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.
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http://dx.doi.org/10.1016/j.bmcl.2011.11.025 | DOI Listing |
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 PDFBioorg Med Chem Lett
January 2012
Eppley Institute for Cancer Research, University of Nebraska Medical Center, Omaha, NE 68198, USA.
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 PDFJ Asian Nat Prod Res
April 2011
School of Pharmaceutical Sciences, Shandong University, Jinan, China.
Bioorg Med Chem Lett
April 2004
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA.
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 PDFJ Mol Recognit
January 1997
Department of Chemical Information Technology, Technical University of Budapest, Hungary.
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.
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