N-[2-[2-(4-Phenylbutyl)benzofuran-4-yl]cyclopropylmethyl]acetamide: an orally bioavailable melatonin receptor agonist

Bioorg Med Chem Lett. 2004 Oct 18;14(20):5157-60. doi: 10.1016/j.bmcl.2004.07.055.

Abstract

N-[2-[2-(4-Phenylbutyl)benzofuran-4-yl]cyclopropylmethyl]acetamide 3a was synthesized as an orally bioavailable agonist at MT1 and MT2 melatonin receptors with significantly low vasoconstrictive activity.

Publication types

  • Comparative Study

MeSH terms

  • Acetamides / chemical synthesis
  • Acetamides / pharmacokinetics*
  • Acetamides / toxicity
  • Administration, Oral
  • Animals
  • Benzofurans / chemical synthesis
  • Benzofurans / pharmacokinetics*
  • Benzofurans / toxicity
  • Biological Availability
  • Cyclic AMP / antagonists & inhibitors
  • Cyclic AMP / biosynthesis
  • Dose-Response Relationship, Drug
  • Humans
  • In Vitro Techniques
  • Mice
  • Muscle Contraction / drug effects
  • Muscle, Smooth, Vascular / drug effects
  • Muscle, Smooth, Vascular / physiology
  • NIH 3T3 Cells
  • Radioligand Assay
  • Rats
  • Receptor, Melatonin, MT1 / agonists*
  • Receptor, Melatonin, MT2 / agonists*
  • Structure-Activity Relationship

Substances

  • Acetamides
  • Benzofurans
  • N-(2-(2-(4-phenylbutyl)benzofuran-4-yl)cyclopropylmethyl)acetamide
  • Receptor, Melatonin, MT1
  • Receptor, Melatonin, MT2
  • Cyclic AMP