How to cite this paper
Lelyukh, M., Zhukrovska, M., Komarenska, Z., Flud, V & Harkov, S. (2023). Synthetic approaches, modification ability and biological activity of 1,3,4-thiadiazole based [5+5] annelated heterosystems: Mini-review.Current Chemistry Letters, 12(4), 769-780.
Refrences
1. Barbuceanu S.-F., Saramet G., Almajan G.L., Draghici C., Barbuceanu F., and Bancescu G. (2012) New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation. Eur. J. Med. Chem., 49 417-423.
2. Jain A.K., Sharma S., Vaidya A., Ravichandran V., Agrawal R.K. (2013) 1,3,4-Thiadiazole and its derivatives: A review on recent progress in biological activities. Chem. Biol. Drug Des., 81 557-576.
3. Harish K.P., Mohana K.N., and Mallesha L. (2013) Synthesis of indazole substituted-1,3,4-thiadiazoles and their anticonvulsant activity. Drug Invent. Today, 5 92-99.
4. Kumudha D., Reddy R.R., and Kalavathi T. (2014) Synthesis and evaluation of some 1,3,4-thiadiazoles having substituted 1,2,4-triazole moiety for anticonvulsant and CNS depressant activity. World J. Pharm. Pharm. Sci., 3(9) 728-740.
5. Lelyukh M., Matiichuk Yu., Flud V., Chaban I., and Ogurtsov V. (2022) Synthesis and antioxidant properties of novel 2-(2,4-dioxothiazolidin-5-ylidene)-acetamides containing 1,3,4-thia/oxadiazole moieties. Biointerface Res. Appl. Chem., 12(5) 6710-6722.
6. Mavrova A.Ts., Wesselinova D., Tsenov J.A., and Lubenov L.A. (2014) Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety. Eur. J. Med. Chem., 86(30) 676-683.
7. Wu W.-N., Tai A.-Q., Chen Q., and Ouyang G.-P. (2016) Synthesis and antiviral bioactivity of novel 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-thiadiazole derivatives. J. Het. Chem., 53(2) 626-632.
8. Zhang Y.-B., Wang X.-L., Liu W., Yang Y.-S., Tang J.-F., and Zhu H.-L. (2012) Design, synthesis and biological evaluation of heterocyclic azoles derivatives containing pyrazine moiety as potential telomerase inhibitors. Bioorg. Med. Chem., 20 6356-6365.
9. Tu G.G., Li S.H., Huang H.M., Li G., Xiong F., Mai X., Zhu H.W., Kuang B.H., and Xu W.F. (2008) Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold. Bioorg. Med. Chem., 16(14) 6663-6668.
10. Lelyukh M., Halevych H., Zhukrovska M., Semiion-Luchyshyn O., Kalytovska M. (2023) Synthesis of 5-aryl/heterylidene substituted 2-imino-4-thiazolidinones possessing 1,3,4-thiadiazole moiety and their antitrypanosomal activity. Curr. Chem. Lett., 12(2) 413-420.
11. Haider S., Alam M.S., Hamid H. (2015) 1,3,4-Thiadiazoles: A potent multi targeted pharmacological scaffold. Eur. J. Med. Chem., 92 156-177.
12. Hamama W.S., Ibrahim M.E., Raoof H.A., Zoorob H.H. (2017) Chemistry of bicyclic [1,3,4]thiadiazole 5-5 systems containing ring-junction nitrogen. Res. Chem. Intermed., 43 6259-6291.
13. Lelyukh M., Adamchuk S., Harkov S., Chaban I., Demchuk 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.
14. Ibrahim D.A. (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 2776-2781.
15. Taher A.T., Georgey H.H., El-Subbagh H.I. (2012) Novel 1,3,4-heterodiazole analogues: Synthesis and in-vitro antitumor activity. Eur. J. Med. Chem., 47 445-451.
16. Sahu J.K., Ganguly S., Kaushik A. (2014) Synthesis of some novel heterocyclic 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazole derivatives as possible antimicrobial agents. J. App. Pharm. Sci., 4(02) 081-086.
17. El-Gohary N.S., Shaaban M.I. (2013) Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles. Eur. J. Med. Chem., 63 185-195.
18. El-Gohary N.S., Shaaban M.I. (2014) Antimicrobial and antiquorum-sensing studies. Part 2: Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of fused [1,3,4]thiadiazole and [1,3]benzothiazole derivatives. Med. Chem. Res., 23 287-299.
