The Application of Bicyclo[1.1.1]pentane as a Bioisostere of the Phenyl Ring in Pharmaceutical Chemistry

Zhuohan Fang; Qian Xu; Xuehe Lu; Nianfeng Wan; Wu-Lin Yang

doi:10.1055/s-0043-1775395

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(06): 1171-1179
DOI: 10.1055/s-0043-1775395

short review

Bioisosteres

The Application of Bicyclo[1.1.1]pentane as a Bioisostere of the Phenyl Ring in Pharmaceutical Chemistry

Zhuohan Fang‡

^aShanghai Key Laboratory of Chemical Biology & School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China

,

Qian Xu‡

^aShanghai Key Laboratory of Chemical Biology & School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China

,

Xuehe Lu∗

^bFrontiers Science Center for Transformative Molecules, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, 429 Zhangheng Lu, Shanghai 200444, P. R. of China

,

Nianfeng Wan

^aShanghai Key Laboratory of Chemical Biology & School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China

,

Wu-Lin Yang∗

^aShanghai Key Laboratory of Chemical Biology & School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China

› Institutsangaben

Abstract

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Abstract

Bicyclo[1.1.1]pentane (BCP) is a bridging ring skeleton with three-dimensional structure. BCP is a bioisostere of the phenyl ring, tert-butyl group, and alkynes; it has excellent physical and chemical properties compared with phenyl ring, so it has been widely considered by the pharmaceutical chemistry. This short review examines related reports of BCP as a bioisostere of the phenyl ring, and the changes in physicochemical properties and biological activity after substitution. The solubility, clogP, and metabolic toxicity of the drug are improved by BCP bioisosteres, but the biological activity of BCP is lower than the phenyl ring. The application of BCP in drug research and development will be further expanded to provide more possibilities for future drug innovation and development.

1 Introduction

2 Replacement of Phenyl Rings by BCP

3 Conclusion

Key words

bicyclo[1.1.1]pentane - phenyl ring - bioisosteres - physicochemical properties - pharmaceutical chemistry

Volltext

Referenzen

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