Synthesis And Biological Evaluation Of Quinones Derivatives With Long Carbon Chain Cation

Quinones are a class of natural compound widely exist in bacteria and fungi,due to the hexanaphthene diketone structure,they are easier for redox reaction and play a role of transfering electron in biological metabolism process,hence,they show a variety of biological activity,including anti-cancer,anti-inflammatory and antioxidant and so on.In recent years,the research of antitumoractivity on emodin and naphthoquinone derivative are increasing.Emodin is a narural existing anthraquinone derivatives,it extracts from the roots and barks of many plants and molds,lichens,etc.Emodin can effectively suppresses the multiple cell signaling pathwanys,it can inhibit cell reproduction,invasion,metabolism angiogenesis.Emodin is a pleiotropic molecule that can interact with severalmajor molecular targets,including NF-kB,complex protein kinase II,topoisomerase II,p53,p21 and the male hormone receptor involved in inflammation andcancernThe previous study of antitumor activity on emodin quaternary ammonium salt show that the appropriate length and amount(8-10)of alkyl chain in the quatermary ammonium salt group are important to the cytotoxicity of the molecules.The confocal laser experiment of some compounds show that the emodinquaternary ammonium salt derivatives contain two long carbon chain mainly concentrated in the mitochondria,it prove that the targets of these compound is mitochondria.The mechanism may be the overproduction of ROS and cause tumor cell apoptosis.This paper summarizes the targetsof some anti-tumor and the related mechanism,including the low oxygen environment、HIF-1α、mitochondria and DNA,and also introduces several kinds of quinone derivatives,including emodin nitrogen oxides,2-methyl anthraquinone and naphthalene quinones quaternary ammonium salt and emodin platinum compounds.The structure of the new compounds in this paper were characterized by 1H NMR,ESI-MS,and a part of the compounds’ structure also confirmed by melting point,13C NMR and HRMS.Most of these compounds have been tested in HepG2 growth inhibitory of effects in vitro by MTT asssy.the results showed that the emodin tertiary amine、anthraquinones-quaternary ammonium salt and naphthalene quinones-quaternary ammonium salt containing two long alkyl chain has a good inhibitory activity on HepG2,and the quinone structure in the drug play a irreplaceable role in the process of inhibiting tumor cell growth.