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

Basir, Nurul Fatimah Abdul and Gorjian, Hayedeh and Johan, Mohd Rafie and Khaligh, Nader Ghaffari (2023) 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. Journal of Molecular Structure, 1281. ISSN 0022-2860, DOI https://doi.org/10.1016/j.molstruc.2023.135087.

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Abstract

Two new derivatives of 2,5-bis-cycloalkylsulfanyl-1,3,4]thiadiazoles, i.e., 2,5-bis-cyclopentylsulfanyl-1,3,4]thiadiazole and 2,5-bis-cyclohexylsulfanyl-1,3,4]thiadiazole, were synthesized for a first time through a one-pot two-step procedure through the nucleophilic substitution of the potassium salt of 1,3,4-thiadiazole-2,5-dithiolate with chlorocyclopentane or bromocyclohexane in ethanol under reflux conditions. A cost-effective work-up was applied for the separation and purification of desired products. The products were characterized by physical and spectroscopic techniques. The long colorless needle-like crystals of 2,5-bis-cyclohexylsulfanyl-1,3,4]thiadiazole were obtained, and its crystal structure was stud-ied by single-crystal X-ray diffraction analysis. The transition phases and thermal stability of bismuthiol and two new bis-cycloalkyl bismuthiol were investigated by TGA/DTG and DSC. The thermal decomposi-tion of bismuthiol was reported in the literature; herein, a detailed of its thermal behavior is analyzed for the first time. Finally, the biological activity of bismuthiol and two new bis-cyclopentylsulfanyl and bis-cyclohexylsulfanyl substituted bismuthiol derivatives were screened in vitro against the gram-negative (Escherichia coli ATCC 25922) and gram-positive (Staphylococcus aureus ATCC 25923) bacterial species by the disk diffusion method.(c) 2023 Elsevier B.V. All rights reserved.

Item Type: Article
Funders: Universiti Malaya, Malaysia (ST018-2022) ; (IIRG004A-2022FNW)
Uncontrolled Keywords: Heterocycles; Crystal structure; Nanostructures; Thermal behavior; Biological activity
Subjects: Q Science > QD Chemistry
Divisions: Deputy Vice Chancellor (Research & Innovation) Office > Nanotechnology & Catalysis Research Centre
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 21 Jul 2025 02:31
Last Modified: 21 Jul 2025 02:31
URI: http://eprints.um.edu.my/id/eprint/50891

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