The macrocyclic diarylether heptanoid (MDEH) natural products have been used in folk medicine for centuries. MDEHs are reported to exert anti-tumor properties by inhibiting the activation of NF-κB. Here we report the synthesis of a small MDEH library (first reported synthesis of racemic platycarynol) using a Grubbs cross metathesis/Ullmann cyclization strategy. Evaluation of the library led to the identification of MDEH 9b which sensitizes pancreatic cancer cells to gemcitabine mediated growth inhibition and apoptosis.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3248982PMC
http://dx.doi.org/10.1016/j.bmcl.2011.11.025DOI Listing

Publication Analysis

Top Keywords

macrocyclic diarylether
8
diarylether heptanoid
8
natural products
8
synthesis evaluation
4
evaluation macrocyclic
4
heptanoid natural
4
products analogs
4
analogs macrocyclic
4
heptanoid mdeh
4
mdeh natural
4

Similar Publications

Recent Advances in the Synthesis of Diarylheptanoids.

Chem Asian J

August 2024

Kasireddy Sudarshan, Suresh Yarlagadda, Sagnik Sengupta, Department of Chemistry, Institute for Drug Discovery, Purdue University, West Lafayette, IN-47907, USA.

In the quest for synthesizing biologically important natural products, medicinal chemists embark on an endless journey. This review focuses on the reports published towards the syntheses of diarylheptanoids, classifying them into linear, tetrahydropyran, diarylether, and biphenyl categories. The synthesis methods for each class from 2013 to 2023 are discussed, providing a comprehensive overview of the advancements in the field.

View Article and Find Full Text PDF

The macrocyclic diarylether heptanoid (MDEH) natural products have been used in folk medicine for centuries. MDEHs are reported to exert anti-tumor properties by inhibiting the activation of NF-κB. Here we report the synthesis of a small MDEH library (first reported synthesis of racemic platycarynol) using a Grubbs cross metathesis/Ullmann cyclization strategy.

View Article and Find Full Text PDF
Article Synopsis
  • - Isoriccardin C (1) and riccardin D (2) were isolated from the liverwort Reboulia hemisphaerica and found to exist as a mixture of two enantiomeric atropisomers.
  • - The characterization of these compounds was conducted using online chiral high-performance liquid chromatography-circular dichroism (HPLC-CD) analysis.
  • - Their absolute atropisomeric configurations were determined through the analysis of CD data combined with quantum chemical calculations.
View Article and Find Full Text PDF

The synthesis and structural analysis, involving X-ray crystallographic, nuclear magnetic resonance, and computational studies of four diastereomers of the common western BCD diarylether macrocycle of the complestatins, a family of HIV entry inhibitors, has been achieved exploiting a ruthenium-promoted intramolecular S(N)Ar reaction. The stereogenicity of the individual phenylglycines (residues C and D) results in remarkable effects on the backbone conformation.

View Article and Find Full Text PDF

Conformational analysis of marchantin A (1), a bis(diarylether) type, and riccardin A (2), a diarylether-biphenyl type macrocyclic bis(bibenzyl) was carried out by systematic unbounded multiple minimum search (SUMM). Mobility of the macrocyclic rings was analysed by variable temperature 1H-NMR study. Molecular similarity analysis was performed on the minimum energy conformers of 1 and 2 comparing their steric, electrostatic and hydrophobic properties.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!