Metal-Free Catalyzed Oxidation/Decarboxylative [3+2] Cycloaddition Sequences of 3-Formylchromones to Access Pyrroles with Anti-Cancer Activity

Molecules. 2023 Nov 15;28(22):7602. doi: 10.3390/molecules28227602.

Abstract

An efficient and direct approach to pyrroles was successfully developed by employing 3-formylchromones as decarboxylative coupling partners, and facilitated by microwave irradiation. The protocol utilizes easily accessible feedstocks, a catalytic amount of DBU without any metals, resulting in high efficiency and regioselectivity. Notably, all synthesized products were evaluated against five different cancer cell lines and compound 3l selectively inhibited the proliferation of HCT116 cells with an IC50 value of 10.65 μM.

Keywords: 3-formylchromones; anti-cancer activity; decarboxylation; metal-free; pyrroles.

MeSH terms

  • Catalysis
  • Cycloaddition Reaction
  • Metals*
  • Pyrroles* / pharmacology

Substances

  • Pyrroles
  • formylchromone
  • Metals

Grants and funding

This research was founded by the Science and Technology Research Program of Chongqing Municipal Education Commission (KJQN202301349, KJQN202201302, KJQN202101340, and KJZD-M201801301), the Natural Science Foundation Project of CQ CSTSC (cstc2021ycjh-bgzxm0163, cstc2020jcyj-msxmX0849, and cstc2021jcyj-bshX0242), and the Chongqing University of Arts and Sciences: Program for Talents Introduction (R2022YX07, R2021FYX05, and P2022YX10).