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(E)-13-(4-Amino-phen-yl)parthenolide.

Narsimha Reddy Penthala1, Venumadhav Janganati1, Sean Parkin2

  • 1Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.

Acta Crystallographica. Section E, Structure Reports Online
|January 24, 2014
PubMed
Summary

A novel compound was synthesized from parthenolide and 4-iodo-aniline via Heck reaction. Its crystal structure reveals fused rings and intermolecular hydrogen bonding, confirmed by resonance scattering.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Medicinal Chemistry

Background:

  • Parthenolide is a natural product with known biological activities.
  • The Heck reaction is a versatile tool for carbon-carbon bond formation.

Purpose of the Study:

  • To synthesize and characterize a novel derivative of parthenolide.
  • To elucidate the crystal structure and intermolecular interactions of the new compound.

Main Methods:

  • Heck reaction for synthesis.
  • X-ray crystallography for structure determination.
  • Resonance scattering for absolute structure confirmation.

Main Results:

  • Successful synthesis of a C21H25NO3 compound, identified as the E-isomer.
  • Detailed structural analysis revealing fused ten-, five-, and three-membered rings with a 4-amino-phenyl substituent.
  • Crystal structure shows N-H⋯O hydrogen bonds forming chains and C-H⋯O interactions forming a 2D network.

Conclusions:

  • The study reports the synthesis and comprehensive structural characterization of a novel parthenolide derivative.
  • The crystal packing is dominated by hydrogen bonding and van der Waals forces.
  • The absolute configuration was unambiguously determined.