345265-55-6

Basic information

• Product Name: 1-(piperazin-1-yl)-9,10-anthraquinone
• CAS NO: 345265-55-6
• Molecular Weight: 292.337
• Mol File: 345265-55-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-(piperazin-1-yl)-9,10-anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(piperazin-1-yl)-9,10-anthraquinone(345265-55-6)
• EPA Substance Registry System: 1-(piperazin-1-yl)-9,10-anthraquinone(345265-55-6)

Safety Data

• Hazardous Substances Data: 345265-55-6(Hazardous Substances Data)

Usage

Synonym

BBR 3464

Chemical class

Anthraquinone-containing compound

Potential therapeutic applications

Anti-cancer properties
Anti-malarial properties

Mechanism of action (anti-cancer)

Induces DNA damage in cancer cells
Inhibits topoisomerase II, an enzyme involved in DNA replication and repair

Mechanism of action (anti-malarial)

Disrupts the function of parasite mitochondria

Current status

Subject of ongoing research for the development of novel treatments for cancer and malaria

Upstream product

• 110-85-0 piperazine 
• 82-34-8 1-nitroanthraquinone 
• 82-44-0 1-chloroanthracene-9,10-dione 
• 142-63-2 piperazine hexahydrate 

Relevant articles and documents

Hydrogen bonding and protonation effects in amino acids' anthraquinone derivatives - Spectroscopic and electrochemical studies

Six novel amino acid chromophores were synthesized and their spectroscopic, acid-base, and electrochemical properties are discussed in this work. In studied compounds, selected amino acid residues (L-Aspartic acid, L-Glutamic acid, L-Glutamine, L-Histidine, L-Lysine, L-Arginine) are attached to the 1-(piperazine) 9,10-anthraquinone skeleton via the amide bond between the carboxyl group of amino acid and nitrogen atom of the piperazine ring. All derivatives have been characterized using a variety of spectroscopic techniques (mass spectrometry, 1HNMR, UV–Vis, IR spectroscopy), acid-base (electrochemical and UV–Vis) titrations, and cyclic voltammetry methods. Basing on observed experimental effects, supported by quantum chemical simulations, the structure-properties links were established. They are indicative of the specific interactions within and/or in-between amino acid side groups, which are prone to form both, intra- and intermolecular hydrogen bonds as well as electrostatic interactions with the anthraquinone system.