19. Chandrakantha B., Isloor A.M., Shetty P., Fun H.K., Hegde G. (2014) Synthesis and biological evaluation of novel substituted 1,3,4-thiadiazole and 2,6-diaryl substituted imidazo[2,1-b][1,3,4]-thiadiazole derivatives. Eur. J. Med. Chem., 71 316-323.
20. Zhang Y., Li Z.-M., Song H.-B., Wang B.-L. (2018) Synthesis, structure and biological activities of novel 2-(trifluoromethyl)-6-arylimidazo[2,1-b][1,3,4]-thiadiazole (bis-)Mannich base derivatives containing substituted piperazine moiety. Chin. J. Chem., 36(7) 635-638.
21. Cansiz A., Cetin A., Orek C., Karatepe M., Sarac K., Kus A., Koparir P. (2012) 6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: Synthesis, experimental, theoretical characterization and biological activities. Spectrochim. Acta A Mol. Biomol. Spectrosc., 97 606-615.
22. Seelolla G., Ponneri V. (2016) Synthesis, antimicrobial, and antioxidant activities of some fused heterocyclic [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives. J. Het. Chem., 53(3) 929-936.
23. Pandey V.K., Tusi Z., Tandon M. (2003) Synthesis of thiadiazolo-s-triazines for their antiviral activity based on QSAR studies. Indian J. Chem., 42B 2583-2588.
24. El Shehry M.F., Abu-Hachem A.A., El-Telbani E.M. (2010) Synthesis of 3-((2,4-dichlorophenoxy)-methyl)-1,2,4-triazolo(thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. Eur. J. Med. Chem., 45 1906-1911.
25. Domingo L.R. (2016) Molecular Electron Density Theory: A modern view of reactivity in organic chemistry. Molecules, 21(10) 1319.
26. Sadowski S., Utnicka J., Wójtowicz A., Kula K. (2023) The global and local reactivity of C,N-diarylnitryle imines in [3+2] cycloaddition processes with trans-β-nitrostyrene according to Molecular Electron Density Theory: A computational study. Curr. Chem. Lett., 12(2) 421-430.
27. Kula K., Łapczuk A., Sadowski M., Kras J., Zawadzińska K., Demchuk O.M., Gaurav G.K., Wróblewska A., Jasiński R. (2022) On the question of the formation of nitro-functionalized 2,4-pyrazole analogs on the basis of nitrylimine molecular systems and 3,3,3-trichloro-1-nitroprop-1-ene. Molecules, 27(23) 840.
28. Zawadzińska K., Ríos-Gutiérrez M., Kula K., Woliński P., Mirosław B., Krawczyk T., Jasiński R. (2021) The participation of 3,3,3-trichloro-1-nitroprop-1-ene in the [3+2] cycloaddition with selected nitrile N-oxides in the light of the experimental and MEDT quantum chemical study. Molecules, 26(22) 6774.
29. Jasiński R. (2023) On the question of selective protocol for the preparation of juglone via (4+2) cycloaddition involving 3-hydroxypyridazine: DFT mechanistic study. Chem. Heterocycl. Compd., 59(3) 138-144.
30. Subtelna I., Kryshchyshyn-Dylevych A., Jia R., Lelyukh M., Ringler A., Kubicek S., Zagrijtschuk O., Kralovics R., Lesyk R. (2021) 5-Arylidene-2-(4-hydroxyphenyl)aminothiazol-4(5H)-ones with selective inhibitory activity against some leukemia cell line. Arch. Pharm., 354(4) 2000342.
31. El Tabl A., Zawam S., Sarhan K. (2021) Innovating new methods for wastewater treatment in El-Dakhla Oasis in Upper Egypt from chemical and biological pollutants using modified down Flow Hanging Sponge (DHS) reactor in presence of new environmental friendly chelator. Egypt. J. Chem., 64(9) 4985-4994.
32. Elhady O.M., Mansour E.S., Elwassimy M.M., Zawam S.A., Drar A.M., Abdel-Raheem S.A.A. (2022) Selective synthesis, characterization, and toxicological activity screening of some furan compounds as pesticidal agents. Curr. Chem. Lett., 11(3) 285-290.
33. Lelyukh M., Pylypchuk I., Kalytovska M., Harkov S., Kostyshyn L., Drapak I. (2022) Synthesis and anti-cancer activity evaluation of novel 1,3,4-oxadiazole substituted 5-arylidene/isatinylidene-2- iminothiazolidin-4-ones. Biointerface Res. Appl. Chem., 12(1) 1161-1173.
34. Shamsan A.Q.S., Fouad M.R., Yacoob W.A.R.M., Abdul-Malik M.A., Abdel-Raheem S.A.A. (2023) Performance of a variety of treatment processes to purify wastewater in the food industry. Curr. Chem. Lett., 12(2) 431-438.
