Singh Nasseb, Abrol Vidushi, Parihar Sarita, Kumar Satish, Khanum Ghazala, Mir Jan Mohammad, Dar Alamgir Ahmad, Jaglan Sundeep, Sillanpää Mika, Al-Farraj Saleh
Synthetic Organic Chemistry Laboratory, School of Biotechnology, Faculty of Sciences, Shri Mata Vaishno Devi University, Katra, Jammu & Kashmir 182320, India.
Department of Chemistry, Govt. Degree College Udhampur, Jammu and Kashmir 182101, India.
ACS Omega. 2023 Oct 27;8(44):41960-41968. doi: 10.1021/acsomega.3c07315. eCollection 2023 Nov 7.
In the present study, a series of benzotriazole-based β-amino alcohols were efficiently synthesized in excellent yields via aminolysis of benzotriazolated epoxides under catalyst- and solvent-free conditions. Further these β-amino alcohols were successfully utilized to synthesize the corresponding benzotriazole-based oxazolidine heterocyclic derivatives. All the synthesized compounds were characterized by various spectroscopic techniques such as H NMR, C NMR, and mass spectroscopy for structure elucidation. The compounds were subjected to a microtiter plate-based antimicrobial assay. The antimicrobial activity results reveal that the compounds , , and were found to be active against (ATCC-25923) with minimum inhibitory concentrations (MICs) of 32, 8, and 64 μM, respectively. Also, the compounds , , , , , , , , , , , and showed effective activity against (ATCC 6633) with MICs of 64, 16, 16, 16, 64, 16, 64, 64, 32, 64, 8, and 16 μM, respectively. A biological investigation was conducted, including molecular docking of two compounds with several receptors to identify and confirm the best ligand-protein interactions. Hence, this study found a significant strategy to diversify the chemical molecules. The synthesized compounds play a potential role as an antibacterial intensifier against some pathogenic bacteria for the development of antibacterial substances.
在本研究中，通过苯并三唑化环氧化物在无催化剂和无溶剂条件下的氨解反应，高效合成了一系列基于苯并三唑的β-氨基醇，产率优异。进一步地，这些β-氨基醇被成功用于合成相应的基于苯并三唑的恶唑烷杂环衍生物。所有合成的化合物通过各种光谱技术如¹H NMR、¹³C NMR和质谱进行表征以阐明结构。这些化合物进行了基于微量滴定板的抗菌测定。抗菌活性结果表明，化合物、和对金黄色葡萄球菌（ATCC - 25923）有活性，最小抑菌浓度（MICs）分别为32、8和64 μM。此外，化合物、、、、、、、、、、和对白色念珠菌（ATCC 6633）显示出有效活性，MICs分别为64、16、16、16、64、16、64、64、32、64、8和16 μM。进行了生物学研究，包括两种化合物与几种受体的分子对接，以识别和确认最佳的配体 - 蛋白质相互作用。因此，本研究发现了一种使化学分子多样化的重要策略。合成的化合物在开发抗菌物质方面作为针对某些病原菌的抗菌增强剂发挥潜在作用。
