2783-57-5

Usage

Uses

Used in Organic Synthesis:
2-Amino-1,4-benzoquinone is utilized as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the creation of a range of organic compounds.
Used in Dye and Pigment Production:
As a precursor, 2-Amino-1,4-benzoquinone is instrumental in the production of dyes and pigments, contributing to the coloration of different materials in industries such as textiles, plastics, and paints.
Used in Pharmaceutical Industry:
2-Amino-1,4-benzoquinone is used as a starting material in the synthesis of pharmaceuticals, highlighting its importance in the development of new drugs and therapeutic agents.
Used in Cancer Therapy Research:
In the field of oncology, 2-Amino-1,4-benzoquinone is studied for its potential application in cancer therapy, where it may contribute to the development of novel treatment strategies targeting cancer cells.
While the provided materials do not specify different applications across various industries, the uses listed above encompass the general applications of 2-Amino-1,4-benzoquinone based on its properties and known uses in chemical and pharmaceutical research.

Upstream product

• 106-51-4 p-benzoquinone 

Relevant academic research and scientific papers

Design of a hydrogen peroxide-activatable agent that specifically targets cancer cells

Some cancers, like acute myeloid leukemia (AML), use reactive oxygen species to endogenously activate cell proliferation and angiogenic signaling cascades. Thus many cancers display increases in reactive oxygen like hydrogen peroxide concentrations. To translate this finding into a therapeutic strategy we designed new hydrogen peroxide-activated agents with two key molecular pharmacophores. The first pharmacophore is a peroxide-acceptor and the second is a pendant amine. The acceptor is an N-(2,5-dihydroxyphenyl)acetamide susceptible to hydrogen peroxide oxidation. We hypothesized that selectivity between AML and normal cells could be achieved by tuning the pendant amine. Synthesis and testing of fourteen compounds that differed at the pendent amine led to the identification of an agent (14) with 2 μM activity against AML cancer cells and an eleven fold-lower activity in healthy CD34+ blood stem cells. Interestingly, analysis shows that upon oxidation the pendant amine cyclizes, ejecting water, with the acceptor to give a bicyclic compound capable of reacting with nucleophiles. Preliminary mechanistic investigations show that AML cells made from addition of two oncogenes (NrasG12D and MLL-AF9) increase the ROS-status, is initially an anti-oxidant as hydrogen peroxide is consumed to activate the pro-drug, and cells respond by upregulating electrophilic defense as visualized by Western blotting of KEAP1. Thus, using this chemical approach we have obtained a simple, potent, and selective ROS-activated anti-AML agent.