Structure-Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells

J Med Chem. 2017 Nov 22;60(22):9275-9289. doi: 10.1021/acs.jmedchem.7b01228. Epub 2017 Nov 3.

Abstract

Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple negative breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or overexpression of HER2. Gene expression profiling of TNBC has identified molecular subtypes and representative cell lines. An extract of the Texas native plant Amyris texana was found to have selective activity against MDA-MB-453 cells, a model of the luminal androgen receptor (LAR) subtype of TNBC. Bioassay-guided fractionation identified two oxazole natural products with selective activity against this cell line. Conducted analog synthesis and structure-activity relationship studies provided analogs with more potent and selective activity against two LAR subtype cell line models, culminating in the discovery of compound 30 (CIDD-0067106). Lead compounds discovered have potent and selective antiproliferative activities, and mechanisms of action studies show they inhibit the activity of the mTORC1 pathway.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Cycle / drug effects
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Imidazoles / chemical synthesis
  • Imidazoles / isolation & purification
  • Imidazoles / pharmacology*
  • Mechanistic Target of Rapamycin Complex 1 / metabolism
  • Oxazoles / chemical synthesis
  • Oxazoles / isolation & purification
  • Oxazoles / pharmacology*
  • Proline / analogs & derivatives*
  • Proline / chemical synthesis
  • Proline / isolation & purification
  • Proline / pharmacology
  • Proto-Oncogene Proteins c-akt / metabolism
  • Receptors, Androgen / metabolism*
  • Rutaceae / chemistry
  • Signal Transduction / drug effects
  • Structure-Activity Relationship
  • Triple Negative Breast Neoplasms / drug therapy*
  • Triple Negative Breast Neoplasms / metabolism

Substances

  • Antineoplastic Agents
  • CIDD-0067106
  • Imidazoles
  • Oxazoles
  • Receptors, Androgen
  • Proline
  • Mechanistic Target of Rapamycin Complex 1
  • Proto-Oncogene Proteins c-akt