Synthesis and antiproliferative activity of 1,4-bis(dimethylamino)-9,10-anthraquinone derivatives against P388 mouse leukemic tumor cells

Abstract

A series of 2-substituted-1,4-bis(dimethylamino)-9,10-anthraquinone derivatives were synthesized and their in vitro antiproliferative activities against p388 mouse leukemic tumor cells were evaluated. In addition, the effect of substituents on the phenyl ring was investigated. Among the derivatives tested, seven showed a high antiproliferative effect and three showed a moderate effect. In addition, introduction of a series of substituted phenyl groups into 1,4-bis(dimethylamino)-9,10-anthraquinone at 2-position were shown to enhance its antiproliferative activity. The antiproliferative activity also increased upon substitution of the benzene ring by an electron donating group such as an amine or methoxyl group.

Journey of anthraquinones as anticancer agents – a systematic review of recent literature

“…The analogue 29 showed an ED 50 value of 1.3 mg mL À1 while analogue 30 exhibited 1.5 mg mL À1 against the tested tumour cells. 59 Tu et al synthesized different anthraquinones derivatives that include 3-(3-alkylaminopropoxy)-9,10-anthraquinone and 1-hydroxy-3-(3-alkylaminopropoxy)-9,10-anthraquinone and evaluated their cytotoxicity towards different human cancer cell lines such as human urothelial carcinoma cells (NTUB1) and human prostate cancer cells (PC3). The derivatives 31 and 32 showed good anticancer activity against PC3 cells with IC 50 values of 7.64 and 8.89 mM, respectively.…”

“…The analogue 29 showed an ED 50 value of 1.3 μg mL −1 while analogue 30 exhibited 1.5 μg mL −1 against the tested tumour cells. 59 …”

Efficient amidation of weak amines: synthesis, chiral separation by SFC, and antimicrobial activity of N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) carboxamide

“…6 Several anthraquinone derivatives showing important biological activities have been reported. [7][8][9][10] Anthraquinone derivatives containing amines, amides, [11][12][13][14][15] pyrrole, and thiophene ring fused systems 16a show significantly increased cytotoxicity and are used as anti-proliferative agents in cancer therapy (Fig. 1).…”

The Phenolics from the Roots of Livistona chinensis Show Antioxidative and Obsteoblast Differentiation Promoting Activity

“…From the data above, phenolic 2 was identified as a new compound, anthracene-2,4,9-triol. The known phenolics were identified, by comparing of their spectroscopic data with data previously reported in the literature, as (−)-catechin ( 3 ) [14], (−)-epiafzelechin ( 4 ) [14], (−)-epicatechin ( 5 ) [18], (−)-afzelechin ( 6 ) [18], naphthalen-2-ol ( 7 ) [19] and 7-hydroxy-5,4'-dimethoxy-2-arylbenzofuran ( 8 ) [15].…”