287194-40-5

Basic information

• Product Name: DEHYDROXYMETHYLEPOXYQUINOMICIN
• Synonyms: DEHYDROXYMETHYLEPOXYQUINOMICIN;DHM2EQ;DHMEQ;2-hydroxy-N-[(1S,2S,6S)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzaMide;Dehydroxymethylepoxyquinomicin (DHMEQ)
• CAS NO: 287194-40-5
• Molecular Formula: C₁₃H₁₁NO₅
• Molecular Weight: 261.23014
• Mol File: 287194-40-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DEHYDROXYMETHYLEPOXYQUINOMICIN(CAS DataBase Reference)
• NIST Chemistry Reference: DEHYDROXYMETHYLEPOXYQUINOMICIN(287194-40-5)
• EPA Substance Registry System: DEHYDROXYMETHYLEPOXYQUINOMICIN(287194-40-5)

Safety Data

• Hazardous Substances Data: 287194-40-5(Hazardous Substances Data)

Usage

General Description

DEHYDROXYMETHYLEPOXYQUINOMICIN is a potent antibiotic derived from the natural product epoxomicin. It is known for its ability to regulate the immune response and is being studied for its potential in cancer treatment and other immune-related diseases. The chemical compound acts by inhibiting the proteasome, a protein complex crucial for cell regulation and survival, thereby interfering with the growth and proliferation of cancer cells. DEHYDROXYMETHYLEPOXYQUINOMICIN has shown promising results in preclinical studies and is being further investigated for its therapeutic potential in various medical conditions.

Upstream product

• 287194-41-6 2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide 
• 287194-37-0 N-(2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide 
• 287194-32-5 N-(2,2-dimethoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide 
• 287194-30-3 acetic acid 2-(2,5-dimethoxyphenylcarbamoyl)phenyl ester 
• 287194-31-4 acetic acid 2-(6,6-dimethoxy-3-oxocyclohexa-1,4-dienylcarbamoyl)phenyl ester 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 1246285-28-8 (2S,3R)-2,3-epoxy-5-[(2-hydroxybenzoyl)amino]cyclohex-5-ene-1,4-dione 

Downstream Products

• 1192109-18-4 C₂₂H₂₈N₂O₉S 
• 1059670-12-0 C₂₀H₁₉NO₅S 
• 1192109-22-0 C₂₀H₁₉NO₅S 
• 1192109-21-9 C₁₅H₁₇NO₆S 
• 1192109-20-8 C₁₅H₁₇NO₆S 
• 1246285-32-4 (2S,3S,4S)-2,3-epoxy-4-hexanoyloxy-5-[(2-hexanoyloxybenzoyl)amino]cyclohex-5-en-1-one 
• 1059670-10-8 C₂₂H₂₈N₂O₉S 

Relevant articles and documents

Chemoenzymatic synthesis of (2S,3S,4S)-form, the physiologically active stereoisomer of dehydroxymethylepoxyquinomicin (DHMEQ), a potent inhibitor on NF-κB

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

Synthesis of NF-κB activation inhibitors derived from epoxyquinomicin C

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.