Preparation, Purification and Spectral Properties of A New Thiourea Derivative Produced from Γ-Aminomycic Acid with A Thiourea Fragment of P-Hydroxybenzoic Acid
Downloads
The article describes the synthesis of a new 1-(4-hydroxybenzoyl)-3-(3-carboxypropyl)thiourea by nucleophilic addition reaction between 4-hydroxybenzoyl isothiocyanate and γ-aminobutyric acid (GABA), the optimization of reaction conditions, the isolation and purification of the product, as well as its physicochemical and spectral characterization. The reaction was found to proceed in dimethylformamide or ethanol, in an inert (argon) environment, in the temperature range of 20-50 °C, without a catalyst or in the presence of a small amount of triethylamine, for 1-3 hours with a yield of 80.4%. The resulting compound is considered an important precursor in the development of penicillin analogues to overcome the instability of the β-lactam ring and resistance to β-lactamases, as well as in the synthesis of ligands for GABA-A and GABA-B receptors. This work proposes a simple, inexpensive, and industrially applicable method for synthesizing hybrid molecules based on thiourea.
A. Said, “Tiourea derivatives biological application: detailed review,” Chemistry Materials, no. 6(3), p. 25, 2024.
S. N. Pandeya, “Acetophenone semicarbazone thiourea derivatives anticonvulsant activity,” Pharmacological Research, vol. 37, no. 1, pp. 17–22, 1998.
R. J. Nevagi, “Strong antiangiogenic activity of benzodioxole-containing thiourea derivatives: synthesis and anticancer activity,” European Journal of Medicinal Chemistry, vol. 199, p. 112333, 2020.
B. Niaz, “Thiourea derivatives: antifungal and antioxidant activity against plant pathogens,” PubMed, 2025.
B. Song, “Thiourea derivatives: design, synthesis, antiviral activity and SAR studies,” Journal of Agricultural and Food Chemistry, vol. 63, no. 5, pp. 1370–1377, 2015.
World Health Organization, “New report on antimicrobial resistance crisis and urgent measures,” WHO News, 2019.
ACS Infectious Diseases, “β-lactamase mediated antibiotic resistance and inhibitor solutions,” ACS Infectious Diseases, vol. 4, no. 9, pp. 1406–1416, 2018.
H. Hikino, “p-Hydroxythiobenzamides synthesis and reactions,” ARKIVOC, no. 9, pp. 247–252, 1994.
A. K. Brel et al., “O-aminoacyl derivatives of hydroxybenzoic acids and evaluation of biological activity,” Bulletin of Volgograd Technical University, no. 5(276), p. 48, 2023.
A. K. Brel, Y. N. Budaeva, S. V. Lisina, and L. N. Niyazov, “Synthesis of amides of hydroxybenzoic acid derivatives with 6-amino-1,3-dimethylpyrimidine-2,4-dione,” Bulletin of the Volgograd State Technical University, no. 12(271), pp. 66–69, 2022.
L. J. Bellamy and P. E. Rogasch, “C=S stretching in the infrared frequency and −N−C=S bands,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 1989.
D. H. Rose and J. W. Gravel, “Universal Design for Learning,” in International Encyclopedia of Education, 3rd ed., Elsevier, 2010, pp. 119–124.
CAST, “Universal Design for Learning Guidelines version 2.2,” Wakefield, MA, USA: CAST, 2018.
R. E. Mayer, Multimedia Learning, 2nd ed. Cambridge, UK: Cambridge University Press, 2009.
C. S. Dweck, Mindset: The New Psychology of Success. New York, NY, USA: Random House, 2006.
