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Applied Sciences OPEN ACCESS

Synthesis Of 2,5-Dimersapto-1,3,4-Thiadiazol Products

Jololiddinov Fazliddin Yuldashali Ugli
Trainee-Researcher Of Academic Institute Of Bioorganic Chemistry Named After O.S Sodikov Laboratory Of Low Molecular Weight Biologically Active Compounds, Uzbekistan
Xaitboev Xamid
Senior Researcher, Candidate Of Chemical Sciences Of Academic Institute Of Bioorganic Chemistry Named After Os Sodikov Laboratory Of Low Molecular Biologically Active Compounds, Uzbekistan
Boboev Baxrom Nurillaevich
Doctor Of Chemical Sciences, Professor, Head Of The Department Of Chemistry Of Natural Compounds, Faculty Of Chemistry, National University Of Uzbekistan
DOI Crossref DOI 10.37547/tajas/Volume02Issue09-23
tajas 2020
VOL. 2 / NO. 09 SEPTEMBER
FULL TEXT PP. 143-153
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VOLUME 2
ISSUE 09
YEAR 2020
PAGES 143-153
RESEARCH OVERVIEW

Abstract

Potentially bioactive 2,5-bis derivatives of 1,3,4-thiadiazole with alkaloid moieties were synthesized byreaction of 1,3,4-thiadiazol-2,5-dithiol with N-acryloyl-substituted derivatives of the alkaloids anabasine,cytisine, and D-pseudoephedrine.1,3,4-Thiadiazole-2,5-disulfonic acid was synthesized by oxidation of 2,5-dimercapto-1,3,4-thiadiazole,and onium salts of this acid were prepared by its reactions with selected alkaloids and secondaryamines.

 

