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Mono-cyclopentyl substituted [1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties

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Pages 378-394 | Received 28 Aug 2023, Accepted 29 Dec 2023, Published online: 10 Jan 2024

References

  • Hu Y, Li CY, Wang XM, et al. 1,3,4-Thiadiazole: synthesis, reactions, and applications in medicinal, agricultural, and materials chemistry. Chem Rev. 2014;114:5572–5610. doi:10.1021/cr400131u
  • Li Y, Geng J, Liu Y, et al. Thiadiazole—a promising structure in medicinal chemistry. ChemMedChem. 2013;8:27–41. doi:10.1002/cmdc.201200355
  • Sahraei A, Kargar H, Hakimi M, et al. Synthesis, characterization, crystal structures and biological activities of eight-coordinate zirconium(IV) Schiff base complexes. Transit Met Chem. 2017;42:483–489. doi:10.1007/s11243-017-0152-x
  • Visagaperumal D, Ramalingam J, Chandy V. 1, 3, 4-thiadiazoles: an overview. Curr Res Bioorg Org Chem. 2018: CRBOC-103. doi:10.29011/CRBOC-101.100003
  • Anthwal T, Paliwal S, Nain S. Diverse biological activities of 1,3,4-thiadiazole Scaffold. Chemistry. 2022;4:1654–1671. doi:10.3390/chemistry4040107
  • Chen J, Yi C, Wang S, et al. Novel amide derivatives containing 1,3,4-thiadiazole moiety: design, synthesis, nematocidal and antibacterial activities. Bioorg Med Chem Lett. 2019;29:1203–1210. doi:10.1016/j.bmcl.2019.03.017
  • Mistry JK, Dawes R, Choudhury A, et al. 5-Mercapto-1,3,4-thiadiazole-2(3H)-thione: synthesis and structure of alkylated derivatives. J Heterocycl Chem. 2014;51:747–754. doi:10.1002/jhet.1903
  • Bats JW. The crystal structure of 2,5-dimercaptothiadiazole. Acta Crystallogr Sect B: Struct Crystallogr Cryst Chem. 1976;32:2866–2870. doi:10.1107/S0567740876009059
  • Ong CL, Jiang X, Juan JC, et al. Ashless and non-corrosive disulfide compounds as excellent extreme pressure additives in naphthenic oil. J Mol Liq. 2022;351:118553. doi:10.1016/j.molliq.2022.118553
  • Ong CL, Heidelberg T, Juan JC, et al. Metal-free and green synthesis of a series of new bis(2-alkylsulfanyl-[1,3,4]thiadiazolyl)-5,5′-disulfides and 2,2′-Dibenzothiazyl disulfide via oxidative self-coupling using hydrogen peroxide. Polyhedron. 2022;213:115610. doi:10.1016/j.poly.2021.115610
  • Ong CL, Heidelberg T, Juan JC, et al. Practical and efficient recyclable oxidative system for the preparation of symmetrical disulfides under aerobic conditions. J Sulfur Chem. 2021;42:281–294. doi:10.1080/17415993.2020.1856849
  • Gorjian H, Khaligh NG. 3,4-Dichloro-1,2,5-thiadiazole: a commercially available electrophilic sulfur transfer agent and safe resource of ethanedinitrile. J Sulfur Chem. 2022;43:169–179. doi:10.1080/17415993.2021.1991928
  • Abdul Basir NF, Gorjian H, Johan MR, et al. Synthesis and characterization of two new 2,5-bis-cycloalkylsulfanyl-[1,3,4]thiadiazoles and study of the crystal structure, thermal behavior, and biological activities compared with bismuthiol. J Mol Struct. 2023;1281:135087. doi:10.1016/j.molstruc.2023.135087
  • Hayashi Y. Pot economy and one-pot synthesis. Chem Sci. 2016;7:866–880. doi:10.1039/c5sc02913a
  • Esmaiel MH, Basuony HA, Al-Nawasany MK, et al. Thiadiazole-2-thiol-5-thione and 2,5-dimercapto-1,3,4-thiadiazol tautomerism, conformational stability, vibrational assignments, inhibitor efficiency and quantum chemical calculations. Z Phys Chem. 2020;234:415–440. doi:10.1515/zpch-2018-1346
  • Lin-Vien D, Colthup NB, Fateley WG, et al. The handbook of infrared and Raman characteristic frequencies of organic molecules. San Diego: Academic Press; 1981.
  • Colthup NB, Daly LH, Wiberley SE. Introduction to infrared and Raman spectroscopy. New York: Elsevier Science, Academic Press; 1990.
  • Rao CNR, Venkataraghavan R. The C=S stretching frequency and the “-N-C=S bands” in the infrared. Spectrochim Acta. 1962;18:541–547. doi:10.1016/S0371-1951(62)80164-7
  • Allen FH, Kennard O, Watson DG, et al. Tables of bond lengths determined by X-ray and neutron diffraction. Part I. Bond lengths in organic compounds. J Chem Soc Perkin Trans. 1987;2:S1–S19. doi:10.1039/p298700000s1
  • Saeed A, Ashraf Z, Nadeem H, et al. An investigation of supramolecular synthons in 1,2,4-triazole-3(4H)-thione compounds. X-ray crystal structures, energetic and hirshfeld surface analysis. J Mol Struct. 2019;1195:796–806. doi:10.1016/j.molstruc.2019.06.049
  • Hameed A, Shafiq Z, Yaqub M, et al. Robustness of a thioamide {···H-N-C = S}2 synthon: synthesis and the effect of substituents on the formation of layered to cage-like supramolecular networks in coumarinthiosemicarbazone hybrids. New J Chem. 2015;39:6052–6061. doi:10.1039/C5NJ00734H
  • Saeed A, Florke U, Fantoni A, et al. Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives. CrystEngComm. 2017;19:1495–1508. doi:10.1039/C6CE02619B
  • https://instanano.com/characterization/calculator/xrd/crystallite-size/
  • https://instanano.com/characterization/calculator/xrd/d-value/
  • Küçükgüzel ŞG, Çıkla-Süzgün P. Recent advances bioactive 1,2,4-triazole-3-thiones. Eur J Med Chem. 2015;97:830–870. doi:10.1016/j.ejmech.2014.11.033
  • Qi L, Wu S-J, Li M-C, et al. Synthesis, biological activity, and molecular docking studies of novel 5-substituted-1,2,4-triazole-3-thione derivatives. ChemistrySelect. 2020;5:2015–2022. doi:10.1002/slct.201904418
  • Aouad MR, Khan DJO, Said MA, et al. Novel 1,2,3-triazole derivatives as potential inhibitors against covid-19 main protease: synthesis, characterization, molecular docking and DFT studies. ChemistrySelect. 2021;6:3468–3486. doi:10.1002/slct.202100522
  • Mahran AM, Hassan NA. A one-step synthesis and antimicrobial activities of new substituted dihydro-1,3,4-thiadiazoles. Arch Pharm Res. 2006;29:46–49. doi:10.1007/BF02977467
  • Azam F, Madi AM, Ali HI. Molecular docking and prediction of pharmacokinetic properties of dual mechanism drugs that block MAO-B and adenosine A2A receptors for the treatment of Parkinson's disease. J Young Pharm. 2012;4:184–192. doi:10.4103/0975-1483.100027

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