Synthesis and evaluation of a cyclopropane derivative of DHMEQ

Eiko Yasui; Kan Takayama; Takahiro Nakago; Nobuyuki Takeda; Yasutada Imamura; Shinji Nagumo

doi:10.1248/cpb.c13-00914

This article has now been updated. Please use the final version.

Synthesis and evaluation of a cyclopropane derivative of DHMEQ

Eiko Yasui, Kan Takayama, Takahiro Nakago, Nobuyuki Takeda, Yasutada Imamura, Shinji Nagumo

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Keywords: DHMEQ, cyclopropane, NF-κB, COX-2, RAW264.7

JOURNAL FREE ACCESS Advance online publication

Article ID: c13-00914

DOI https://doi.org/10.1248/cpb.c13-00914

The final version of this article is now available: Vol. 62 (2014), No. 3 pp. 304-307

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Abstract

DHMEQ (1) is well known to inhibit NF-κB, which is closely associated with immune, inflammatory, and apoptotic processes as an inducible transcription factor. The inhibitory effect seems to be the result of the ring opening of an epoxide of 1 with Cys³⁸ of p65. We have synthesized an analog 4 containing a cyclopropanated quinol skeleton and examined its ability to inhibit NF-κB. Surprisingly, 4 showed no remarkable NF-κB inhibitory activity as determined through expression of COX-2 in an RAW264.7 macrophage cell line.

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