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
Document Type
Article
Publication Date
6-1-2023
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.
Keywords
Heterocycles, Crystal structure, Nanostructures, Thermal behavior, Biological activity
Divisions
nanotechnology
Funders
Universiti Malaya, Malaysia (ST018-2022) ; (IIRG004A-2022FNW)
Publication Title
Journal of Molecular Structure
Volume
1281
Publisher
Elsevier
Publisher Location
RADARWEG 29, 1043 NX AMSTERDAM, NETHERLANDS