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2. Jain A.K., Sharma S., Vaidya A., Ravichandran V., Agrawal R.K. (2013) 1,3,4-Thiadiazole and its derivatives: A review on recent progress in biological activities. Chem. Biol. Drug Des., 81 557-576.
3. Harish K.P., Mohana K.N., and Mallesha L. (2013) Synthesis of indazole substituted-1,3,4-thiadiazoles and their anticonvulsant activity. Drug Invent. Today, 5 92-99.
4. Kumudha D., Reddy R.R., and Kalavathi T. (2014) Synthesis and evaluation of some 1,3,4-thiadiazoles having substituted 1,2,4-triazole moiety for anticonvulsant and CNS depressant activity. World J. Pharm. Pharm. Sci., 3(9) 728-740.
5. Lelyukh M., Matiichuk Yu., Flud V., Chaban I., and Ogurtsov V. (2022) Synthesis and antioxidant properties of novel 2-(2,4-dioxothiazolidin-5-ylidene)-acetamides containing 1,3,4-thia/oxadiazole moieties. Biointerface Res. Appl. Chem., 12(5) 6710-6722.
6. Mavrova A.Ts., Wesselinova D., Tsenov J.A., and Lubenov L.A. (2014) Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety. Eur. J. Med. Chem., 86(30) 676-683.
7. Wu W.-N., Tai A.-Q., Chen Q., and Ouyang G.-P. (2016) Synthesis and antiviral bioactivity of novel 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-thiadiazole derivatives. J. Het. Chem., 53(2) 626-632.
8. Zhang Y.-B., Wang X.-L., Liu W., Yang Y.-S., Tang J.-F., and Zhu H.-L. (2012) Design, synthesis and biological evaluation of heterocyclic azoles derivatives containing pyrazine moiety as potential telomerase inhibitors. Bioorg. Med. Chem., 20 6356-6365.
9. Tu G.G., Li S.H., Huang H.M., Li G., Xiong F., Mai X., Zhu H.W., Kuang B.H., and Xu W.F. (2008) Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold. Bioorg. Med. Chem., 16(14) 6663-6668.
10. Lelyukh M., Halevych H., Zhukrovska M., Semiion-Luchyshyn O., Kalytovska M. (2023) Synthesis of 5-aryl/heterylidene substituted 2-imino-4-thiazolidinones possessing 1,3,4-thiadiazole moiety and their antitrypanosomal activity. Curr. Chem. Lett., 12(2) 413-420.
11. Haider S., Alam M.S., Hamid H. (2015) 1,3,4-Thiadiazoles: A potent multi targeted pharmacological scaffold. Eur. J. Med. Chem., 92 156-177.
12. Hamama W.S., Ibrahim M.E., Raoof H.A., Zoorob H.H. (2017) Chemistry of bicyclic [1,3,4]thiadiazole 5-5 systems containing ring-junction nitrogen. Res. Chem. Intermed., 43 6259-6291.
13. Lelyukh M., Adamchuk S., Harkov S., Chaban I., Demchuk 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.
14. Ibrahim D.A. (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 2776-2781.
15. Taher A.T., Georgey H.H., El-Subbagh H.I. (2012) Novel 1,3,4-heterodiazole analogues: Synthesis and in-vitro antitumor activity. Eur. J. Med. Chem., 47 445-451.
16. Sahu J.K., Ganguly S., Kaushik A. (2014) Synthesis of some novel heterocyclic 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazole derivatives as possible antimicrobial agents. J. App. Pharm. Sci., 4(02) 081-086.
17. El-Gohary N.S., Shaaban M.I. (2013) Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles. Eur. J. Med. Chem., 63 185-195.
18. El-Gohary N.S., Shaaban M.I. (2014) Antimicrobial and antiquorum-sensing studies. Part 2: Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of fused [1,3,4]thiadiazole and [1,3]benzothiazole derivatives. Med. Chem. Res., 23 287-299.
19. Chandrakantha B., Isloor A.M., Shetty P., Fun H.K., Hegde G. (2014) Synthesis and biological evaluation of novel substituted 1,3,4-thiadiazole and 2,6-diaryl substituted imidazo[2,1-b][1,3,4]-thiadiazole derivatives. Eur. J. Med. Chem., 71 316-323.
20. Zhang Y., Li Z.-M., Song H.-B., Wang B.-L. (2018) Synthesis, structure and biological activities of novel 2-(trifluoromethyl)-6-arylimidazo[2,1-b][1,3,4]-thiadiazole (bis-)Mannich base derivatives containing substituted piperazine moiety. Chin. J. Chem., 36(7) 635-638.
