Structure-activity relationships of 2-pyrimidinecarbohydrazides as utrophin modulators for the potential treatment of Duchenne muscular dystrophy

Bioorg Med Chem. 2022 Sep 1:69:116812. doi: 10.1016/j.bmc.2022.116812. Epub 2022 May 18.

Abstract

A therapeutic approach that holds the potential to treat all Duchenne muscular dystrophy (DMD) patient populations is utrophin modulation. Ezutromid, a first generation utrophin modulator which was later found to act via antagonism of the arylhydrocarbon receptor, progressed to Phase 2 clinical trials. Although interim data showed target engagement and functional improvements, ezutromid ultimately failed to meet its clinical endpoints. We recently described the identification of a new class of hydrazide utrophin modulators which has a different mechanism of action to ezutromid. In this study we report our early optimisation studies on this hydrazide series. The new analogues had significantly improved potency in cell-based assays, increased sp3 character and reduced lipophilicity, which also improved their physicochemical properties. A representative new analogue combining these attributes increased utrophin protein in dystrophic mouse cells showing it can be used as a chemical tool to reveal new insights regarding utrophin upregulation as a strategy for DMD therapeutic intervention.

Keywords: Carbohydrazide; Duchenne muscular dystrophy; LUmdx; Phenotypic screening; Utrophin modulator.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Hydrazines / pharmacology
  • Hydrazines / therapeutic use
  • Mice
  • Muscle, Skeletal / metabolism
  • Muscular Dystrophy, Duchenne* / drug therapy
  • Muscular Dystrophy, Duchenne* / metabolism
  • Structure-Activity Relationship
  • Up-Regulation
  • Utrophin / genetics
  • Utrophin / metabolism
  • Utrophin / therapeutic use

Substances

  • Hydrazines
  • Utrophin