biointerface Res. Appl. Chem. 10 (4) 5944–5950.
20. Obushak M., Matiychuk V., Turytsya V. (2009) A new approach to the synthesis of 3,4-dihydroisocoumarin derivatives. Tetrahedron Lett. 50 (45) 6112-6115.
21. Chaban T., Matiychuk V., Ogurtsov V., Chaban I. and Nektegayev I. (2020) Development of effective anti-inflammatory drug candidates among novel thiazolopyridines. Ukr. Biochem. J. 92 (2) 132–139.
22. Rydchuk P., Tymoshuk O., Oleksiv L., Chaban T. and Matiychuk V. (2019) Voltammetric Determination of Pt(IV) using 5-Hydroxyimino-4- imino-1,3-thiazolidine-2-one. Methods Objects Chem. Anal. 14 (3) 130–139.
23. Chaban T. Matiichuk Y., Horishny V., Chaban I. and Matiychuk V. (2020) Synthesis and anticancer activity of 2-aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-dione and 2-aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones. Russ. J. Org. Chem. 56 (5) 813–818.
24. Tsyalkovsky V., Kutsyk R., Matiychuk V., Obushak N., Klyufinskaya T. (2005) Synthesis and antimicrobial activity of 5-(R1-benzyl)-2-(R 2-benzylidenehydrazono)-3-(2-furylmethyl)thiazolidin-4-ones. Pharm. Chem. J. 39 (5) 245-247.
25. Сhulovska Z., Drapak I., Chaban T., Ogurtsov V., Matiychuk V. (2021) Synthesis, anticancer and antioxidant properties of some 4-thioxo-thiazolidin-2-ones. Eur. Chem. Bull. 10 (4) 147-154.
26. Lelyukh M., Martynets M., Kalytovska M., Drapak I., Harkov S., Chaban T., Chaban I., Matiychuk V. (2020) Approaches for synthesis and chemical modification of non-condensed heterocyclic systems based on 1, 3, 4-oxadiazole ring and their biological activity: A review. J. Appl. Pharm. Sci., 10 (10) 151-165.
27. Drapak I., Foliush V., Chaban T. and Matiychuk V. (2020) Synthesis antimicrobial and antitumor activities of 2-[5-(2-R-benzyl)thiazol-2-ylimino]thiazolidin-4-ones. Biointerface Res. Appl. Chem. 10 (3) 5507–5511.
28. Сhulovska Z., Chaban T., Drapak I., Chaban I. and Nektegaev I. (2021) Synthesis of some С5 substituted 4-phenylimino-thiazolidin-2-ones as possible anti-inflammatory agents. Biointerface Res. Appl. Chem. 11 (1) 8009–8017.
29. Lelyukh M., Adamchuk S., Harkov S., Demchuk I., Chaban I., Shelepeten L., Chaban T. (2018) Synthetic approaches, chemical modification and biological activity of non-condensed 1,3,4-thiadiazole derivatives: A review. Pharmacia 65 (4) 72–88.
30. Developmental Therapeutics Program. Available online: http://dtp.nci.nih.gov.
31. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A. (1991) Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. J. Nat. Cancer Inst. 83 (11) 757-766.
32. Boyd M. R., Paull K. D. (1995) Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Dev. Res. 34 (1) 91-109.
33. Shoemaker R. H. (2006) The NCI60 human tumour cell line anticancer drug screen. Nat. Rev. Cancer 6 (10) 813-823.