Synthesis of DFGH-ring derivatives of physalins via one-pot construction of GH-ring and evaluation of their NF-κB-inhibitory activity

Makoto Yoritate; Yuki Morita; Manuel Gemander; Masaki Morita; Tomohiro Yamashita; Mikiko Sodeoka; Go Hirai

doi:10.1021/acs.orglett.0c03255

Synthesis of DFGH-ring derivatives of physalins via one-pot construction of GH-ring and evaluation of their NF-κB-inhibitory activity

Makoto Yoritate, Yuki Morita, Manuel Gemander, Masaki Morita, Tomohiro Yamashita, Mikiko Sodeoka, Go Hirai

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

3 Citations (Scopus)

Abstract

We designed and synthesized a series of derivatives containing the right-side DFGH-ring structure of physalin-type natural products, decorated with a hydrophobic substituent. The synthetic scheme utilizes a highly efficient, one-pot protocol for simultaneous construction of the GH-ring system, promoted by HF/pyridine. Among the compounds synthesized, 5d inhibited TNF-α-stimulated NF-κB activation with similar potency to physalin B.

Original language	English
Pages (from-to)	8877-8881
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.0c03255
Publication status	Published - Nov 20 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c03255

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abstract = "We designed and synthesized a series of derivatives containing the right-side DFGH-ring structure of physalin-type natural products, decorated with a hydrophobic substituent. The synthetic scheme utilizes a highly efficient, one-pot protocol for simultaneous construction of the GH-ring system, promoted by HF/pyridine. Among the compounds synthesized, 5d inhibited TNF-α-stimulated NF-κB activation with similar potency to physalin B.",

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AU - Yoritate, Makoto

AU - Morita, Yuki

AU - Gemander, Manuel

AU - Morita, Masaki

AU - Yamashita, Tomohiro

AU - Sodeoka, Mikiko

AU - Hirai, Go

PY - 2020/11/20

Y1 - 2020/11/20

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AB - We designed and synthesized a series of derivatives containing the right-side DFGH-ring structure of physalin-type natural products, decorated with a hydrophobic substituent. The synthetic scheme utilizes a highly efficient, one-pot protocol for simultaneous construction of the GH-ring system, promoted by HF/pyridine. Among the compounds synthesized, 5d inhibited TNF-α-stimulated NF-κB activation with similar potency to physalin B.

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Synthesis of DFGH-ring derivatives of physalins via one-pot construction of GH-ring and evaluation of their NF-κB-inhibitory activity

Abstract

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