Synthesis and evaluation of macrocyclic diarylether heptanoid natural products and their analogs

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...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2012-01, Vol.22 (1), p.245-248
Hauptverfasser:	Bryant, Vashti C., Kishore Kumar, G.D., Nyong, Abijah M., Natarajan, Amarnath
Format:	Artikel
Sprache:	eng
Schlagworte:	Antineoplastic Agents - pharmacology Apoptosis Biological and medical sciences Biological Products - chemistry Biological Products - pharmacology Cell Line Chemistry, Pharmaceutical - methods Drug Design Ether - analogs & derivatives Grubbs/Ullmann HEK293 Cells Humans Macrocyclic diarylether heptanoid Medical sciences Models, Chemical NF-kappa B - metabolism NF-κB Pancreatic cancer pancreatic neoplasms Pancreatic Neoplasms - drug therapy Pharmacology. Drug treatments Time Factors Total synthesis traditional medicine transcription factor NF-kappa B Tumor Necrosis Factor-alpha - metabolism
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Zusammenfassung:	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.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2011.11.025