Discovery of 3-hydroxymethyl-azetidine derivatives as potent polymerase theta inhibitors

Bioorg Med Chem. 2024 Apr 1:103:117662. doi: 10.1016/j.bmc.2024.117662. Epub 2024 Mar 6.

Abstract

Inhibition of the low fidelity DNA polymerase Theta (Polθ) is emerging as an attractive, synthetic-lethal antitumor strategy in BRCA-deficient tumors. Here we report the AI-enabled development of 3-hydroxymethyl-azetidine derivatives as a novel class of Polθ inhibitors featuring central scaffolding rings. Structure-based drug design first identified A7 as a lead compound, which was further optimized to the more potent derivative B3 and the metabolically stable deuterated compound C1. C1 exhibited significant antiproliferative properties in DNA repair-compromised cells and demonstrated favorable pharmacokinetics, showcasing that 3-hydroxymethyl-azetidine is an effective bio-isostere of pyrrolidin-3-ol and emphasizing the potential of AI in medicinal chemistry for precise molecular modifications.

MeSH terms

  • Azetidines* / chemistry
  • DNA Repair
  • Humans
  • Neoplasms*

Substances

  • Azetidines