Moustafa Reem, Remete Attila Márió, Szakonyi Zsolt, Szemerédi Nikoletta, Spengler Gabriella, Le Tam Minh
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
Department of Medical Microbiology, Albert Szent-Györgyi Health Center and Albert Szent-Györgyi Medical School, University of Szeged, Semmelweis u. 6, H-6725 Szeged, Hungary.
Int J Mol Sci. 2025 May 16;26(10):4791. doi: 10.3390/ijms26104791.
A library of neoisopulegol-based amino and thiol adducts was developed from (+)-neoisopulegol, derived from commercially available (-)-isopulegol. Michael addition of different nucleophiles towards its highly active ,-unsaturated -lactone motif was accomplished, resulting in diverse amino and thiol analogs in stereoselective reactions. Then, the lactone ring was opened, with NH and benzylamine furnishing primary amide and -benzyl-substituted amide derivatives, respectively. The in vitro antimicrobial effect of prepared compounds was also explored. The results revealed that naphthylmethyl-substituted -aminolactone, the most promising compound, displayed selective inhibition for the Gram-positive bacteria with an MIC (minimum inhibitory concentration) value of 12.5 μM. A docking study was performed to interpret the obtained results.
以市售（-）-异胡薄荷醇衍生的（+）-新异胡薄荷醇为原料，构建了一个基于新异胡薄荷醇的氨基和硫醇加合物文库。通过将不同亲核试剂对其高活性的α,β-不饱和γ-内酯基序进行迈克尔加成反应，在立体选择性反应中得到了多种氨基和硫醇类似物。然后，打开内酯环，用氨和苄胺分别得到伯酰胺和α-苄基取代的酰胺衍生物。还探究了所制备化合物的体外抗菌效果。结果表明，最有前景的化合物萘甲基取代的α-氨基内酯对革兰氏阳性菌具有选择性抑制作用，其最低抑菌浓度（MIC）值为12.5 μM。进行了对接研究以解释所得结果。
