287194-30-3Relevant articles and documents
Preparation and biological activities of optically active dehydroxymethylepoxyquinomicin, a novel NF-κB inhibitor
Suzuki, Yoshikazu,Sugiyama, Chie,Ohno, Osamu,Umezawa, Kazuo
, p. 7061 - 7066 (2004)
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
Synthesis of NF-κB activation inhibitors derived from epoxyquinomicin C
Matsumoto, Naoki,Ariga, Akiko,To-E, Sakino,Nakamura, Hikaru,Agata, Naoki,Hirano, Shin-Ichi,Inoue, Jun-Ichiro,Umezawa, Kazuo
, p. 865 - 869 (2007/10/03)
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.