Fujii Shinya
Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University.
Yakugaku Zasshi. 2022;142(2):131-137. doi: 10.1248/yakushi.21-00173-1.
Almost all conventional drug discovery research has been based on hydrocarbon-based frameworks and common chemical elements such as nitrogen, oxygen, sulfur, and the halogens. However, triggered by the approval of bortezomib, a boronic acid-containing pharmaceutical agent, the incorporation of functionalities that are not native in biological systems has been intensively investigated. Several other boron-containing pharmaceuticals have also been marketed. Therefore, the inclusion of various elements is one of the most promising strategies for the development of novel and distinctive drug candidates. In this symposium review, the author focused on the 'elements chemistry' approaches for the structural development of biologically active compounds, particularly those involving silicon and phosphorus. The isosteric exchange of Si and C (Si/C-exchange) is one of the most-investigated forms of substituting elements. We revealed the detailed physicochemical impact of Si/C-exchange, and we proposed several applications of silyl functionalities other than the simple Si/C-exchange. Regarding phosphorus, we recently revealed that the P-B substructure can function as the isostere of C-C or Si-C substructures. In addition to these isosteric exchanges, the development of biologically active compounds bearing unique substructures such as carboranes, hydrophobic boron clusters, and ferrocene is introduced. These novel strategies provide several options for structural development, offering great potential for expanding the chemical space of medicinal chemistry.
几乎所有传统的药物发现研究都基于碳氢化合物骨架以及常见化学元素,如氮、氧、硫和卤素。然而,在含硼酸药物硼替佐米获批的推动下,对生物系统中非天然官能团的引入展开了深入研究。其他几种含硼药物也已上市。因此,纳入各种元素是开发新型独特候选药物最具前景的策略之一。在本次专题综述中,作者重点关注了用于生物活性化合物结构开发的“元素化学”方法,特别是涉及硅和磷的方法。硅与碳的等排体交换(Si/C交换)是研究最多的元素取代形式之一。我们揭示了Si/C交换详细的物理化学影响,并提出了除简单Si/C交换之外硅烷基官能团的几种应用。关于磷,我们最近发现P-B子结构可作为C-C或Si-C子结构的等排体。除了这些等排体交换,还介绍了带有独特子结构(如碳硼烷、疏水硼簇和二茂铁)的生物活性化合物的开发。这些新策略为结构开发提供了多种选择,为拓展药物化学的化学空间提供了巨大潜力。