RESEARCH TOPICS

Keywords

Synthesis 1,3,4-thiadiazol-2,5-dithiol alkaloids

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References

  1. Yang Hu,Cui-Yun Li,Xiao-Ming Wang,Yong-Hua Yang, and Hai-Liang Zhu.,1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal,Agricultural, and Materials Chemistry.,Chem. Rev.2014, 114, 10, 5572–5610.
  2. KratikaShrivastava, Suresh Purohit and SaritaSinghal. Studies On Nitrogen And Sulphur Containing Heterocyclic Compound: 1,3,4 – thiadiazole. Asian Journal of Biomedical and Pharmaceutical Sciences 3(21) 2013, 6-23.
  3. Jigar K. Mistry, Richard Dawes, AmitavaChoudhury, and Michael R. Van De Mark., 5-Mercapto-1,3,4-thiadiazole-2(3H)-thione: Synthesis and Structure of Alkylated Derivatives., 2014 May Journal of Heterocyclic Chemistry 51(3):747 – 754.
  4. Shaker Awad Abdul Hussein and Ammar Abdul Razzak M. Kubba.,Synthesis, characterization and antimicrobial activity of new 2,5-disubstituted-1,3,4-thiadiazole derivatives., Der PharmaChemica, 2015, 7 (9):250-260.
  5. Liu, F., Luo, X.-Q., Song, B.-A., Bhadury, P. S., Yang, S., Jin, L.-H.,Hu, D.-Y. Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety. Bioorganic & Medicinal Chemistry, (2008).16(7), 3632–3640.
  6. Chen, C.-J., Song, B.-A., Yang, S., Xu, G.-F., Bhadury, P. S., Jin, L.-H., Chen, Z.Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives. Bioorganic & Medicinal Chemistry, (2007)15(12), 3981–3989
  7. Zoumpoulakis, P., Camoutsis, C., Pairas, G., Soković, M., Glamočlija, J., Potamitis, C., &Pitsas, A.Synthesis of novel sulfonamide-1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, as potential antibacterial and antifungal agents. Biological evaluation and conformational analysis studies.Bioorganic & Medicinal Chemistry, (2012)20(4)
  8. Alwan, W. S., Karpoormath, R., Palkar, M. B., Patel, H. M., Rane, R. A., Shaikh, M. S., … Mlisana, K. P. Novel imidazo[2,1-b]-1,3,4-thiadiazoles as promising antifungal agents against clinical isolate of Cryptococcus neoformans. European Journal of Medicinal Chemistry, (2015).95, 514–525.
  9. Wu, Q., Cai, H., Yuan, T., Li, S., Gan, X., & Song, B. Novel vanillin derivatives containing a 1,3,4-thiadiazole moiety as potential antibacterial agents. Bioorganic & Medicinal Chemistry Letters, (2020).127113.
  10. Chen, J., Yi, C., Wang, S., Wu, S., Li, S., Hu, D., & Song, B. Novel amide derivatives containing 1,3,4-thiadiazole moiety: Design, synthesis, nematocidal and antibacterial activities. Bioorganic & Medicinal Chemistry Letters. 29 (2019) 1203–1210.
  11. Li, P., Shi, L., Yang, X., Yang, L., Chen, X.-W., Wu, F., … Song, B.-A. Design, synthesis, and antibacterial activity against rice bacterial leaf blight and leaf streak of 2,5-substituted-1,3,4-oxadiazole/thiadiazolesulfone derivative. Bioorganic & Medicinal Chemistry Letters, (2014). 24(7), 1677–1680.
  12. Li, P., Shi, L., Gao, M.-N., Yang, X., Xue, W., Jin, L.-H., Song, B.-A. Antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives. Bioorganic & Medicinal Chemistry Letters, (2015).25(3), 481–484
  13. Ragab, F. A., Heiba, H. I., El-Gazzar, M. G., Abou-Seri, S. M., El-Sabbagh, W. A., & El-Hazek, R. M. Anti-inflammatory, analgesic and COX-2 inhibitory activity of novel thiadiazoles in irradiated rats. Journal of Photochemistry and Photobiology B: Biology, (2017).166, 285–300.
  14. Omar, Y. M., Abdu-Allah, H. H. M., & Abdel-Moty, S. G.. Synthesis, biological evaluation and docking study of 1,3,4-thiadiazole-thiazolidinone hybrids as anti-inflammatory agents with dual inhibition of COX-2 and 15-LOX. Bioorganic Chemistry, (2018), 80, 461–471.
  15. Maddila, S., Gorle, S., Sampath, C., &Lavanya, P. Synthesis and anti-inflammatory activity of some new 1,3,4-thiadiazoles containing pyrazole and pyrrole nucleus. Journal of Saudi Chemical Society, (2016).20, S306–S312.
  16. Hafez, H. N., Hegab, M. I., Ahmed-Farag, I. S., & El-Gazzar, A. B. A.A facile regioselective synthesis of novel spiro-thioxanthene and spiro-xanthene-9′,2-[1,3,4]thiadiazole derivatives as potential analgesic and anti-inflammatory agents. Bioorganic & Medicinal Chemistry Letters, (2008).18(16), 4538–4543
  17. Salgın-Gökşen, U., Gökhan-Kelekçi, N., Göktaş, Ö.,Köysal, Y., Kılıç, E., Işık, Ş.,Özalp, M. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: Synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorganic & Medicinal Chemistry, (2007).15(17), 5738–5751.
  18. Almandil, N. B., Taha, M., Rahim, F., Wadood, A., Imran, S., Alqahtani, M. A.,Gollapalli, M. Synthesis of novel quinoline-based thiadiazole, evaluation of their antileishmanial potential and molecular docking studies. Bioorganic Chemistry, (2019).85, 109–116.
  19. Tahghighi, A., Marznaki, F. R., Kobarfard, F., Dastmalchi, S., Mojarrad, J. S., Razmi, S., …Foroumadi, A. Synthesis and antileishmanial activity of novel 5-(5-nitrofuran-2-y1)-1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituents. European Journal of Medicinal Chemistry, (2011).46(6), 2602–2608.
  20. Wei, M.-X., Feng, L., Li, X.-Q., Zhou, X.-Z., & Shao, Z.-H. Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity. European Journal of Medicinal Chemistry, (2009).44(8), 3340–3344.
  21. Kumar, D., Maruthi Kumar, N., Chang, K.-H., & Shah, K. Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles. European Journal of Medicinal Chemistry, (2010).45(10), 4664–4668.
