Derivatization of Marine‐Derived Fascaplysin via Highly Regioselective Suzuki‐Miyaura Coupling Contributing to the Enhanced Antibacterial Activity. Issue 27 (14th July 2022)

• Record Type: Journal Article
• Authors: Jiang, Yinli; Qiu, Hongda; Liang, Weida; Lin, Junhao; Lin, Jiayu; Liu, Wan; Wang, Xiao; Cui, Wei; Chen, Xiaowei; Wang, Huifei; Zhao, Lingling; Liang, Hongze
• Is Part Of: ChemistrySelect. Volume 7:Issue 27(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-07-14
• Subjects: Antibacterial activity -- Alkaloids -- Drug design -- Fascaplysin -- Selective Suzuki-Miyaura coupling; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202201441
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A new methodology for the synthesis of fascaplysin derivatives has been established. A library of diversified fascaplysins can be efficiently and quickly prepared by regioselective Suzuki‐Miyaura coupling and subsequent quaternization for the first time. The minimum inhibitory concentration assessment showed that the unique 5‐ring coplanar aromatic system plays a key role in the resulting bioactivity, and functional groups at different substitution position exert differentiable impact on the bactericidal activity. some synthesized fascaplysin derivatives exhibited higher antibacterial activities than the pristine fascaplysin and the positive controls, especially against Gram‐negative bacteria Escherichia coli (ATCC 25922). These novel fascaplysin derivatives may have promising application potentials as bactericidal drugs. Abstract : Novel fascaplysin derivatives have been synthesized via Suzuki‐Miyaura coupling with high regioselectivity, efficiency and simpleness. These derivatives exhibit potent antibacterial activity, especially against Gram‐negative bacterial Escherichia coli (ATCC 25922).