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

Vashti C. Bryant; G. D. Kishore Kumar; Abijah M. Nyong; Amarnath Natarajan

doi:10.1016/j.bmcl.2011.11.025

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

Vashti C. Bryant, G. D. Kishore Kumar, Abijah M. Nyong, Amarnath Natarajan

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	245-248
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	1
DOIs	https://doi.org/10.1016/j.bmcl.2011.11.025
State	Published - Jan 1 2012

Keywords

Grubbs/Ullmann
Macrocyclic diarylether heptanoid
NF-κB
Pancreatic cancer
Total synthesis

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2011.11.025

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title = "Synthesis and evaluation of macrocyclic diarylether heptanoid natural products and their analogs",

abstract = "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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AU - Natarajan, Amarnath

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

Abstract

Keywords

ASJC Scopus subject areas

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