REGIOSELECTIVE N-ACYLATION OF 2-MERCATOBENZIMIDAZOLE: SYNTHESIS, THERMODYNAMIC STABILITY, AND TARGETED ANTIMICROBIAL MECHANISMS
Abstract
The targeted functionalization of ambident heterocyclic systems remains a highly challenging frontier in modern medicinal chemistry and molecular design [1]. Unlike soft alkylating agents that exhibit a high affinity for the exocyclic sulfur atom, hard acylating electrophiles introduce a unique competition between kinetic $S$-acylation and thermodynamic N-acylation pathways within the 2-mercaptobenzimidazole core [2]. Exploring this regioselective behavior is critical because introducing structurally diverse acyl groups onto the endocyclic nitrogen atom drastically alters the electronic density distribution of the imidazole ring. This structural shift not only creates a unique electrostatic profile but also improves the capability of the compound to form precise hydrogen bonds with key bacterial and fungal enzyme pockets [3, 4].
The primary objective of this investigation is to establish an optimized protocol for the regioselective N-acylation of 2-mercaptobenzimidazole using diverse aliphatic and aromatic acyl halides, evaluate the thermodynamic stability of the resulting scaffolds via spectral characterization, and assess their in vitro antimicrobial spectrum.
References
3.Yadav, P., & Ganguly, S. Synthesis, characterization, and biological significance of N-substituted benzimidazoles. Journal of Heterocyclic Chemistry, 52(3), 645–660, 2015.
4.Rasulev, B., Nazarov, A., & Akbarov, A. Electrostatic potentials and QSAR modeling of bioactive benzimidazole scaffolds. Chemistry of Heterocyclic Compounds, 51(7), 832–839, 2015.
5. Khabibullaev, S., Yuldashev, N., & Mamazulunov, N. (2023). Metabolic changes in the body as the result of long-term use of artificial sweetener-sodium cyclamate. Science and innovation, 2(D10), 64-70..
6. Қодиров, Р. Ш., Мамазулунов, Н. Х., Ботиров, Э. Х., & Юсупов, М. М. (2020). Флавоноиды russowia sogdiana (BGE). fedsch. Экономика и социум, (12-1), 628-631.
7. Мамазулунов, Н. (2021). Послеоперационные острые эрозии и язвы и их клинико-биохимичесий прогноз. Экономика и социум, (3-2 (82)), 116-119.
8. Nurmuhammad, M. (2025). Buyraklarda urat toshlari hosil bo ‘lishi va davolash yo ‘llari. Ta'lim innovatsiyasi va integratsiyasi, 59(3), 90-94.
9. Mamazulunov, N. (2021). Inorganic phosphate and principles of fluorescence. Экономика и социум, (3-1 (82)), 167-169.
10. Мамазулунов, Н. Х., Ботиров, Э. Х., & Юсупов, М. М. (2020). Флавоноиды russowia sogdiana (BGE). fedsch. Экономика и социум, (12 (79)), 628-631.
11. Bokiyev, M., & Mamazulunov, N. (2020). Some biological active products of metallocenes. Экономика и социум, (12 (79)), 67-70.
12. Икрамова, М. М., Таджибоев, К. Т., & Мамазулунов, Н. Х. (2013). Определение активности аминотрансфераза в перфузате печени при экспериментальном токсическом гепатите. science and world, 42.
13. Юлдашев, Н., Мамазулунов, Н., & Хабибуллаев, С. Научное обозрение. Биологические науки. Научное обозрение, (2), 51-57.
14. Mamazulunov, N. Maqola NamDU Ilmiy Axborotnoma 2024 10 son.
