Petrova Anastasiya V, Kazakova Oxana B
Ufa Institute of Chemistry, Ufa Federal Research Centre, Russian Academy of Science, 69, Prospect Octyabrya, Ufa 450054, Russia.
Int J Mol Sci. 2025 May 2;26(9):4329. doi: 10.3390/ijms26094329.
Nitrogen-containing substitutes, such as 1,2,3-triazoles and Mannich bases, are major pharmacophore systems, among others. The presented review summarizes the recent advances (2019-2024) in the synthesis of 1,2,3-triazoles and Mannich bases conjugated with a triterpenic core. These structural modifications have proven to be effective strategies for modulating the biological activity of triterpenes, with particular emphasis on antitumor and antiviral properties. Recent efforts in expanding the structural diversity of triazoles through A-ring modifications and C28 (or C30) substitutions are discussed. Notably, the first examples of N-alkylation of indole triterpenoids by propargyl bromide are presented, along with the application of propargylamine in the synthesis of rare triterpenic aldimines. The review also covers an application of triterpene alkynes in Mannich base synthesis, focusing on functionalization at various positions, including C28 and C19 of the lupane platform, and incorporating of amino acid spacers. While significant progress has been made both in synthetic strategies and pharmacological applications, further research is needed to fully explore the antibacterial, anti-inflammatory, and antidiabetic potential. The review will be useful to researchers in the fields of organic synthesis, natural product and medicinal chemistry, and pharmacology.
含氮取代基，如1,2,3-三唑和曼尼希碱等，是主要的药效基团系统。本综述总结了2019年至2024年期间与三萜核心共轭的1,2,3-三唑和曼尼希碱合成方面的最新进展。这些结构修饰已被证明是调节三萜生物活性的有效策略，尤其着重于抗肿瘤和抗病毒特性。文中讨论了通过A环修饰和C28（或C30）取代来扩大三唑结构多样性的最新研究成果。值得注意的是，展示了用炔丙基溴对吲哚三萜进行N-烷基化的首个实例，以及炔丙胺在合成罕见三萜醛亚胺中的应用。该综述还涵盖了三萜炔烃在曼尼希碱合成中的应用，重点关注在不同位置的官能化，包括羽扇豆烷平台的C28和C19位，以及引入氨基酸间隔基。虽然在合成策略和药理应用方面都取得了显著进展，但仍需要进一步研究以充分探索其抗菌、抗炎和抗糖尿病潜力。本综述对有机合成、天然产物与药物化学以及药理学领域的研究人员将有所帮助。