21. Cansiz A., Cetin A., Orek C., Karatepe M., Sarac K., Kus A., Koparir P. (2012) 6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: Synthesis, experimental, theoretical characterization and biological activities. Spectrochim. Acta A Mol. Biomol. Spectrosc., 97 606-615.
22. Seelolla G., Ponneri V. (2016) Synthesis, antimicrobial, and antioxidant activities of some fused heterocyclic [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives. J. Het. Chem., 53(3) 929-936.
23. Pandey V.K., Tusi Z., Tandon M. (2003) Synthesis of thiadiazolo-s-triazines for their antiviral activity based on QSAR studies. Indian J. Chem., 42B 2583-2588.
24. El Shehry M.F., Abu-Hachem A.A., El-Telbani E.M. (2010) Synthesis of 3-((2,4-dichlorophenoxy)-methyl)-1,2,4-triazolo(thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. Eur. J. Med. Chem., 45 1906-1911.
25. Domingo L.R. (2016) Molecular Electron Density Theory: A modern view of reactivity in organic chemistry. Molecules, 21(10) 1319.
26. Sadowski S., Utnicka J., Wójtowicz A., Kula K. (2023) The global and local reactivity of C,N-diarylnitryle imines in [3+2] cycloaddition processes with trans-β-nitrostyrene according to Molecular Electron Density Theory: A computational study. Curr. Chem. Lett., 12(2) 421-430.
27. Kula K., Łapczuk A., Sadowski M., Kras J., Zawadzińska K., Demchuk O.M., Gaurav G.K., Wróblewska A., Jasiński R. (2022) On the question of the formation of nitro-functionalized 2,4-pyrazole analogs on the basis of nitrylimine molecular systems and 3,3,3-trichloro-1-nitroprop-1-ene. Molecules, 27(23) 840.
28. Zawadzińska K., Ríos-Gutiérrez M., Kula K., Woliński P., Mirosław B., Krawczyk T., Jasiński R. (2021) The participation of 3,3,3-trichloro-1-nitroprop-1-ene in the [3+2] cycloaddition with selected nitrile N-oxides in the light of the experimental and MEDT quantum chemical study. Molecules, 26(22) 6774.
29. Jasiński R. (2023) On the question of selective protocol for the preparation of juglone via (4+2) cycloaddition involving 3-hydroxypyridazine: DFT mechanistic study. Chem. Heterocycl. Compd., 59(3) 138-144.
30. Subtelna I., Kryshchyshyn-Dylevych A., Jia R., Lelyukh M., Ringler A., Kubicek S., Zagrijtschuk O., Kralovics R., Lesyk R. (2021) 5-Arylidene-2-(4-hydroxyphenyl)aminothiazol-4(5H)-ones with selective inhibitory activity against some leukemia cell line. Arch. Pharm., 354(4) 2000342.
31. El Tabl A., Zawam S., Sarhan K. (2021) Innovating new methods for wastewater treatment in El-Dakhla Oasis in Upper Egypt from chemical and biological pollutants using modified down Flow Hanging Sponge (DHS) reactor in presence of new environmental friendly chelator. Egypt. J. Chem., 64(9) 4985-4994.
32. Elhady O.M., Mansour E.S., Elwassimy M.M., Zawam S.A., Drar A.M., Abdel-Raheem S.A.A. (2022) Selective synthesis, characterization, and toxicological activity screening of some furan compounds as pesticidal agents. Curr. Chem. Lett., 11(3) 285-290.
33. Lelyukh M., Pylypchuk I., Kalytovska M., Harkov S., Kostyshyn L., Drapak I. (2022) Synthesis and anti-cancer activity evaluation of novel 1,3,4-oxadiazole substituted 5-arylidene/isatinylidene-2- iminothiazolidin-4-ones. Biointerface Res. Appl. Chem., 12(1) 1161-1173.
34. Shamsan A.Q.S., Fouad M.R., Yacoob W.A.R.M., Abdul-Malik M.A., Abdel-Raheem S.A.A. (2023) Performance of a variety of treatment processes to purify wastewater in the food industry. Curr. Chem. Lett., 12(2) 431-438.
35. Kochar M.M., Salahi-Asbani M., Williams B.B. (1973) Bicyclic thiadiazoles I: 2-(2-Thienyl)-5-phenylthiazolo[2,3-b]-1,3,4-thiadiazole. J. Pharm. Sci., 62(2) 336-337.
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