Gold(I)-Catalyzed Intramolecular Hydrothiophenylation of N-Thiophen-3-yl Alkynylamides for Accessing Thieno[3,2- b]pyridine-5(4 H)-ones: Development of F-Actin Specific Fluorescent Probes

J Org Chem. 2022 Apr 1;87(7):4936-4950. doi: 10.1021/acs.joc.1c02923. Epub 2022 Feb 11.

Abstract

Herein, we describe an original synthetic method for a series of fluorescent thieno[3,2-b]pyridine-5(4H)-one derivatives prepared via the gold(I)-catalyzed 6-endo-dig intramolecular hydrothiophenylation process involving N-thiophen-3-yl alkynylamides. The brightness was improved; emission could be tuned, and larger Stokes shifts were recorded. We also designed and synthesized the phalloidin-based fluorescent chemical probes KF-P1 and KF-P2 to realize fluorescent F-actin imaging.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actins
  • Catalysis
  • Fluorescent Dyes* / chemistry
  • Gold
  • Pyridines / chemistry
  • Thiophenes*

Substances

  • Actins
  • Fluorescent Dyes
  • Pyridines
  • Thiophenes
  • Gold