- Chemoenzymatic synthesis of (2S,3S,4S)-form, the physiologically active stereoisomer of dehydroxymethylepoxyquinomicin (DHMEQ), a potent inhibitor on NF-κB
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A new route for (2S,3S,4S)-form, the physiologically active stereoisomer of dehydroxymethylepoxyquinomicin (DHMEQ), a potent NF-κB inhibitor, was established by chemoenzymatic approach. Elaboration on the asymmetric epoxidation of a p-benzoquinone monoket
- Hamada, Manabu,Niitsu, Yukihiro,Hiraoka, Chihiro,Kozawa, Ikuko,Higashi, Toshinori,Shoji, Mitsuru,Umezawa, Kazuo,Sugai, Takeshi
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p. 7083 - 7087
(2010/10/01)
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- Preparation and biological activities of optically active dehydroxymethylepoxyquinomicin, a novel NF-κB inhibitor
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NF-κB is a transcription factor that induces inflammatory cytokines and anti-apoptotic proteins. We have designed a new NF-κB inhibitor based on the structure of the antibiotic epoxyquinomicin C. The designed compound, dehydroxymethylepoxyquinomicin (DHME
- Suzuki, Yoshikazu,Sugiyama, Chie,Ohno, Osamu,Umezawa, Kazuo
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p. 7061 - 7066
(2007/10/03)
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- Synthesis of NF-κB activation inhibitors derived from epoxyquinomicin C
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In order to develop new inhibitors of NF-κB activation, we designed and synthesized dehydroxymethyl derivatives of epoxyquinomicin C, namely, DHM2EQ and its regioisomer DHM3EQ. These derivatives were synthesized from 2,5-dimethoxyaniline in 5 steps. Since DHM2EQ was more active and less toxic than DHM3EQ, its stereochemical configuration was determined by X-ray crystallographic analysis. Each enantiomer of the protected DHM2EQ was separated by a chiral column and deprotected. DHM2EQ inhibited TNF-α-induced activation of NF-κB in human T cell leukemia cells, and also inhibited collagen-induced arthritis in a rheumatoid model in mice. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Matsumoto, Naoki,Ariga, Akiko,To-E, Sakino,Nakamura, Hikaru,Agata, Naoki,Hirano, Shin-Ichi,Inoue, Jun-Ichiro,Umezawa, Kazuo
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p. 865 - 869
(2007/10/03)
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