Hydrazinonaphthalene and azonaphthalene thrombopoietin mimics are nonpeptidyl promoters of megakaryocytopoiesis

  • J Med Chem. 2001 Oct 25;44(22):3730-45. doi: 10.1021/jm010283l.
K J Duffy  1 ,  M G Darcy ,  E Delorme ,  S B Dillon ,  D F Eppley ,  C Erickson-Miller ,  L Giampa ,  C B Hopson ,  Y Huang ,  R M Keenan ,  P Lamb ,  L Leong ,  N Liu ,  S G Miller ,  A T Price ,  J Rosen ,  R Shah ,  T N Shaw ,  H Smith ,  K C Stark ,  S S Tian ,  C Tyree ,  K J Wiggall ,  L Zhang ,  J I Luengo
Affiliations
  • 1. GlaxoSmithKline, 1250 South Collegeville Road, Collegeville, PA 19426, USA. [email protected]
Abstract

High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalenesulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC(50) values in the region of 1-20 nM.