  22. Kumar, D., Kumar, N. M., Chang, K.-H., Gupta, R., & Shah, K..Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles. Bioorganic & Medicinal Chemistry Letters, (2011) 21(19), 5897–5900.
  23. Jakovljević, K., Matić, I. Z., Stanojković, T., Krivokuća, A., Marković, V., Joksović, M. D., Joksović, L. Synthesis, antioxidant and antiproliferative activities of 1,3,4-thiadiazoles derived from phenolic acids. Bioorganic & Medicinal Chemistry Letters, (2017).27(16), 3709–3715.
  24. Jakovljević, K., Joksović, M. D., Botta, B., Jovanović, L. S., Avdović, E., Marković, Z., Marković, V. Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies. ComptesRendus. (2019). 22 585-598.
  25. Djukic, M., Fesatidou, M., Xenikakis, I., Geronikaki, A., Angelova, V. T., Savic, V.,Saso, L.In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole. Chemico-Biological Interactions, (2018).286, 119–131
  26. Sauer, A. C., Leal, J. G., Stefanello, S. T., Leite, M. T. B., Souza, M. B., Soares, F. A. A., Dornelles, L.. Synthesis and antioxidant properties of organosulfur and organoselenium compounds derived from 5-substituted-1,3,4-oxadiazole/thiadiazole-2-thiols. Tetrahedron Letters, (2017)58(1), 87–91.
  27. Fadda, A. A., Abdel-Latif, E., & El-Mekawy, R. E. Synthesis and molluscicidal activity of some new thiophene, thiadiazole and pyrazole derivatives. European Journal of Medicinal Chemistry, (2009).44(3), 1250–1256.
  28. El Shehry, M. F., Abu-Hashem, A. A., & El-Telbani, E. M. Synthesis of 3-((2,4-dichlorophenoxy)methyl)-1,2,4-triazolo(thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. European Journal of Medicinal Chemistry, (2010).45(5), 1906–1911.
  29. Lee, J., Lee, S.-H., Seo, H. J., Son, E.-J., Lee, S. H., Jung, M. E., Lee, J.Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: 1,3,4-Thiadiazolylmethylphenyl glucoside congeners. Bioorganic & Medicinal Chemistry, (2010)18(6), 2178–2194.
  30. Jatav, V., Mishra, P., Kashaw, S., & Stables, J. P. Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones. European Journal of Medicinal Chemistry, (2008). 43(1), 135–141.
  31. Harish, K. P., Mohana, K. N., &Mallesha, L. Synthesis of indazole substituted-1,3,4-thiadiazoles and their anticonvulsant activity. Drug Invention Today, (2013).5(2), 92–99.
  32. Rajak, H., Behera, C. K., Pawar, R. S., Singour, P. K., &Kharya, M. D. A novel series of 2,5-disubstituted 1,3,4-thiadiazoles as potential anticonvulsant agent. Chinese Chemical Letters, (2010).21(10), 1149–1152.
  33. Quintana, C., Klahn, A. H., Artigas, V., Fuentealba, M., Biot, C., Halloum, I., Arancibia, R. Cyrhetrenyl and ferrocenyl 1,3,4-thiadiazole derivatives: Synthesis, characterization, crystal structures and in vitro antitubercular activity. Inorganic Chemistry Communications, (2015). 55, 48–50
  34. Alegaon, S. G., Alagawadi, K. R., Sonkusare, P. V., Chaudhary, S. M., Dadwe, D. H., & Shah, A. S. Novel imidazo[2,1-b][1,3,4]thiadiazole carrying rhodanine-3-acetic acid as potential antitubercular agents. Bioorganic & Medicinal Chemistry Letters, (2012).22(5), 1917–1921.
  35. Yusuf, M., Khan, R. A., & Ahmed, B.. Syntheses and anti-depressant activity of 5-amino-1, 3, 4-thiadiazole-2-thiol imines and thiobenzyl derivatives.Bioorganic & Medicinal Chemistry, (2008) 16(17), 8029–8034.
  36. Zhang, K., Wang, P., Xuan, L.-N., Fu, X.-Y., Jing, F., Li, S., Chen, B.-Q. Synthesis and antitumor activities of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety. Bioorganic & Medicinal Chemistry Letters, (2014) 24(22), 5154–5156.
  37. Lv, M., Liu, G., Jia, M., &Xu, H.Synthesis of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold as insecticidal/acaricidal agents. Bioorganic Chemistry, (2018).81, 88–92
  38. Gomha, S., Edrees, M., Muhammad, Z., & El-Reedy, A.5-(Thiophen-2-yl)-1,3,4-thiadiazole derivatives: synthesis, molecular docking and in vitro cytotoxicity evaluation as potential anticancer agents. Drug Design, Development and Therapy, (2018)Volume 12, 1511–1523.
  39. Karolina Jasiak, AgnieszkaKudelko, Monika Wróblowska, Anna Biernasiuk, Anna Malm, and Maria Krawczyk. Convenient Synthesis and Biological Activity of Mono and Diacyl 2,5-Dimercapto-1,3,4-thiadiazole Derivatives. Journal of Heterocyclic Chemistry.2017.54(6) 3241-3249.
  40. JumatSalimon,NadiaSalih, EmadYousif, AyadHameed and HibaIbraheem. Synthesis, Characterization and Biological Activity of Schiff Bases of 2, 5-Dimercapto-1,3,4-thiadiazole . Australian Journal of Basic and Applied Sciences, 4(7): 2016-2021, 2010
  41. T. S. Zhivotova. Reaction of 1,3,4-thiadiazol-2,5-dithiolwith n-acryloyl-substitutedderivatives of several alkaloids. Chemistry of Natural Compounds, Vol. 45, No. 6, 2009.
  42. T. S. Zhivotova, A. M. Gazaliev, O. V. Dryuk, and A. Zh. Seitembetova. Synthesis and Antioxidant Activity of Alkaloid- andAmine-containing Salts of 1,3,4-Thiadiazole-2,5-disulfonic Acid. Russian Journal of Applied Chemistry, 2008, Vol. 81, No. 2, pp. 259-262.
  43. T. E. Glotova, A. S. Nakhmanovich, and T. N. Komarova, Khim. Geterotsikl.Soedin., 8, 1144 (1988).
  44. A. A. Katritskii, Physicochemical Methods in Chemistry of Heterocyclic Compounds [in Russian], Khimiya,Moscow, 1966, p. 59.
  45. L. J. Bellamy, Advances in Infrared Group Frequencies, Methuen, London, 1968.
  46. Gazaliev, A.M., Zhurinov, M.Zh., and Fazylov, S.D.,Novyebioaktivnyeproizvodnyealkaloidov(NewBioactive Alkaloid Derivatives), Alma-Ata: Gylym,1992.
  47. Levy, G.C,.and Nelson, G.L., Carbon-13 NuclearMagnetic Resonance for Organic Chemists, NewYork: Wiley, 1972.